# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_fs0827
_database_code_depnum_ccdc_archive 'CCDC 1999223'
loop_
_audit_author_name
_audit_author_address
'Wucheng Xie'
;foshan university
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;
_audit_creation_date             2019-08-26
_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         'C23 H18 O3 S'
_chemical_formula_sum            'C23 H18 O3 S'
_chemical_formula_weight         374.43
_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                   8.4310(5)
_cell_length_b                   10.6418(11)
_cell_length_c                   11.6712(14)
_cell_angle_alpha                115.047(11)
_cell_angle_beta                 104.819(8)
_cell_angle_gamma                94.550(7)
_cell_volume                     895.84(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2856
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7830
_cell_measurement_theta_min      3.4990
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.033
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  54.00   1.00    2.50    --  -11.43  57.00 -90.00   88
  2  ω    -85.00  16.00   1.00    2.50    --  -11.43 -57.00 120.00  101
  3  ω    -14.00  76.00   1.00    2.50    --   11.74  77.00  30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0166877000
_diffrn_orient_matrix_UB_12      -0.0461520000
_diffrn_orient_matrix_UB_13      0.0270022000
_diffrn_orient_matrix_UB_21      0.0240094000
_diffrn_orient_matrix_UB_22      0.0588589000
_diffrn_orient_matrix_UB_23      0.0645404000
_diffrn_orient_matrix_UB_31      -0.0841584000
_diffrn_orient_matrix_UB_32      0.0088631000
_diffrn_orient_matrix_UB_33      -0.0109607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2661
_reflns_number_total             3149
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.603
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      1.099
_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)+27.8932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1803
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C9(H9), C18(H18), C2(H2), C7(H7), C12(H12), C22(H22),
 C8(H8), C13(H13), C15(H15), C14(H14), C21(H21), C19(H19)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.01861(16) 0.70288(12) 0.28163(11) 0.0107(3) Uani 1 1 d . . . . .
O3 O 0.3778(5) 1.1123(4) 0.7276(3) 0.0154(10) Uani 1 1 d . . . . .
H3 H 0.298043 1.147160 0.708404 0.023 Uiso 1 1 calc GR . . . .
O1 O -0.1015(5) 0.7794(4) 0.3351(3) 0.0182(10) Uani 1 1 d . . . . .
O2 O 0.0409(5) 0.7024(4) 0.1634(3) 0.0163(10) Uani 1 1 d . . . . .
C17 C -0.0450(6) 0.5260(5) 0.2495(5) 0.0126(13) Uani 1 1 d . . . . .
C10 C 0.6663(7) 1.0068(5) 0.7245(5) 0.0142(13) Uani 1 1 d . . . . .
H10 H 0.669410 1.092129 0.796028 0.017 Uiso 1 1 calc R . . . .
C16 C 0.3574(7) 0.4627(5) 0.3140(5) 0.0159(14) Uani 1 1 d . . . . .
H16 H 0.355724 0.468913 0.395593 0.019 Uiso 1 1 calc R . . . .
C11 C 0.3532(6) 0.5831(5) 0.2937(5) 0.0126(13) Uani 1 1 d . . . . .
C6 C 0.3542(7) 0.7217(5) 0.4061(5) 0.0140(13) Uani 1 1 d . . . . .
C9 C 0.8096(7) 0.9573(5) 0.7206(5) 0.0146(14) Uani 1 1 d . . . . .
H9 H 0.909829 1.009393 0.789031 0.018 Uiso 1 1 calc R . . . .
C18 C -0.1049(6) 0.4966(5) 0.3375(5) 0.0153(14) Uani 1 1 d . . . . .
H18 H -0.100345 0.569863 0.419114 0.018 Uiso 1 1 calc R . . . .
C2 C 0.2182(6) 0.9105(5) 0.5215(5) 0.0134(13) Uani 1 1 d . . . . .
H2 H 0.120169 0.944411 0.523945 0.016 Uiso 1 1 calc R . . . .
C7 C 0.6604(6) 0.7525(5) 0.5117(5) 0.0144(13) Uani 1 1 d . . . . .
H7 H 0.660300 0.668516 0.440072 0.017 Uiso 1 1 calc R . . . .
