# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_lhk-18l-2
_database_code_depnum_ccdc_archive 'CCDC 2106078'
loop_
_audit_author_name
_audit_author_address
'Zhaojiang Shi'
;FuZhou University
China
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-08-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 O3 S'
_chemical_formula_sum            'C16 H12 O3 S'
_chemical_formula_weight         284.32
_chemical_melting_point          ?
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'
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                   10.5967(12)
_cell_length_b                   8.9452(8)
_cell_length_c                   14.5399(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.211(4)
_cell_angle_gamma                90
_cell_volume                     1377.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.084
_cell_measurement_theta_min      2.804
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1371 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.7579.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43012
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.761
_diffrn_reflns_theta_min         1.923
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             3876
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.041
_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)+(0.0748P)²+1.8185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 S1, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C16(H008), C12(H00B), C8(H00D), C15(H00E), C7(H00F), C5(H00G), C13(H00H),
 C14(H00J), C6(H00K)
3.b Idealised Me refined as rotating group:
 C10(H00A,H00C,H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42382(7) 0.14441(9) 0.59064(6) 0.0392(2) Uani 1 1 d . U . . .
O1 O 0.0912(2) 0.2687(2) 0.51584(13) 0.0345(5) Uani 1 1 d . U . . .
O2 O 0.24030(18) 0.00351(19) 0.48843(13) 0.0301(4) Uani 1 1 d . . . . .
O3 O 0.3021(2) 0.1792(2) 0.39034(14) 0.0389(5) Uani 1 1 d . . . . .
C11 C 0.1900(2) 0.0334(3) 0.64393(18) 0.0282(6) Uani 1 1 d . . . . .
C9 C 0.2691(2) 0.0531(3) 0.40393(18) 0.0299(6) Uani 1 1 d . . . . .
C1 C 0.2537(3) 0.1062(3) 0.56394(18) 0.0294(5) Uani 1 1 d . U . . .
C16 C 0.2206(3) 0.0784(3) 0.73352(19) 0.0348(6) Uani 1 1 d . . . . .
H008 H 0.282196 0.150969 0.744440 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2732(3) 0.3852(3) 0.56760(18) 0.0303(6) Uani 1 1 d . . . . .
C2 C 0.1877(3) 0.2599(3) 0.54215(19) 0.0333(5) Uani 1 1 d . U . . .
C12 C 0.0962(3) -0.0729(3) 0.6284(2) 0.0343(6) Uani 1 1 d . . . . .
H00B H 0.073197 -0.101416 0.568532 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3937(3) 0.3392(3) 0.59384(19) 0.0342(6) Uani 1 1 d . U . . .
C8 C 0.2422(3) 0.5370(3) 0.56517(19) 0.0343(6) Uani 1 1 d . . . . .
H00D H 0.161025 0.567856 0.547484 0.041 Uiso 1 1 calc R U . . .
C15 C 0.1594(3) 0.0154(3) 0.8066(2) 0.0409(7) Uani 1 1 d . . . . .
H00E H 0.179929 0.045860 0.866477 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3343(3) 0.6402(3) 0.5895(2) 0.0391(7) Uani 1 1 d . . . . .
H00F H 0.315968 0.741849 0.587431 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4857(3) 0.4425(4) 0.6199(2) 0.0391(7) Uani 1 1 d . . . . .
H00G H 0.566479 0.411877 0.638667 0.047 Uiso 1 1 calc R U . . .
C13 C 0.0372(3) -0.1364(4) 0.7019(2) 0.0427(7) Uani 1 1 d . . . . .
H00H H -0.024054 -0.209457 0.691247 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2521(3) -0.0676(4) 0.3335(2) 0.0424(7) Uani 1 1 d . . . . .
H00A H 0.281541 -0.160835 0.359054 0.064 Uiso 1 1 calc R U . . .
H00C H 0.299602 -0.043465 0.280582 0.064 Uiso 1 1 calc R U . . .
H00I H 0.164251 -0.076184 0.315550 0.064 Uiso 1 1 calc R U . . .
C14 C 0.0681(3) -0.0927(3) 0.7906(2) 0.0427(8) Uani 1 1 d . . . . .
H00J H 0.027583 -0.135728 0.839613 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4543(3) 0.5922(3) 0.6171(2) 0.0422(7) Uani 1 1 d . . . . .
H00K H 0.515174 0.662789 0.634284 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.861(3) . ?
S1 C4 1.772(3) . ?
O1 C2 1.081(4) . ?
O2 C9 1.352(3) . ?
O2 C1 1.434(3) . ?
O3 C9 1.200(3) . ?
C11 C1 1.514(4) . ?
C11 C16 1.390(4) . ?
C11 C12 1.387(4) . ?
C9 C10 1.495(4) . ?
C1 C2 1.569(4) . ?
C16 H008 0.9300 . ?
C16 C15 1.385(4) . ?
C3 C2 1.479(4) . ?
C3 C4 1.382(4) . ?
C3 C8 1.397(4) . ?
C12 H00B 0.9300 . ?
C12 C13 1.381(4) . ?
C4 C5 1.385(4) . ?
C8 H00D 0.9300 . ?
C8 C7 1.380(4) . ?
C15 H00E 0.9300 . ?
C15 C14 1.382(5) . ?
C7 H00F 0.9300 . ?
C7 C6 1.386(5) . ?
C5 H00G 0.9300 . ?
C5 C6 1.380(5) . ?
C13 H00H 0.9300 . ?
C13 C14 1.375(5) . ?
C10 H00A 0.9600 . ?
C10 H00C 0.9600 . ?
C10 H00I 0.9600 . ?
C14 H00J 0.9300 . ?
C6 H00K 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
C4 S1 C1 90.70(13) . . ?
C9 O2 C1 117.8(2) . . ?
C16 C11 C1 120.0(2) . . ?
C12 C11 C1 120.5(2) . . ?
C12 C11 C16 119.4(3) . . ?
O2 C9 C10 111.1(2) . . ?
O3 C9 O2 122.4(2) . . ?
O3 C9 C10 126.5(3) . . ?
O2 C1 S1 110.08(18) . . ?
O2 C1 C11 106.2(2) . . ?
O2 C1 C2 112.1(2) . . ?
C11 C1 S1 112.07(19) . . ?
C11 C1 C2 108.9(2) . . ?
C2 C1 S1 107.55(18) . . ?
C11 C16 H008 119.9 . . ?
