# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_19010302
_database_code_depnum_ccdc_archive 'CCDC 2057821'
loop_
_audit_author_name
_audit_author_address
'Chen Junru'
;Sun Yat sen University
China
;
_audit_update_record             
;
2021-01-21 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_audit_creation_date             2019-01-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 O3 S'
_chemical_formula_sum            'C18 H12 O3 S'
_chemical_formula_weight         308.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOS
_chemical_oxdiff_usercomment     Bp-SPhF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.30600(10)
_cell_length_b                   15.1608(2)
_cell_length_c                   22.8838(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2881.66(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4147
_cell_measurement_temperature    294(3)
_cell_measurement_theta_max      72.9660
_cell_measurement_theta_min      6.1510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.195
_diffrn_reflns_theta_min         3.863
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  32.00   1.00    1.00    --  -41.14  57.00   0.00  101
  2  ω     63.00  95.00   1.00    1.00    --   41.14-125.00-150.00   32
  3  ω    101.00 140.00   1.00    2.00    --  106.22 125.00  30.00   39
  4  ω     24.00 107.00   1.00    2.00    --  106.22 -94.00   0.00   83
  5  ω     55.00 177.00   1.00    2.00    --  106.22  15.00 120.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0693078000
_diffrn_orient_matrix_UB_12      -0.0225686000
_diffrn_orient_matrix_UB_13      -0.0606141000
_diffrn_orient_matrix_UB_21      0.1465154000
_diffrn_orient_matrix_UB_22      -0.0439100000
_diffrn_orient_matrix_UB_23      0.0292700000
_diffrn_orient_matrix_UB_31      -0.0902814000
_diffrn_orient_matrix_UB_32      -0.0887880000
_diffrn_orient_matrix_UB_33      0.0009497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2581
_reflns_number_total             2793
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.324
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.084
_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)+(0.0887P)²+0.5771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M)
;
_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
S001 S 0.35676(6) 0.62565(3) 0.32697(2) 0.03579(18) Uani 1 1 d . . . . .
O002 O 0.20434(17) 0.61070(9) 0.35511(6) 0.0440(3) Uani 1 1 d . . . . .
O003 O 0.61894(18) 0.60808(11) 0.52846(6) 0.0499(4) Uani 1 1 d . . . . .
O004 O 0.3907(2) 0.58044(10) 0.27324(6) 0.0536(4) Uani 1 1 d . . . . .
C005 C 0.5001(2) 0.61045(10) 0.43770(8) 0.0334(4) Uani 1 1 d . . . . .
C006 C 0.3782(2) 0.73986(12) 0.31430(7) 0.0338(4) Uani 1 1 d . . . . .
C007 C 0.3138(2) 0.79925(12) 0.35413(7) 0.0356(4) Uani 1 1 d . . . . .
H007 H 0.2571 0.7791 0.3865 0.043 Uiso 1 1 calc R . . . .
C008 C 0.3784(2) 0.63296(11) 0.48125(8) 0.0348(4) Uani 1 1 d . . . . .
C009 C 0.2148(2) 0.65441(12) 0.48223(8) 0.0392(4) Uani 1 1 d . . . . .
H009 H 0.1554 0.6556 0.4478 0.047 Uiso 1 1 calc R . . . .
C00A C 0.4593(3) 0.63112(12) 0.53483(8) 0.0424(4) Uani 1 1 d . . . . .
C00B C 0.5143(2) 0.60200(11) 0.37645(8) 0.0361(4) Uani 1 1 d . . . . .
C00C C 0.6419(2) 0.59606(13) 0.46963(9) 0.0410(4) Uani 1 1 d . . . . .
C00D C 0.4648(3) 0.76885(14) 0.26608(8) 0.0473(5) Uani 1 1 d . . . . .
H00D H 0.5084 0.7287 0.2397 0.057 Uiso 1 1 calc R . . . .
C00E C 0.4197(3) 0.91813(13) 0.29700(8) 0.0448(4) Uani 1 1 d . . . . .
H00E H 0.4329 0.9783 0.2908 0.054 Uiso 1 1 calc R . . . .
C00F C 0.3352(3) 0.88911(13) 0.34502(9) 0.0417(4) Uani 1 1 d . . . . .