C12 C 0.3574(6) 0.5722(5) 0.1710(5) 0.0145(13) Uani 1 1 d . . . . .
H12 H 0.358298 0.651504 0.156252 0.017 Uiso 1 1 calc R . . . .
C1 C 0.2147(6) 0.7807(5) 0.4134(4) 0.0109(12) Uani 1 1 d . . . . .
C3 C 0.3650(6) 0.9860(5) 0.6221(5) 0.0122(13) Uani 1 1 d . . . . .
C22 C -0.0496(7) 0.4171(5) 0.1280(5) 0.0145(13) Uani 1 1 d . . . . .
H22 H -0.009360 0.436473 0.068759 0.017 Uiso 1 1 calc R . . . .
C5 C 0.5075(6) 0.8000(5) 0.5129(5) 0.0119(13) Uani 1 1 d . . . . .
C4 C 0.5143(7) 0.9310(5) 0.6222(5) 0.0120(12) Uani 1 1 d . . . . .
C8 C 0.8076(7) 0.8276(5) 0.6135(5) 0.0178(14) Uani 1 1 d . . . . .
H8 H 0.905571 0.793294 0.612074 0.021 Uiso 1 1 calc R . . . .
C20 C -0.1813(7) 0.2477(5) 0.1799(5) 0.0174(14) Uani 1 1 d . . . . .
C13 C 0.3602(7) 0.4421(6) 0.0713(5) 0.0182(15) Uani 1 1 d . . . . .
H13 H 0.359544 0.434122 -0.011347 0.022 Uiso 1 1 calc R . . . .
C15 C 0.3641(8) 0.3350(6) 0.2149(6) 0.0231(16) Uani 1 1 d . . . . .
H15 H 0.368770 0.256109 0.230134 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3638(7) 0.3251(6) 0.0931(5) 0.0206(16) Uani 1 1 d . . . . .
H14 H 0.366152 0.238737 0.025369 0.025 Uiso 1 1 calc R . . . .
C21 C -0.1153(7) 0.2796(6) 0.0971(5) 0.0181(15) Uani 1 1 d . . . . .
H21 H -0.114732 0.205903 0.017404 0.022 Uiso 1 1 calc R . . . .
C19 C -0.1713(7) 0.3578(5) 0.3031(5) 0.0172(14) Uani 1 1 d . . . . .
H19 H -0.209695 0.337616 0.362670 0.021 Uiso 1 1 calc R . . . .
C23 C -0.2594(8) 0.0984(6) 0.1423(6) 0.0274(17) Uani 1 1 d . . . . .
H23A H -0.375325 0.092011 0.137479 0.041 Uiso 1 1 calc GR . . . .
H23B H -0.201227 0.072348 0.208423 0.041 Uiso 1 1 calc GR . . . .
H23C H -0.251492 0.035281 0.057029 0.041 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.449(4) . ?
S1 O2 1.438(4) . ?
S1 C17 1.764(5) . ?
S1 C1 1.785(5) . ?
O3 H3 0.8200 . ?
O3 C3 1.357(5) . ?
C17 C18 1.385(9) . ?
C17 C22 1.389(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.359(8) . ?
C10 C4 1.399(6) . ?
C16 H16 0.9300 . ?
C16 C11 1.401(8) . ?
C16 C15 1.379(7) . ?
C11 C6 1.500(6) . ?
C11 C12 1.396(8) . ?
C6 C1 1.381(8) . ?
C6 C5 1.430(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.412(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.415(6) . ?
C2 C3 1.362(6) . ?
C7 H7 0.9300 . ?
C7 C5 1.423(8) . ?
C7 C8 1.369(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(7) . ?
C3 C4 1.430(8) . ?
C22 H22 0.9300 . ?
C22 C21 1.378(8) . ?
C5 C4 1.421(6) . ?
C8 H8 0.9300 . ?
C20 C21 1.372(9) . ?
C20 C19 1.393(7) . ?
C20 C23 1.499(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(9) . ?
C15 H15 0.9300 . ?
C15 C14 1.381(9) . ?
C14 H14 0.9300 . ?
C21 H21 0.9300 . ?
C19 H19 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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 C17 106.5(3) . . ?
O1 S1 C1 105.6(2) . . ?