C15 C16 C11 120.1(3) . . ?
C15 C16 H008 119.9 . . ?
C4 C3 C2 113.2(2) . . ?
C4 C3 C8 120.7(3) . . ?
C8 C3 C2 126.1(3) . . ?
O1 C2 C1 122.9(3) . . ?
O1 C2 C3 126.6(3) . . ?
C3 C2 C1 110.5(3) . . ?
C11 C12 H00B 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H00B 120.1 . . ?
C3 C4 S1 116.8(2) . . ?
C3 C4 C5 120.6(3) . . ?
C5 C4 S1 122.6(2) . . ?
C3 C8 H00D 120.6 . . ?
C7 C8 C3 118.7(3) . . ?
C7 C8 H00D 120.6 . . ?
C16 C15 H00E 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H00E 120.0 . . ?
C8 C7 H00F 120.0 . . ?
C8 C7 C6 119.9(3) . . ?
C6 C7 H00F 120.0 . . ?
C4 C5 H00G 120.9 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H00G 120.9 . . ?
C12 C13 H00H 119.7 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H00H 119.7 . . ?
C9 C10 H00A 109.5 . . ?
C9 C10 H00C 109.5 . . ?
C9 C10 H00I 109.5 . . ?
H00A C10 H00C 109.5 . . ?
H00A C10 H00I 109.5 . . ?
H00C C10 H00I 109.5 . . ?
C15 C14 H00J 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H00J 120.1 . . ?
C7 C6 H00K 119.1 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H00K 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 O1 171.8(2) . . . . ?
S1 C1 C2 C3 -11.4(3) . . . . ?
S1 C4 C5 C6 177.8(2) . . . . ?
O2 C1 C2 O1 50.7(4) . . . . ?
O2 C1 C2 C3 -132.5(2) . . . . ?
C11 C1 C2 O1 -66.5(3) . . . . ?
C11 C1 C2 C3 110.3(2) . . . . ?
C11 C16 C15 C14 0.2(4) . . . . ?
C11 C12 C13 C14 1.6(5) . . . . ?
C9 O2 C1 S1 -70.2(3) . . . . ?
C9 O2 C1 C11 168.3(2) . . . . ?
C9 O2 C1 C2 49.5(3) . . . . ?
C1 S1 C4 C3 -6.8(2) . . . . ?
C1 S1 C4 C5 174.1(2) . . . . ?
C1 O2 C9 O3 -1.7(4) . . . . ?
C1 O2 C9 C10 179.1(2) . . . . ?
C1 C11 C16 C15 177.9(3) . . . . ?
C1 C11 C12 C13 -178.8(3) . . . . ?
C16 C11 C1 S1 38.7(3) . . . . ?
C16 C11 C1 O2 159.0(2) . . . . ?
C16 C11 C1 C2 -80.1(3) . . . . ?
C16 C11 C12 C13 -2.1(4) . . . . ?
C16 C15 C14 C13 -0.6(5) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C3 C8 C7 C6 -1.0(4) . . . . ?
C2 C3 C4 S1 0.9(3) . . . . ?
C2 C3 C4 C5 180.0(3) . . . . ?
C2 C3 C8 C7 -178.7(3) . . . . ?
C12 C11 C1 S1 -144.6(2) . . . . ?
C12 C11 C1 O2 -24.4(3) . . . . ?
C12 C11 C1 C2 96.6(3) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C4 S1 C1 O2 132.38(19) . . . . ?
C4 S1 C1 C11 -109.68(19) . . . . ?
C4 S1 C1 C2 9.96(19) . . . . ?
C4 C3 C2 O1 -176.2(3) . . . . ?
C4 C3 C2 C1 7.1(3) . . . . ?
C4 C3 C8 C7 0.0(4) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C8 C3 C2 O1 2.5(5) . . . . ?
C8 C3 C2 C1 -174.1(3) . . . . ?
C8 C3 C4 S1 -177.9(2) . . . . ?
C8 C3 C4 C5 1.2(4) . . . . ?
C8 C7 C6 C5 1.0(5) . . . . ?

_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_lhk-2oy-2
_database_code_depnum_ccdc_archive 'CCDC 2106081'
loop_
_audit_author_name
_audit_author_address
'Zhaojiang Shi'
;FuZhou University
China
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-08-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 O4 S'
_chemical_formula_sum            'C14 H12 O4 S'
_chemical_formula_weight         276.30
_chemical_melting_point          ?
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'
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                   6.6773(4)
_cell_length_b                   8.2045(4)
_cell_length_c                   12.3368(8)
_cell_angle_alpha                103.440(2)
_cell_angle_beta                 98.505(2)
_cell_angle_gamma                98.528(2)
_cell_volume                     638.29(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6965
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.629
_cell_measurement_theta_min      2.599
_shelx_estimated_absorpt_T_max   0.881
_shelx_estimated_absorpt_T_min   0.781
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.9547.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33443
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.774
_diffrn_reflns_theta_min         1.729
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2993
_reflns_number_total             4662
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.032
_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)+(0.0409P)²+0.1324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1040
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C2(H2), C10(H10), C12(H12), C3(H3)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50768(6) 0.44952(5) 0.82841(3) 0.02381(10) Uani 1 1 d . . . . .
O2 O 0.46883(14) 0.78271(12) 0.86325(8) 0.0196(2) Uani 1 1 d . . . . .
O3 O 0.76268(15) 0.74816(13) 0.79995(9) 0.0266(2) Uani 1 1 d . . . . .
O4 O 0.27760(19) 1.05016(13) 0.56485(10) 0.0371(3) Uani 1 1 d . . . . .
O1 O 0.28826(19) 0.20656(14) 0.89448(10) 0.0394(3) Uani 1 1 d . . . . .
C5 C 0.6665(2) 0.83881(18) 0.85437(12) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.2880(2) 0.45365(17) 0.58680(12) 0.0199(3) Uani 1 1 d . . . . .
H8 H 0.294761 0.352847 0.608227 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2390(2) 0.44903(17) 0.47299(12) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.212611 0.345092 0.418417 0.025 Uiso 1 1 calc R U . . .
C2 C 0.1660(2) 0.58040(18) 0.83402(12) 0.0218(3) Uani 1 1 d . . . . .
H2 H 0.073492 0.654601 0.833062 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3275(2) 0.60866(16) 0.66960(11) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.2290(2) 0.59780(17) 0.43993(12) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.199207 0.594248 0.363255 0.025 Uiso 1 1 calc R U . . .