H00F H 0.2924 0.9296 0.3713 0.050 Uiso 1 1 calc R . . . .
C00G C 0.6619(3) 0.58076(15) 0.35161(10) 0.0489(5) Uani 1 1 d . . . . .
H00G H 0.6704 0.5760 0.3112 0.059 Uiso 1 1 calc R . . . .
C00H C 0.7891(2) 0.57415(15) 0.44590(11) 0.0533(5) Uani 1 1 d . . . . .
H00H H 0.8791 0.5649 0.4693 0.064 Uiso 1 1 calc R . . . .
C00I C 0.1422(3) 0.67377(14) 0.53503(9) 0.0488(5) Uani 1 1 d . . . . .
H00I H 0.0334 0.6880 0.5357 0.059 Uiso 1 1 calc R . . . .
C00J C 0.3890(3) 0.65055(18) 0.58788(9) 0.0570(6) Uani 1 1 d . . . . .
H00J H 0.4476 0.6490 0.6225 0.068 Uiso 1 1 calc R . . . .
C00K C 0.4851(3) 0.85875(15) 0.25797(9) 0.0519(5) Uani 1 1 d . . . . .
H00K H 0.5432 0.8792 0.2260 0.062 Uiso 1 1 calc R . . . .
C00L C 0.7968(3) 0.56652(16) 0.38608(12) 0.0578(6) Uani 1 1 d . . . . .
H00L H 0.8940 0.5516 0.3685 0.069 Uiso 1 1 calc R . . . .
C00M C 0.2285(3) 0.67239(16) 0.58716(9) 0.0573(6) Uani 1 1 d . . . . .
H00M H 0.1768 0.6864 0.6220 0.069 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O002 1.4384(15) . ?
S001 O004 1.4356(13) . ?
S001 C006 1.7645(18) . ?
S001 C00B 1.7672(19) . ?
O003 C00A 1.379(3) . ?
O003 C00C 1.372(3) . ?
C005 C008 1.460(2) . ?
C005 C00B 1.412(3) . ?
C005 C00C 1.403(3) . ?
C006 C007 1.388(2) . ?
C006 C00D 1.389(3) . ?
C007 H007 0.9300 . ?
C007 C00F 1.390(3) . ?
C008 C009 1.398(3) . ?
C008 C00A 1.398(3) . ?
C009 H009 0.9300 . ?
C009 C00I 1.382(3) . ?
C00A C00J 1.379(3) . ?
C00B C00G 1.389(3) . ?
C00C C00H 1.378(3) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.386(3) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.376(3) . ?
C00E C00K 1.380(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00L 1.387(3) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.375(4) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.392(3) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.374(4) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 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
O002 S001 C006 108.48(8) . . ?
O002 S001 C00B 109.44(9) . . ?
O004 S001 O002 118.76(9) . . ?
O004 S001 C006 107.94(9) . . ?
O004 S001 C00B 107.84(9) . . ?
C006 S001 C00B 103.28(8) . . ?
C00C O003 C00A 105.72(15) . . ?
C00B C005 C008 139.17(17) . . ?
C00C C005 C008 105.19(16) . . ?
C00C C005 C00B 115.62(17) . . ?
C007 C006 S001 119.33(13) . . ?
C007 C006 C00D 121.05(17) . . ?
C00D C006 S001 119.56(14) . . ?
C006 C007 H007 120.4 . . ?
C006 C007 C00F 119.22(17) . . ?
C00F C007 H007 120.4 . . ?
C009 C008 C005 137.60(17) . . ?
C009 C008 C00A 117.25(18) . . ?
C00A C008 C005 105.15(16) . . ?
C008 C009 H009 120.4 . . ?
C00I C009 C008 119.17(18) . . ?
C00I C009 H009 120.4 . . ?
O003 C00A C008 111.98(17) . . ?
C00J C00A O003 123.65(19) . . ?
C00J C00A C008 124.4(2) . . ?
C005 C00B S001 123.75(14) . . ?
C00G C00B S001 115.99(15) . . ?
C00G C00B C005 120.06(18) . . ?
O003 C00C C005 111.95(17) . . ?
O003 C00C C00H 122.81(19) . . ?
C00H C00C C005 125.2(2) . . ?
C006 C00D H00D 120.6 . . ?