O2 S1 O1 118.0(3) . . ?
O2 S1 C17 108.8(2) . . ?
O2 S1 C1 108.9(2) . . ?
C17 S1 C1 108.8(2) . . ?
C3 O3 H3 109.5 . . ?
C18 C17 S1 120.7(4) . . ?
C18 C17 C22 120.6(5) . . ?
C22 C17 S1 118.4(5) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C4 120.8(4) . . ?
C4 C10 H10 119.6 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C11 121.0(6) . . ?
C16 C11 C6 119.4(5) . . ?
C12 C11 C16 118.7(5) . . ?
C12 C11 C6 121.8(5) . . ?
C1 C6 C11 124.0(4) . . ?
C1 C6 C5 116.8(4) . . ?
C5 C6 C11 119.2(5) . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.5(5) . . ?
C19 C18 H18 120.2 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.1(5) . . ?
C5 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C8 C7 C5 121.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(6) . . ?
C13 C12 H12 120.2 . . ?
C6 C1 S1 122.1(3) . . ?
C6 C1 C2 122.9(4) . . ?
C2 C1 S1 114.9(4) . . ?
O3 C3 C2 123.2(5) . . ?
O3 C3 C4 116.6(4) . . ?
C2 C3 C4 120.2(4) . . ?
C17 C22 H22 120.8 . . ?
C21 C22 C17 118.5(6) . . ?
C21 C22 H22 120.8 . . ?
C7 C5 C6 121.4(4) . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 C7 117.3(4) . . ?
C10 C4 C3 121.1(4) . . ?
C10 C4 C5 120.2(5) . . ?
C5 C4 C3 118.6(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.2 . . ?
C21 C20 C19 118.4(5) . . ?
C21 C20 C23 121.7(5) . . ?
C19 C20 C23 119.9(6) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(6) . . ?
C14 C13 H13 119.6 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.5(6) . . ?
C14 C15 H15 120.2 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C22 C21 H21 118.9 . . ?
C20 C21 C22 122.2(5) . . ?
C20 C21 H21 118.9 . . ?
C18 C19 C20 120.6(6) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_fs02
_database_code_depnum_ccdc_archive 'CCDC 1999224'
loop_
_audit_author_name
_audit_author_address
'Wucheng Xie'
;foshan university
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;
_audit_creation_date             2019-09-08
_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 H20 O3 S'
_chemical_formula_sum            'C24 H20 O3 S'
_chemical_formula_weight         388.46
_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                   8.1695(6)
_cell_length_b                   11.1838(9)
_cell_length_c                   12.1869(10)
_cell_angle_alpha                116.288(8)
_cell_angle_beta                 102.125(7)
_cell_angle_gamma                97.876(6)
_cell_volume                     941.83(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2997
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      28.4920
_cell_measurement_theta_min      2.6390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6644
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.957
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    1.50    --   11.74 -57.00   0.00   93
  2  ω    -16.00  10.00   1.00    1.50    --   11.74 -99.00   0.00   26
  3  ω    -13.00  84.00   1.00    1.50    --   11.74  57.00 150.00   97
  4  ω    -13.00  78.00   1.00    1.50    --   11.74  77.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0212453000
_diffrn_orient_matrix_UB_12      -0.0291997000
_diffrn_orient_matrix_UB_13      0.0379799000
_diffrn_orient_matrix_UB_21      -0.0779884000
_diffrn_orient_matrix_UB_22      0.0212445000
_diffrn_orient_matrix_UB_23      -0.0029774000
_diffrn_orient_matrix_UB_31      -0.0440003000
_diffrn_orient_matrix_UB_32      -0.0637972000
_diffrn_orient_matrix_UB_33      -0.0565192000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2770
_reflns_number_total             3321
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.376
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.042
_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)+(0.0555P)²+0.2895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1163
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C16(H16), C18(H18), C2(H2), C22(H22), C12(H12), C14(H14),
 C19(H19), C13(H13), C3(H3), C21(H21), C15(H15)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.98203(7) 0.28958(5) 0.72564(5) 0.01752(17) Uani 1 1 d . . . . .
O1 O 0.61586(18) -0.10402(13) 0.28169(13) 0.0206(4) Uani 1 1 d . . . . .