C1 C 0.3691(2) 0.61418(17) 0.79576(12) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.3115(2) 0.75730(17) 0.63623(12) 0.0197(3) Uani 1 1 d . . . . .
H12 H 0.332984 0.860654 0.690986 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2637(2) 0.75361(17) 0.52187(12) 0.0196(3) Uani 1 1 d . . . . .
C13 C 0.2493(2) 0.91749(18) 0.49090(13) 0.0252(3) Uani 1 1 d . . . . .
C4 C 0.2916(2) 0.34092(19) 0.87011(13) 0.0271(3) Uani 1 1 d . . . . .
C3 C 0.1255(2) 0.44071(19) 0.86890(13) 0.0268(3) Uani 1 1 d . . . . .
H3 H 0.001760 0.407853 0.891007 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7407(2) 1.02001(18) 0.91945(13) 0.0266(3) Uani 1 1 d . . . . .
H6A H 0.645033 1.087876 0.896767 0.040 Uiso 1 1 calc R U . . .
H6B H 0.873620 1.060531 0.904507 0.040 Uiso 1 1 calc R U . . .
H6C H 0.751392 1.028640 0.999127 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1986(3) 0.9156(2) 0.36781(14) 0.0354(4) Uani 1 1 d . . . . .
H14A H 0.204830 1.030412 0.361154 0.053 Uiso 1 1 calc R U . . .
H14B H 0.062174 0.850751 0.335446 0.053 Uiso 1 1 calc R U . . .
H14C H 0.296231 0.864311 0.328166 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.8324(13) . ?
S1 C4 1.7863(16) . ?
O2 C5 1.3610(16) . ?
O2 C1 1.4410(16) . ?
O3 C5 1.2055(16) . ?
O4 C13 1.2162(18) . ?
O1 C4 1.2061(18) . ?
C5 C6 1.486(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(2) . ?
C8 C7 1.3955(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.5089(19) . ?
C2 C3 1.320(2) . ?
C7 C1 1.5288(19) . ?
C7 C12 1.3882(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.3919(19) . ?
C11 C13 1.4931(19) . ?
C13 C14 1.502(2) . ?
C4 C3 1.473(2) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C4 S1 C1 92.97(7) . . ?
C5 O2 C1 117.41(10) . . ?
O2 C5 C6 111.11(12) . . ?
O3 C5 O2 122.23(13) . . ?
O3 C5 C6 126.66(13) . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.39(12) . . ?
C7 C8 H8 119.8 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.43(12) . . ?
C10 C9 H9 119.8 . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C3 C2 C1 116.98(13) . . ?
C8 C7 C1 120.82(11) . . ?
C12 C7 C8 119.00(13) . . ?
C12 C7 C1 119.96(12) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.89(13) . . ?
C11 C10 H10 120.1 . . ?
O2 C1 S1 112.11(9) . . ?
O2 C1 C2 105.08(10) . . ?
O2 C1 C7 110.89(10) . . ?
C2 C1 S1 105.39(9) . . ?
C2 C1 C7 109.08(11) . . ?
C7 C1 S1 113.72(9) . . ?
C7 C12 H12 119.6 . . ?
C7 C12 C11 120.84(12) . . ?
C11 C12 H12 119.6 . . ?
C10 C11 C13 122.06(13) . . ?
C12 C11 C10 119.41(12) . . ?
C12 C11 C13 118.53(12) . . ?
O4 C13 C11 120.06(14) . . ?
O4 C13 C14 120.82(13) . . ?
C11 C13 C14 119.12(13) . . ?
O1 C4 S1 123.54(13) . . ?
O1 C4 C3 127.12(15) . . ?
C3 C4 S1 109.34(10) . . ?
C2 C3 C4 114.83(13) . . ?
C2 C3 H3 122.6 . . ?
C4 C3 H3 122.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 2.64(17) . . . . ?
O1 C4 C3 C2 -177.14(16) . . . . ?
C5 O2 C1 S1 59.27(13) . . . . ?
C5 O2 C1 C2 173.24(11) . . . . ?
C5 O2 C1 C7 -69.03(14) . . . . ?
C8 C9 C10 C11 -1.5(2) . . . . ?
C8 C7 C1 S1 34.06(15) . . . . ?
C8 C7 C1 O2 161.49(11) . . . . ?
C8 C7 C1 C2 -83.25(15) . . . . ?
C8 C7 C12 C11 -2.1(2) . . . . ?
C9 C8 C7 C1 176.30(12) . . . . ?
C9 C8 C7 C12 1.67(19) . . . . ?
C9 C10 C11 C12 1.1(2) . . . . ?
C9 C10 C11 C13 -178.36(13) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C7 C12 C11 C10 0.8(2) . . . . ?
C7 C12 C11 C13 -179.77(12) . . . . ?
C10 C11 C13 O4 178.92(14) . . . . ?
C10 C11 C13 C14 -0.8(2) . . . . ?
C1 S1 C4 O1 174.41(14) . . . . ?
C1 S1 C4 C3 -5.38(11) . . . . ?
C1 O2 C5 O3 -5.98(19) . . . . ?
C1 O2 C5 C6 174.20(11) . . . . ?
C1 C2 C3 C4 2.65(19) . . . . ?
C1 C7 C12 C11 -176.82(12) . . . . ?
C12 C7 C1 S1 -151.36(11) . . . . ?
C12 C7 C1 O2 -23.93(16) . . . . ?
C12 C7 C1 C2 91.33(15) . . . . ?
C12 C11 C13 O4 -0.5(2) . . . . ?
C12 C11 C13 C14 179.78(14) . . . . ?
C4 S1 C1 O2 120.16(10) . . . . ?
C4 S1 C1 C2 6.38(10) . . . . ?
C4 S1 C1 C7 -113.04(10) . . . . ?
C3 C2 C1 S1 -6.39(15) . . . . ?
C3 C2 C1 O2 -124.98(13) . . . . ?
C3 C2 C1 C7 116.07(14) . . . . ?

_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_1234
_database_code_depnum_ccdc_archive 'CCDC 2106079'
loop_
_audit_author_name
_audit_author_address
'Zhaojiang Shi'
;FuZhou University
China
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-08-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 N O3 S'
_chemical_formula_sum            'C15 H11 N O3 S'
_chemical_formula_weight         285.31
_chemical_melting_point          ?