C00K C00D C006 118.74(18) . . ?
C00K C00D H00D 120.6 . . ?
C00F C00E H00E 119.7 . . ?
C00F C00E C00K 120.60(19) . . ?
C00K C00E H00E 119.7 . . ?
C007 C00F H00F 120.1 . . ?
C00E C00F C007 119.90(18) . . ?
C00E C00F H00F 120.1 . . ?
C00B C00G H00G 119.5 . . ?
C00L C00G C00B 121.1(2) . . ?
C00L C00G H00G 119.5 . . ?
C00C C00H H00H 121.5 . . ?
C00L C00H C00C 116.99(19) . . ?
C00L C00H H00H 121.5 . . ?
C009 C00I H00I 119.3 . . ?
C009 C00I C00M 121.5(2) . . ?
C00M C00I H00I 119.3 . . ?
C00A C00J H00J 121.6 . . ?
C00M C00J C00A 116.8(2) . . ?
C00M C00J H00J 121.6 . . ?
C00D C00K H00K 119.8 . . ?
C00E C00K C00D 120.48(18) . . ?
C00E C00K H00K 119.8 . . ?
C00G C00L H00L 119.5 . . ?
C00H C00L C00G 121.00(19) . . ?
C00H C00L H00L 119.5 . . ?
C00I C00M H00M 119.6 . . ?
C00J C00M C00I 120.90(19) . . ?
C00J C00M H00M 119.6 . . ?

_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 1.585
_oxdiff_exptl_absorpt_empirical_full_min 0.694
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2057825'
loop_
_audit_author_name
_audit_author_address
'Chen Junru'
;Sun Yat sen University
China
;
_audit_update_record             
;
2021-01-21 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_audit_creation_date             2018-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 O3 S'
_chemical_formula_sum            'C18 H12 O3 S'
_chemical_formula_weight         308.34
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z'

_cell_length_a                   11.440(2)
_cell_length_b                   7.6431(14)
_cell_length_c                   16.451(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.999(6)
_cell_angle_gamma                90.00
_cell_volume                     1430.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      62.4080
_cell_measurement_theta_min      4.4200
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13177
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1459
_reflns_number_total             3272
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1672
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1469
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C33(H33), C30(H30), C29(H29), C24(H24), C23(H23), C27(H27), C36(H36),
 C37(H37), C38(H38), C25(H25), C39(H39), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.16464(9) 0.64456(13) 0.17800(5) 0.0700(3) Uani 1 d . . .
O3 O 0.2349(2) 0.5326(3) 0.48864(14) 0.0717(7) Uani 1 d . . .
C32 C 0.1727(3) 0.6003(4) 0.41921(19) 0.0581(8) Uani 1 d . . .
C31 C 0.0779(3) 0.7003(4) 0.43861(19) 0.0572(8) Uani 1 d . . .
C33 C 0.2013(3) 0.5759(4) 0.3405(2) 0.0609(9) Uani 1 d . . .
H33 H 0.2641 0.5060 0.3291 0.073 Uiso 1 calc . . R
C28 C 0.1313(3) 0.6616(4) 0.28011(18) 0.0570(8) Uani 1 d . . .
C22 C 0.0612(3) 0.4935(4) 0.13367(17) 0.0572(8) Uani 1 d . . .
C34 C 0.0805(3) 0.6945(4) 0.5268(2) 0.0594(9) Uani 1 d . . .
O1 O 0.2796(2) 0.5682(4) 0.17904(14) 0.0888(8) Uani 1 d . . .
C30 C 0.0075(3) 0.7794(4) 0.3765(2) 0.0674(9) Uani 1 d . . .
H30 H -0.0578 0.8440 0.3877 0.081 Uiso 1 calc . . R
O2 O 0.1407(3) 0.8120(3) 0.13967(14) 0.0914(9) Uani 1 d . . .
C29 C 0.0349(3) 0.7617(4) 0.2970(2) 0.0663(9) Uani 1 d . . .
H29 H -0.0111 0.8169 0.2546 0.080 Uiso 1 calc . . R
C24 C -0.1302(4) 0.4300(6) 0.0706(2) 0.0814(11) Uani 1 d . . .