H1 H 0.704013 -0.129977 0.292796 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.94677(18) 0.30089(14) 0.83996(13) 0.0209(4) Uani 1 1 d . . . . .
O3 O 1.10241(18) 0.20975(14) 0.67990(14) 0.0231(4) Uani 1 1 d . . . . .
C8 C 0.7793(3) 0.0873(2) 0.4897(2) 0.0176(5) Uani 1 1 d . . . . .
H8 H 0.875280 0.051204 0.490016 0.021 Uiso 1 1 calc R . . . .
C7 C 0.6317(3) 0.0177(2) 0.38693(19) 0.0166(5) Uani 1 1 d . . . . .
C5 C 0.3303(3) 0.0031(2) 0.2797(2) 0.0177(5) Uani 1 1 d . . . . .
H5 H 0.325879 -0.079810 0.209782 0.021 Uiso 1 1 calc R . . . .
C9 C 0.7861(3) 0.2135(2) 0.59496(19) 0.0155(4) Uani 1 1 d . . . . .
C4 C 0.1878(3) 0.0553(2) 0.2782(2) 0.0180(5) Uani 1 1 d . . . . .
C6 C 0.4840(3) 0.0727(2) 0.38532(19) 0.0159(4) Uani 1 1 d . . . . .
C1 C 0.4938(3) 0.2006(2) 0.49257(19) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.6565(3) 0.4113(2) 0.7075(2) 0.0174(5) Uani 1 1 d . . . . .
C10 C 0.6485(3) 0.2741(2) 0.6000(2) 0.0168(5) Uani 1 1 d . . . . .
C17 C 1.0663(3) 0.4577(2) 0.7528(2) 0.0176(5) Uani 1 1 d . . . . .
C16 C 0.6744(3) 0.5273(2) 0.6907(2) 0.0214(5) Uani 1 1 d . . . . .
H16 H 0.683303 0.518585 0.612817 0.026 Uiso 1 1 calc R . . . .
C18 C 1.1081(3) 0.5677(2) 0.8753(2) 0.0213(5) Uani 1 1 d . . . . .
H18 H 1.080249 0.555266 0.940412 0.026 Uiso 1 1 calc R . . . .
C2 C 0.3428(3) 0.2505(2) 0.4898(2) 0.0203(5) Uani 1 1 d . . . . .
H2 H 0.343618 0.332483 0.559168 0.024 Uiso 1 1 calc R . . . .
C22 C 1.1024(3) 0.4762(2) 0.6535(2) 0.0222(5) Uani 1 1 d . . . . .
H22 H 1.070968 0.401788 0.570794 0.027 Uiso 1 1 calc R . . . .
C20 C 1.2338(3) 0.7184(2) 0.8033(2) 0.0218(5) Uani 1 1 d . . . . .
C12 C 0.6397(3) 0.4268(2) 0.8248(2) 0.0199(5) Uani 1 1 d . . . . .
H12 H 0.624201 0.350499 0.837566 0.024 Uiso 1 1 calc R . . . .
C14 C 0.6655(3) 0.6694(2) 0.9040(2) 0.0249(5) Uani 1 1 d . . . . .
H14 H 0.669313 0.755387 0.969532 0.030 Uiso 1 1 calc R . . . .
C19 C 1.1924(3) 0.6969(2) 0.8994(2) 0.0232(5) Uani 1 1 d . . . . .
H19 H 1.222135 0.771393 0.981951 0.028 Uiso 1 1 calc R . . . .
C13 C 0.6460(3) 0.5553(2) 0.9218(2) 0.0220(5) Uani 1 1 d . . . . .
H13 H 0.637027 0.564943 0.999988 0.026 Uiso 1 1 calc R . . . .
C3 C 0.1962(3) 0.1794(2) 0.3864(2) 0.0214(5) Uani 1 1 d . . . . .
H3 H 0.099102 0.214127 0.387494 0.026 Uiso 1 1 calc R . . . .
C21 C 1.1850(3) 0.6062(2) 0.6797(2) 0.0243(5) Uani 1 1 d . . . . .
H21 H 1.208647 0.619129 0.613694 0.029 Uiso 1 1 calc R . . . .