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'
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                   11.5157(9)
_cell_length_b                   7.2349(5)
_cell_length_c                   15.7485(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.933(3)
_cell_angle_gamma                90
_cell_volume                     1305.06(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4191
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1093 before and 0.0683 after correction.
The Ratio of minimum to maximum transmission is 0.8066.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_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  0.1174
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30687
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.601
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1491
_reflns_number_total             2304
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0476
_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)+(0.0562P)²+0.3923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C10(H10), C9(H9), C3(H3), C14(H14), C15(H15), C2(H2)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17052(7) 0.52791(11) 0.76211(5) 0.0568(3) Uani 1 1 d . . . . .
O2 O 0.15718(16) 0.4940(2) 0.59110(12) 0.0463(5) Uani 1 1 d . . . . .
O3 O 0.2228(2) 0.7770(3) 0.62794(14) 0.0589(6) Uani 1 1 d . . . . .
N1 N 0.5800(2) 0.2695(3) 0.52695(16) 0.0487(6) Uani 1 1 d . . . . .
C7 C 0.3511(2) 0.4211(3) 0.66352(17) 0.0375(7) Uani 1 1 d . . . . .
C12 C 0.4002(2) 0.3449(3) 0.59106(16) 0.0365(6) Uani 1 1 d . . . . .
C11 C 0.5242(2) 0.3385(3) 0.59280(17) 0.0404(7) Uani 1 1 d . . . . .
C4 C 0.2191(2) 0.4171(4) 0.66774(17) 0.0403(7) Uani 1 1 d . . . . .
C8 C 0.4251(2) 0.4860(4) 0.73059(17) 0.0415(7) Uani 1 1 d . . . . .
H8 H 0.393558 0.536425 0.777458 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3359(3) 0.2738(4) 0.51639(17) 0.0449(7) Uani 1 1 d . . . . .
H13 H 0.254741 0.273820 0.511446 0.054 Uiso 1 1 calc R U . . .
O1 O 0.0798(2) 0.3059(4) 0.87061(17) 0.1001(10) Uani 1 1 d . . . . .
C10 C 0.5945(2) 0.4066(4) 0.66390(19) 0.0457(7) Uani 1 1 d . . . . .
H10 H 0.675364 0.401832 0.664899 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5462(3) 0.4789(4) 0.73082(18) 0.0463(7) Uani 1 1 d . . . . .
H9 H 0.593844 0.524329 0.777439 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1782(2) 0.2173(4) 0.6725(2) 0.0467(7) Uani 1 1 d . . . . .
H3 H 0.185472 0.133874 0.628459 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1716(3) 0.6788(4) 0.5767(2) 0.0487(8) Uani 1 1 d . . . . .
C14 C 0.3934(3) 0.2062(4) 0.45257(19) 0.0514(8) Uani 1 1 d . . . . .
H14 H 0.351761 0.159317 0.403521 0.062 Uiso 1 1 calc R U . . .
C15 C 0.5146(3) 0.2067(4) 0.4602(2) 0.0539(8) Uani 1 1 d . . . . .
H15 H 0.551583 0.159581 0.415123 0.065 Uiso 1 1 calc R U . . .
C2 C 0.1326(3) 0.1696(5) 0.7414(2) 0.0636(10) Uani 1 1 d . . . . .
H2 H 0.110239 0.048677 0.751280 0.076 Uiso 1 1 calc R U . . .
C1 C 0.1191(3) 0.3173(5) 0.8016(2) 0.0672(10) Uani 1 1 d . . . . .
C6 C 0.1150(3) 0.7314(5) 0.4910(2) 0.0685(10) Uani 1 1 d . . . . .
H6A H 0.141317 0.650290 0.448703 0.103 Uiso 1 1 calc R U . . .
H6B H 0.135349 0.856476 0.478549 0.103 Uiso 1 1 calc R U . . .
H6C H 0.031795 0.721415 0.490388 0.103 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.827(3) . ?
S1 C1 1.771(4) . ?
O2 C4 1.448(3) . ?
O2 C5 1.369(3) . ?
O3 C5 1.185(3) . ?
N1 C11 1.369(3) . ?
N1 C15 1.310(4) . ?
C7 C12 1.435(4) . ?
C7 C4 1.529(4) . ?
C7 C8 1.370(4) . ?
C12 C11 1.427(4) . ?
C12 C13 1.420(4) . ?
C11 C10 1.402(4) . ?
C4 C3 1.525(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.396(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.351(4) . ?
O1 C1 1.222(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.347(4) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.298(4) . ?
C5 C6 1.487(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(4) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.448(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
C1 S1 C4 92.86(15) . . ?
C5 O2 C4 117.1(2) . . ?
C15 N1 C11 117.3(3) . . ?
C12 C7 C4 120.2(2) . . ?
C8 C7 C12 118.7(2) . . ?
C8 C7 C4 121.0(2) . . ?
C11 C12 C7 118.3(2) . . ?
C13 C12 C7 125.7(2) . . ?
C13 C12 C11 116.1(2) . . ?
N1 C11 C12 123.0(3) . . ?
N1 C11 C10 117.1(3) . . ?
C10 C11 C12 119.9(2) . . ?
O2 C4 S1 110.11(17) . . ?
O2 C4 C7 111.3(2) . . ?
O2 C4 C3 106.1(2) . . ?
C7 C4 S1 114.62(18) . . ?
C3 C4 S1 104.70(19) . . ?
C3 C4 C7 109.5(2) . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 122.1(3) . . ?
C9 C8 H8 119.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C4 C3 H3 121.7 . . ?
C2 C3 C4 116.5(3) . . ?
C2 C3 H3 121.7 . . ?
O2 C5 C6 110.5(3) . . ?
O3 C5 O2 122.2(3) . . ?
O3 C5 C6 127.2(3) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
N1 C15 C14 124.1(3) . . ?
N1 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C3 C2 H2 122.2 . . ?
C3 C2 C1 115.6(3) . . ?
C1 C2 H2 122.2 . . ?
O1 C1 S1 122.6(3) . . ?
O1 C1 C2 127.4(4) . . ?
C2 C1 S1 110.0(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 -6.5(3) . . . . ?
O2 C4 C3 C2 -122.9(3) . . . . ?
N1 C11 C10 C9 179.1(2) . . . . ?
C7 C12 C11 N1 -179.7(2) . . . . ?