H24 H -0.2051 0.4666 0.0502 0.098 Uiso 1 calc . . R
C23 C -0.0486(4) 0.5499(5) 0.10268(19) 0.0685(10) Uani 1 d . . .
H23 H -0.0674 0.6682 0.1034 0.082 Uiso 1 calc . . R
C35 C 0.1758(3) 0.5938(4) 0.5536(2) 0.0646(9) Uani 1 d . . .
C27 C 0.0908(4) 0.3188(5) 0.1331(2) 0.0740(10) Uani 1 d . . .
H27 H 0.1651 0.2812 0.1544 0.089 Uiso 1 calc . . R
C36 C 0.2103(4) 0.5578(5) 0.6347(2) 0.0797(11) Uani 1 d . . .
H36 H 0.2757 0.4894 0.6512 0.096 Uiso 1 calc . . R
C37 C 0.1411(4) 0.6304(5) 0.6897(2) 0.0845(12) Uani 1 d . . .
H37 H 0.1605 0.6106 0.7452 0.101 Uiso 1 calc . . R
C38 C 0.0446(4) 0.7308(5) 0.6652(2) 0.0830(12) Uani 1 d . . .
H38 H 0.0004 0.7770 0.7044 0.100 Uiso 1 calc . . R
C25 C -0.1011(5) 0.2571(6) 0.0689(2) 0.0870(13) Uani 1 d . . .
H25 H -0.1562 0.1767 0.0462 0.104 Uiso 1 calc . . R
C39 C 0.0117(3) 0.7649(4) 0.5838(2) 0.0735(10) Uani 1 d . . .
H39 H -0.0542 0.8325 0.5675 0.088 Uiso 1 calc . . R
C26 C 0.0072(5) 0.2004(5) 0.0998(2) 0.0870(13) Uani 1 d . . .
H26 H 0.0252 0.0819 0.0986 0.104 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C28 1.766(3) . ?
S1 C22 1.756(3) . ?
S1 O1 1.437(3) . ?
S1 O2 1.440(2) . ?
O3 C32 1.382(3) . ?
O3 C35 1.403(4) . ?
C32 C31 1.390(4) . ?
C32 C33 1.381(4) . ?
C31 C34 1.448(4) . ?
C31 C30 1.374(4) . ?
C33 H33 0.9300 . ?
C33 C28 1.375(4) . ?
C28 C29 1.394(4) . ?
C22 C23 1.375(5) . ?
C22 C27 1.378(4) . ?
C34 C35 1.369(5) . ?
C34 C39 1.395(4) . ?
C30 H30 0.9300 . ?
C30 C29 1.384(4) . ?
C29 H29 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.374(5) . ?
C24 C25 1.364(5) . ?
C23 H23 0.9300 . ?
C35 C36 1.380(4) . ?
C27 H27 0.9300 . ?
C27 C26 1.387(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.379(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.369(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.377(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.360(5) . ?
C39 H39 0.9300 . ?
C26 H26 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
C22 S1 C28 103.91(14) . . ?
O1 S1 C28 107.87(16) . . ?
O1 S1 C22 108.30(17) . . ?
O1 S1 O2 119.88(18) . . ?
O2 S1 C28 107.51(16) . . ?
O2 S1 C22 108.24(17) . . ?
C32 O3 C35 104.9(3) . . ?
O3 C32 C31 111.3(3) . . ?
C33 C32 O3 124.9(3) . . ?
C33 C32 C31 123.8(3) . . ?
C32 C31 C34 106.2(3) . . ?
C30 C31 C32 118.8(3) . . ?
C30 C31 C34 135.0(3) . . ?
C32 C33 H33 122.1 . . ?
C28 C33 C32 115.9(3) . . ?
C28 C33 H33 122.1 . . ?
C33 C28 S1 119.0(3) . . ?
C33 C28 C29 122.1(3) . . ?
C29 C28 S1 118.9(3) . . ?
C23 C22 S1 119.8(3) . . ?
C23 C22 C27 121.1(3) . . ?
C27 C22 S1 119.0(3) . . ?
C35 C34 C31 105.8(3) . . ?
C35 C34 C39 119.1(3) . . ?
C39 C34 C31 135.1(4) . . ?
C31 C30 H30 120.4 . . ?
C31 C30 C29 119.2(3) . . ?