C15 C 0.6792(3) 0.6545(2) 0.7874(2) 0.0254(5) Uani 1 1 d . . . . .
H15 H 0.691698 0.730817 0.774497 0.030 Uiso 1 1 calc R . . . .
C23 C 1.3337(3) 0.8584(2) 0.8334(2) 0.0305(6) Uani 1 1 d . . . . .
H23A H 1.331973 0.926864 0.915739 0.046 Uiso 1 1 calc GR . . . .
H23B H 1.281295 0.880084 0.768621 0.046 Uiso 1 1 calc GR . . . .
H23C H 1.451498 0.857478 0.835057 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.0255(3) -0.0141(2) 0.1652(2) 0.0246(5) Uani 1 1 d . . . . .
H24A H 0.005816 0.046522 0.130311 0.037 Uiso 1 1 calc GR . . . .
H24B H -0.071402 -0.034937 0.192512 0.037 Uiso 1 1 calc GR . . . .
H24C H 0.038533 -0.098075 0.100523 0.037 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4361(14) . ?
S1 O3 1.4509(14) . ?
S1 C9 1.783(2) . ?
S1 C17 1.766(2) . ?
O1 H1 0.8200 . ?
O1 C7 1.360(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.368(3) . ?
C8 C9 1.410(3) . ?
C7 C6 1.428(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C5 C6 1.416(3) . ?
C9 C10 1.388(3) . ?
C4 C3 1.409(3) . ?
C4 C24 1.504(3) . ?
C6 C1 1.424(3) . ?
C1 C10 1.433(3) . ?
C1 C2 1.422(3) . ?
C11 C10 1.493(3) . ?
C11 C16 1.394(3) . ?
C11 C12 1.401(3) . ?
C17 C18 1.379(3) . ?
C17 C22 1.395(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.377(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.379(3) . ?
C20 C19 1.391(3) . ?
C20 C21 1.393(3) . ?
C20 C23 1.506(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.380(3) . ?
C14 C15 1.386(3) . ?
C19 H19 0.9300 . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C21 H21 0.9300 . ?
C15 H15 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
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
O2 S1 O3 117.57(9) . . ?
O2 S1 C9 110.22(9) . . ?
O2 S1 C17 108.33(9) . . ?
O3 S1 C9 105.85(9) . . ?
O3 S1 C17 106.97(9) . . ?
C17 S1 C9 107.44(10) . . ?
C7 O1 H1 109.5 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.15(18) . . ?
C9 C8 H8 119.9 . . ?
O1 C7 C8 123.49(17) . . ?
O1 C7 C6 116.23(18) . . ?
C8 C7 C6 120.28(18) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.45(18) . . ?
C6 C5 H5 119.3 . . ?
C8 C9 S1 115.65(15) . . ?
C10 C9 S1 121.38(15) . . ?
C10 C9 C8 122.9(2) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C24 122.41(18) . . ?
C3 C4 C24 119.33(18) . . ?
C5 C6 C7 121.30(18) . . ?
C5 C6 C1 120.03(18) . . ?
C1 C6 C7 118.67(19) . . ?
C6 C1 C10 121.20(18) . . ?
C2 C1 C6 117.3(2) . . ?
C2 C1 C10 121.51(18) . . ?
C16 C11 C10 119.92(18) . . ?
C16 C11 C12 118.17(18) . . ?
C12 C11 C10 121.86(18) . . ?
C9 C10 C1 116.77(17) . . ?
C9 C10 C11 123.68(19) . . ?
C1 C10 C11 119.51(17) . . ?
C18 C17 S1 118.83(16) . . ?
C18 C17 C22 121.09(19) . . ?
C22 C17 S1 119.88(16) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.85(19) . . ?
C3 C2 H2 119.6 . . ?
C17 C22 H22 120.4 . . ?
C21 C22 C17 119.2(2) . . ?
C21 C22 H22 120.4 . . ?
C19 C20 C21 118.3(2) . . ?
C19 C20 C23 120.7(2) . . ?
C21 C20 C23 121.0(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.25(19) . . ?
C13 C12 H12 119.9 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.37(19) . . ?
C15 C14 H14 120.3 . . ?
C18 C19 C20 121.8(2) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 122.09(19) . . ?
C2 C3 H3 119.0 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.697