C7 C12 C11 C10 -0.4(4) . . . . ?
C7 C12 C13 C14 179.9(3) . . . . ?
C7 C4 C3 C2 116.9(3) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C12 C7 C4 S1 -177.63(19) . . . . ?
C12 C7 C4 O2 -51.9(3) . . . . ?
C12 C7 C4 C3 65.1(3) . . . . ?
C12 C7 C8 C9 -0.6(4) . . . . ?
C12 C11 C10 C9 -0.2(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C11 N1 C15 C14 0.0(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C11 C10 C9 C8 0.4(4) . . . . ?
C4 S1 C1 O1 175.9(3) . . . . ?
C4 S1 C1 C2 -3.4(2) . . . . ?
C4 O2 C5 O3 -7.2(4) . . . . ?
C4 O2 C5 C6 172.9(2) . . . . ?
C4 C7 C12 C11 -175.2(2) . . . . ?
C4 C7 C12 C13 4.7(4) . . . . ?
C4 C7 C8 C9 175.3(2) . . . . ?
C4 C3 C2 C1 4.4(4) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
C8 C7 C12 C13 -179.3(2) . . . . ?
C8 C7 C4 S1 6.6(3) . . . . ?
C8 C7 C4 O2 132.3(2) . . . . ?
C8 C7 C4 C3 -110.7(3) . . . . ?
C13 C12 C11 N1 0.4(4) . . . . ?
C13 C12 C11 C10 179.7(2) . . . . ?
C13 C14 C15 N1 0.2(5) . . . . ?
C3 C2 C1 S1 0.0(4) . . . . ?
C3 C2 C1 O1 -179.2(3) . . . . ?
C5 O2 C4 S1 61.6(3) . . . . ?
C5 O2 C4 C7 -66.6(3) . . . . ?
C5 O2 C4 C3 174.3(2) . . . . ?
C15 N1 C11 C12 -0.3(4) . . . . ?
C15 N1 C11 C10 -179.6(2) . . . . ?
C1 S1 C4 O2 118.8(2) . . . . ?
C1 S1 C4 C7 -114.8(2) . . . . ?
C1 S1 C4 C3 5.2(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_lhk-21z-1
_database_code_depnum_ccdc_archive 'CCDC 2106084'
loop_
_audit_author_name
_audit_author_address
'Zhaojiang Shi'
;FuZhou University
China
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-08-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 O3 S'
_chemical_formula_sum            'C18 H14 O3 S'
_chemical_formula_weight         310.35
_chemical_melting_point          ?
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'
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                   9.346(5)
_cell_length_b                   11.033(5)
_cell_length_c                   15.429(6)
_cell_angle_alpha                77.727(15)
_cell_angle_beta                 82.415(19)
_cell_angle_gamma                80.856(18)
_cell_volume                     1526.9(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.740
_cell_measurement_theta_min      2.221
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1648 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.6559.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            64650
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.245
_diffrn_reflns_theta_min         1.906
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6312
_reflns_number_total             9037
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         9037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.038
_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)+(0.0527P)²+0.3790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H00F), C18(H00G), C21(H00I), C17(H00M), C16(H00N), C14(H00O), C6(H00R),
 C15(H00S), C8(H00U), C7(H00V), C36(H00W), C32(H00X), C10(H00Y), C26(H00Z),
 C28(H011), C33(H012), C9(H013), C34(H014), C30(H015), C35(H016), C27(H017),
 C29(H018)
2.b Idealised Me refined as rotating group:
 C12(H00A,H00B,H00C), C24(H01A,H01B,H01C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.77487(4) 0.62904(4) 0.46124(3) 0.02316(10) Uani 1 1 d . . . . .
S2 S 0.68796(5) 0.34613(4) 0.03567(3) 0.02710(11) Uani 1 1 d . . . . .
O2 O 0.78766(12) 0.82118(10) 0.54282(7) 0.0223(2) Uani 1 1 d . . . . .
O1 O 0.80668(12) 0.98010(10) 0.36592(7) 0.0246(2) Uani 1 1 d . . . . .
O5 O 0.49168(12) 0.20860(11) 0.00375(7) 0.0269(3) Uani 1 1 d . . . . .
O3 O 0.56078(12) 0.86285(11) 0.50029(7) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.63641(14) -0.00265(11) 0.12540(8) 0.0326(3) Uani 1 1 d . . . . .
O6 O 0.40633(14) 0.22821(12) 0.14432(8) 0.0363(3) Uani 1 1 d . . . . .
C2 C 0.78908(16) 0.87040(14) 0.37793(10) 0.0197(3) Uani 1 1 d . . . . .
C5 C 0.64057(17) 0.60358(14) 0.31738(10) 0.0210(3) Uani 1 1 d . . . . .
C13 C 1.00688(17) 0.76291(14) 0.45538(10) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.64168(17) 0.86285(14) 0.55438(10) 0.0230(3) Uani 1 1 d . . . . .
C4 C 0.71040(16) 0.68752(14) 0.35624(10) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.84166(17) 0.77603(14) 0.46221(10) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.72730(17) 0.80843(14) 0.32112(10) 0.0213(3) Uani 1 1 d . . . . .
H00F H 0.701191 0.848309 0.264906 0.026 Uiso 1 1 calc R U . . .
C18 C 1.07586(17) 0.83008(15) 0.50031(10) 0.0237(3) Uani 1 1 d . . . . .
H00G H 1.020980 0.879880 0.537697 0.028 Uiso 1 1 calc R U . . .
C25 C 0.86478(18) 0.34659(15) 0.16783(11) 0.0255(3) Uani 1 1 d . . . . .
C21 C 0.75015(18) 0.15462(15) 0.16583(11) 0.0256(3) Uani 1 1 d . . . . .
H00I H 0.784142 0.108923 0.218771 0.031 Uiso 1 1 calc R U . . .
C31 C 0.73385(18) 0.14830(15) -0.05450(10) 0.0241(3) Uani 1 1 d . . . . .
C20 C 0.66974(18) 0.10281(15) 0.11191(10) 0.0248(3) Uani 1 1 d . . . . .
C22 C 0.77207(18) 0.27474(15) 0.13327(10) 0.0240(3) Uani 1 1 d . . . . .
C17 C 1.22683(18) 0.82280(15) 0.48935(11) 0.0269(4) Uani 1 1 d . . . . .
H00M H 1.272734 0.866940 0.520111 0.032 Uiso 1 1 calc R U . . .