C29 C30 H30 120.4 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.9 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C25 C24 C23 119.8(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C34 C35 O3 111.9(3) . . ?
C34 C35 C36 124.1(3) . . ?
C36 C35 O3 123.9(3) . . ?
C22 C27 H27 120.8 . . ?
C22 C27 C26 118.4(4) . . ?
C26 C27 H27 120.8 . . ?
C35 C36 H36 122.3 . . ?
C37 C36 C35 115.4(4) . . ?
C37 C36 H36 122.3 . . ?
C36 C37 H37 118.9 . . ?
C38 C37 C36 122.2(4) . . ?
C38 C37 H37 118.9 . . ?
C37 C38 H38 119.3 . . ?
C37 C38 C39 121.5(4) . . ?
C39 C38 H38 119.3 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25 119.5 . . ?
C34 C39 H39 121.1 . . ?
C38 C39 C34 117.7(4) . . ?
C38 C39 H39 121.1 . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.2(4) . . ?
C25 C26 H26 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 C28 C29 C30 -179.2(3) . . . . ?
S1 C22 C23 C24 -177.8(2) . . . . ?
S1 C22 C27 C26 178.3(2) . . . . ?
O3 C32 C31 C34 -0.2(4) . . . . ?
O3 C32 C31 C30 179.2(3) . . . . ?
O3 C32 C33 C28 -176.9(3) . . . . ?
O3 C35 C36 C37 179.8(3) . . . . ?
C32 O3 C35 C34 0.4(3) . . . . ?
C32 O3 C35 C36 -179.2(3) . . . . ?
C32 C31 C34 C35 0.4(4) . . . . ?
C32 C31 C34 C39 -179.7(4) . . . . ?
C32 C31 C30 C29 -1.9(5) . . . . ?
C32 C33 C28 S1 177.7(2) . . . . ?
C32 C33 C28 C29 -2.2(5) . . . . ?
C31 C32 C33 C28 1.7(5) . . . . ?
C31 C34 C35 O3 -0.5(4) . . . . ?
C31 C34 C35 C36 179.1(3) . . . . ?
C31 C34 C39 C38 -179.0(3) . . . . ?
C31 C30 C29 C28 1.4(5) . . . . ?
C33 C32 C31 C34 -179.0(3) . . . . ?
C33 C32 C31 C30 0.4(5) . . . . ?
C33 C28 C29 C30 0.7(5) . . . . ?
C28 S1 C22 C23 85.3(3) . . . . ?
C28 S1 C22 C27 -92.7(3) . . . . ?
C22 S1 C28 C33 102.7(3) . . . . ?
C22 S1 C28 C29 -77.4(3) . . . . ?
C22 C27 C26 C25 -0.1(5) . . . . ?
C34 C31 C30 C29 177.2(3) . . . . ?
C34 C35 C36 C37 0.3(5) . . . . ?
O1 S1 C28 C33 -12.1(3) . . . . ?
O1 S1 C28 C29 167.8(3) . . . . ?
O1 S1 C22 C23 -160.2(2) . . . . ?
O1 S1 C22 C27 21.8(3) . . . . ?
C30 C31 C34 C35 -178.8(4) . . . . ?
C30 C31 C34 C39 1.1(6) . . . . ?
O2 S1 C28 C33 -142.7(3) . . . . ?
O2 S1 C28 C29 37.2(3) . . . . ?
O2 S1 C22 C23 -28.8(3) . . . . ?
O2 S1 C22 C27 153.2(3) . . . . ?
C24 C25 C26 C27 -0.7(6) . . . . ?
C23 C22 C27 C26 0.4(5) . . . . ?
C23 C24 C25 C26 1.2(6) . . . . ?
C35 O3 C32 C31 -0.1(3) . . . . ?
C35 O3 C32 C33 178.7(3) . . . . ?
C35 C34 C39 C38 0.8(5) . . . . ?
C35 C36 C37 C38 0.2(6) . . . . ?
C27 C22 C23 C24 0.1(5) . . . . ?
C36 C37 C38 C39 -0.1(6) . . . . ?
C37 C38 C39 C34 -0.4(5) . . . . ?
C25 C24 C23 C22 -0.9(5) . . . . ?
C39 C34 C35 O3 179.6(3) . . . . ?
C39 C34 C35 C36 -0.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