C16 C 1.30911(18) 0.75028(15) 0.43294(11) 0.0280(4) Uani 1 1 d . . . . .
H00N H 1.410077 0.745745 0.425724 0.034 Uiso 1 1 calc R U . . .
C14 C 1.09051(18) 0.69028(16) 0.39833(11) 0.0273(4) Uani 1 1 d . . . . .
H00O H 1.045227 0.645606 0.367629 0.033 Uiso 1 1 calc R U . . .
C19 C 0.63945(17) 0.19620(15) 0.02297(10) 0.0235(3) Uani 1 1 d . . . . .
C23 C 0.38287(19) 0.22309(16) 0.07066(11) 0.0287(4) Uani 1 1 d . . . . .
C6 C 0.5901(2) 0.64268(16) 0.23371(11) 0.0301(4) Uani 1 1 d . . . . .
H00R H 0.604142 0.721477 0.200474 0.036 Uiso 1 1 calc R U . . .
C15 C 1.24082(19) 0.68452(16) 0.38730(12) 0.0305(4) Uani 1 1 d . . . . .
H00S H 1.296043 0.636217 0.349035 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6023(2) 0.90552(17) 0.64130(11) 0.0306(4) Uani 1 1 d . . . . .
H00A H 0.636265 0.984439 0.637045 0.046 Uiso 1 1 calc R U . . .
H00B H 0.646888 0.844657 0.687639 0.046 Uiso 1 1 calc R U . . .
H00C H 0.498358 0.914835 0.654978 0.046 Uiso 1 1 calc R U . . .
C8 C 0.49753(19) 0.44695(17) 0.24804(12) 0.0329(4) Uani 1 1 d . . . . .
H00U H 0.448982 0.395307 0.225178 0.040 Uiso 1 1 calc R U . . .
C7 C 0.5188(2) 0.56466(18) 0.19948(12) 0.0349(4) Uani 1 1 d . . . . .
H00V H 0.485137 0.591742 0.143560 0.042 Uiso 1 1 calc R U . . .
C36 C 0.6721(2) 0.10564(16) -0.11724(11) 0.0306(4) Uani 1 1 d . . . . .
H00W H 0.571994 0.104637 -0.112159 0.037 Uiso 1 1 calc R U . . .
C32 C 0.88426(19) 0.14530(17) -0.06165(12) 0.0321(4) Uani 1 1 d . . . . .
H00X H 0.926671 0.172109 -0.019070 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6195(2) 0.48433(16) 0.36522(12) 0.0339(4) Uani 1 1 d . . . . .
H00Y H 0.653168 0.456406 0.421080 0.041 Uiso 1 1 calc R U . . .
C26 C 0.9041(2) 0.45889(17) 0.11770(13) 0.0385(4) Uani 1 1 d . . . . .
H00Z H 0.866445 0.491870 0.063437 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2375(2) 0.23186(19) 0.03748(13) 0.0388(5) Uani 1 1 d . . . . .
H01A H 0.232557 0.292355 -0.017249 0.058 Uiso 1 1 calc R U . . .
H01B H 0.162041 0.257210 0.081178 0.058 Uiso 1 1 calc R U . . .
H01C H 0.224489 0.151641 0.027242 0.058 Uiso 1 1 calc R U . . .
C28 C 1.0547(2) 0.47497(19) 0.22734(13) 0.0409(5) Uani 1 1 d . . . . .
H011 H 1.118375 0.517464 0.247126 0.049 Uiso 1 1 calc R U . . .
C33 C 0.9713(2) 0.10254(18) -0.13196(13) 0.0386(4) Uani 1 1 d . . . . .
H012 H 1.071828 0.100342 -0.136188 0.046 Uiso 1 1 calc R U . . .
C9 C 0.5487(2) 0.40699(17) 0.33031(13) 0.0391(5) Uani 1 1 d . . . . .
H013 H 0.535842 0.327537 0.362790 0.047 Uiso 1 1 calc R U . . .
C34 C 0.9088(2) 0.06311(18) -0.19587(12) 0.0393(5) Uani 1 1 d . . . . .
H014 H 0.966824 0.036090 -0.243741 0.047 Uiso 1 1 calc R U . . .
C30 C 0.9212(2) 0.3005(2) 0.24915(12) 0.0435(5) Uani 1 1 d . . . . .
H015 H 0.894868 0.226363 0.284332 0.052 Uiso 1 1 calc R U . . .
C35 C 0.7610(2) 0.06420(18) -0.18807(12) 0.0387(4) Uani 1 1 d . . . . .
H016 H 0.719221 0.036881 -0.230677 0.046 Uiso 1 1 calc R U . . .
C27 C 0.9986(2) 0.52248(19) 0.14726(15) 0.0452(5) Uani 1 1 d . . . . .
H017 H 1.023966 0.597440 0.112832 0.054 Uiso 1 1 calc R U . . .
C29 C 1.0162(3) 0.3638(2) 0.27842(14) 0.0512(6) Uani 1 1 d . . . . .
H018 H 1.054259 0.331411 0.332629 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.7590(16) . ?
S1 C1 1.8315(17) . ?
S2 C22 1.7656(17) . ?
S2 C19 1.8385(18) . ?
O2 C11 1.370(2) . ?
O2 C1 1.4379(18) . ?
O1 C2 1.2191(19) . ?
O5 C19 1.430(2) . ?
O5 C23 1.366(2) . ?
O3 C11 1.1978(19) . ?
O4 C20 1.220(2) . ?
O6 C23 1.200(2) . ?
C2 C1 1.564(2) . ?
C2 C3 1.443(2) . ?
C5 C4 1.474(2) . ?
C5 C6 1.391(2) . ?
C5 C10 1.395(2) . ?
C13 C1 1.520(2) . ?
C13 C18 1.390(2) . ?
C13 C14 1.395(2) . ?
C11 C12 1.496(2) . ?
C4 C3 1.355(2) . ?
C3 H00F 0.9300 . ?
C18 H00G 0.9300 . ?
C18 C17 1.390(2) . ?
C25 C22 1.478(2) . ?
C25 C26 1.390(2) . ?
C25 C30 1.389(2) . ?
C21 H00I 0.9300 . ?
C21 C20 1.445(2) . ?
C21 C22 1.352(2) . ?
C31 C19 1.526(2) . ?
C31 C36 1.385(2) . ?
C31 C32 1.391(2) . ?
C20 C19 1.560(2) . ?
C17 H00M 0.9300 . ?
C17 C16 1.383(2) . ?
C16 H00N 0.9300 . ?
C16 C15 1.383(2) . ?
C14 H00O 0.9300 . ?
C14 C15 1.386(2) . ?
C23 C24 1.496(3) . ?
C6 H00R 0.9300 . ?
C6 C7 1.390(3) . ?
C15 H00S 0.9300 . ?
C12 H00A 0.9600 . ?
C12 H00B 0.9600 . ?
C12 H00C 0.9600 . ?
C8 H00U 0.9300 . ?
C8 C7 1.384(3) . ?
C8 C9 1.375(3) . ?
C7 H00V 0.9300 . ?
C36 H00W 0.9300 . ?
C36 C35 1.395(3) . ?
C32 H00X 0.9300 . ?
C32 C33 1.387(3) . ?
C10 H00Y 0.9300 . ?
C10 C9 1.387(3) . ?
C26 H00Z 0.9300 . ?
C26 C27 1.385(3) . ?
C24 H01A 0.9600 . ?
C24 H01B 0.9600 . ?
C24 H01C 0.9600 . ?
C28 H011 0.9300 . ?
C28 C27 1.373(3) . ?
C28 C29 1.382(3) . ?
C33 H012 0.9300 . ?
C33 C34 1.385(3) . ?
C9 H013 0.9300 . ?
C34 H014 0.9300 . ?
C34 C35 1.369(3) . ?
C30 H015 0.9300 . ?
C30 C29 1.385(3) . ?
C35 H016 0.9300 . ?
C27 H017 0.9300 . ?
C29 H018 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
C4 S1 C1 92.43(7) . . ?
C22 S2 C19 91.86(8) . . ?
C11 O2 C1 117.16(12) . . ?
C23 O5 C19 118.58(13) . . ?
O1 C2 C1 120.27(14) . . ?
O1 C2 C3 128.39(14) . . ?
C3 C2 C1 111.31(13) . . ?
C6 C5 C4 120.95(14) . . ?
C6 C5 C10 118.50(15) . . ?
C10 C5 C4 120.52(14) . . ?
C18 C13 C1 120.63(14) . . ?
C18 C13 C14 119.33(15) . . ?
C14 C13 C1 119.87(14) . . ?
O2 C11 C12 110.81(14) . . ?
O3 C11 O2 122.37(14) . . ?
O3 C11 C12 126.82(15) . . ?
C5 C4 S1 117.88(11) . . ?
C3 C4 S1 115.01(12) . . ?
C3 C4 C5 127.08(14) . . ?
O2 C1 S1 111.44(10) . . ?
O2 C1 C2 111.64(12) . . ?
O2 C1 C13 106.96(12) . . ?
C2 C1 S1 105.92(10) . . ?
C13 C1 S1 112.58(10) . . ?
C13 C1 C2 108.32(12) . . ?
C2 C3 H00F 122.7 . . ?
C4 C3 C2 114.63(13) . . ?
C4 C3 H00F 122.7 . . ?
C13 C18 H00G 120.0 . . ?
C17 C18 C13 120.02(15) . . ?
C17 C18 H00G 120.0 . . ?
C26 C25 C22 120.84(15) . . ?
C30 C25 C22 120.91(16) . . ?
C30 C25 C26 118.17(17) . . ?
C20 C21 H00I 122.6 . . ?
C22 C21 H00I 122.6 . . ?
C22 C21 C20 114.71(14) . . ?
C36 C31 C19 120.90(15) . . ?
C36 C31 C32 119.35(16) . . ?
C32 C31 C19 119.74(15) . . ?
O4 C20 C21 128.07(15) . . ?
O4 C20 C19 120.33(14) . . ?
C21 C20 C19 111.33(14) . . ?
C25 C22 S2 118.44(12) . . ?
C21 C22 S2 114.84(13) . . ?
C21 C22 C25 126.60(15) . . ?
C18 C17 H00M 119.8 . . ?
C16 C17 C18 120.35(16) . . ?
C16 C17 H00M 119.8 . . ?
C17 C16 H00N 120.1 . . ?
C15 C16 C17 119.81(16) . . ?
C15 C16 H00N 120.1 . . ?
C13 C14 H00O 119.9 . . ?
C15 C14 C13 120.18(16) . . ?
C15 C14 H00O 119.9 . . ?
O5 C19 S2 111.49(11) . . ?
O5 C19 C31 106.48(13) . . ?
O5 C19 C20 112.76(13) . . ?
C31 C19 S2 111.00(11) . . ?
C31 C19 C20 109.42(13) . . ?
C20 C19 S2 105.74(11) . . ?
O5 C23 C24 110.21(15) . . ?
O6 C23 O5 122.63(16) . . ?
O6 C23 C24 127.16(17) . . ?
C5 C6 H00R 119.8 . . ?
C7 C6 C5 120.38(16) . . ?
C7 C6 H00R 119.8 . . ?
C16 C15 C14 120.30(16) . . ?
C16 C15 H00S 119.8 . . ?
C14 C15 H00S 119.8 . . ?
C11 C12 H00A 109.5 . . ?
C11 C12 H00B 109.5 . . ?
C11 C12 H00C 109.5 . . ?
H00A C12 H00B 109.5 . . ?
H00A C12 H00C 109.5 . . ?
H00B C12 H00C 109.5 . . ?
C7 C8 H00U 120.3 . . ?
C9 C8 H00U 120.3 . . ?
C9 C8 C7 119.50(16) . . ?
C6 C7 H00V 119.8 . . ?
C8 C7 C6 120.48(17) . . ?
C8 C7 H00V 119.8 . . ?
C31 C36 H00W 120.2 . . ?
C31 C36 C35 119.57(17) . . ?
C35 C36 H00W 120.2 . . ?
C31 C32 H00X 119.8 . . ?
C33 C32 C31 120.34(17) . . ?
C33 C32 H00X 119.8 . . ?
C5 C10 H00Y 119.7 . . ?
C9 C10 C5 120.67(17) . . ?
C9 C10 H00Y 119.7 . . ?
C25 C26 H00Z 119.5 . . ?
C27 C26 C25 121.04(18) . . ?
C27 C26 H00Z 119.5 . . ?
C23 C24 H01A 109.5 . . ?
C23 C24 H01B 109.5 . . ?
C23 C24 H01C 109.5 . . ?
H01A C24 H01B 109.5 . . ?
H01A C24 H01C 109.5 . . ?
H01B C24 H01C 109.5 . . ?
C27 C28 H011 120.1 . . ?
C27 C28 C29 119.77(18) . . ?
C29 C28 H011 120.1 . . ?
C32 C33 H012 119.9 . . ?
C34 C33 C32 120.14(18) . . ?
C34 C33 H012 119.9 . . ?
C8 C9 C10 120.46(17) . . ?
C8 C9 H013 119.8 . . ?
C10 C9 H013 119.8 . . ?
C33 C34 H014 120.2 . . ?
C35 C34 C33 119.52(18) . . ?
C35 C34 H014 120.2 . . ?
C25 C30 H015 119.6 . . ?
C29 C30 C25 120.74(19) . . ?
C29 C30 H015 119.6 . . ?
C36 C35 H016 119.5 . . ?
C34 C35 C36 121.05(18) . . ?
C34 C35 H016 119.5 . . ?
C26 C27 H017 120.0 . . ?
C28 C27 C26 120.07(19) . . ?
C28 C27 H017 120.0 . . ?
C28 C29 C30 120.20(19) . . ?
C28 C29 H018 119.9 . . ?
C30 C29 H018 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 -2.84(18) . . . . ?
O1 C2 C1 S1 173.24(12) . . . . ?
O1 C2 C1 O2 51.76(19) . . . . ?
O1 C2 C1 C13 -65.76(18) . . . . ?
O1 C2 C3 C4 -174.48(16) . . . . ?
O4 C20 C19 S2 174.21(13) . . . . ?
O4 C20 C19 O5 52.1(2) . . . . ?
O4 C20 C19 C31 -66.2(2) . . . . ?
C5 C4 C3 C2 175.00(14) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C5 C10 C9 C8 -0.3(3) . . . . ?
C13 C18 C17 C16 0.9(2) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C11 O2 C1 S1 -68.74(14) . . . . ?
C11 O2 C1 C2 49.48(17) . . . . ?
C11 O2 C1 C13 167.81(12) . . . . ?
C4 S1 C1 O2 127.81(11) . . . . ?
C4 S1 C1 C2 6.20(11) . . . . ?
C4 S1 C1 C13 -112.01(11) . . . . ?
C4 C5 C6 C7 -177.19(16) . . . . ?
C4 C5 C10 C9 177.47(17) . . . . ?
C1 S1 C4 C5 179.55(12) . . . . ?
C1 S1 C4 C3 -2.41(13) . . . . ?
C1 O2 C11 O3 -0.3(2) . . . . ?
C1 O2 C11 C12 179.51(13) . . . . ?
C1 C2 C3 C4 7.79(19) . . . . ?
C1 C13 C18 C17 -176.25(14) . . . . ?
C1 C13 C14 C15 175.74(15) . . . . ?
C3 C2 C1 S1 -8.82(15) . . . . ?
C3 C2 C1 O2 -130.29(14) . . . . ?
C3 C2 C1 C13 112.19(14) . . . . ?
C18 C13 C1 S1 -144.91(12) . . . . ?
C18 C13 C1 O2 -22.18(18) . . . . ?
C18 C13 C1 C2 98.30(16) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
C18 C17 C16 C15 -0.1(3) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C25 C30 C29 C28 0.9(4) . . . . ?
C21 C20 C19 S2 -11.25(16) . . . . ?
C21 C20 C19 O5 -133.33(14) . . . . ?
C21 C20 C19 C31 108.37(16) . . . . ?
C31 C36 C35 C34 1.1(3) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C20 C21 C22 S2 3.9(2) . . . . ?
C20 C21 C22 C25 -172.11(15) . . . . ?
C22 S2 C19 O5 134.02(11) . . . . ?
C22 S2 C19 C31 -107.43(12) . . . . ?
C22 S2 C19 C20 11.14(11) . . . . ?
C22 C25 C26 C27 -175.80(18) . . . . ?
C22 C25 C30 C29 175.44(19) . . . . ?
C22 C21 C20 O4 179.30(17) . . . . ?
C22 C21 C20 C19 5.3(2) . . . . ?
C17 C16 C15 C14 -0.5(3) . . . . ?
C14 C13 C1 S1 39.95(17) . . . . ?
C14 C13 C1 O2 162.69(13) . . . . ?
C14 C13 C1 C2 -76.83(17) . . . . ?
C14 C13 C18 C17 -1.1(2) . . . . ?
C19 S2 C22 C25 166.99(13) . . . . ?
C19 S2 C22 C21 -9.35(14) . . . . ?
C19 O5 C23 O6 1.5(2) . . . . ?
C19 O5 C23 C24 -178.92(14) . . . . ?
C19 C31 C36 C35 179.03(15) . . . . ?
C19 C31 C32 C33 -179.70(15) . . . . ?
C23 O5 C19 S2 -73.14(15) . . . . ?
C23 O5 C19 C31 165.64(13) . . . . ?
C23 O5 C19 C20 45.63(19) . . . . ?
C6 C5 C4 S1 -178.52(13) . . . . ?
C6 C5 C4 C3 3.7(3) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C36 C31 C19 S2 -132.55(14) . . . . ?
C36 C31 C19 O5 -11.0(2) . . . . ?
C36 C31 C19 C20 111.13(17) . . . . ?
C36 C31 C32 C33 1.4(3) . . . . ?
C32 C31 C19 S2 48.54(18) . . . . ?
C32 C31 C19 O5 170.07(14) . . . . ?
C32 C31 C19 C20 -67.78(19) . . . . ?
C32 C31 C36 C35 -2.1(3) . . . . ?
C32 C33 C34 C35 -1.4(3) . . . . ?
C10 C5 C4 S1 3.6(2) . . . . ?
C10 C5 C4 C3 -174.21(16) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C26 C25 C22 S2 -10.2(2) . . . . ?
C26 C25 C22 C21 165.64(18) . . . . ?
C26 C25 C30 C29 -1.2(3) . . . . ?
C33 C34 C35 C36 0.7(3) . . . . ?
C9 C8 C7 C6 -0.6(3) . . . . ?
C30 C25 C22 S2 173.20(15) . . . . ?
C30 C25 C22 C21 -10.9(3) . . . . ?
C30 C25 C26 C27 0.9(3) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C29 C28 C27 C26 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
