# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_cmrv_ih_361_autored
_database_code_depnum_ccdc_archive 'CCDC 2245728'
loop_
_audit_author_name
_audit_author_address
'Darshan Matre'
;IIT BOMBAY
India
;
_audit_update_record             
;
2023-03-02 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2021-10-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 O4 S'
_chemical_formula_sum            'C22 H26 O4 S'
_chemical_formula_weight         386.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOS
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                   19.4337(5)
_cell_length_b                   6.53480(10)
_cell_length_c                   17.2542(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.748(4)
_cell_angle_gamma                90
_cell_volume                     1989.96(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8681
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1100
_cell_measurement_theta_min      2.3990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23710
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.362
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -94.86 139.14   1.00    3.00   4.82 -11.63 -31.50    --   234
  2  φ    -38.27 209.73   1.00    3.00  79.23 -11.63  31.50    --   248
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0311708000
_diffrn_orient_matrix_UB_12      0.0671075000
_diffrn_orient_matrix_UB_13      0.0094565000
_diffrn_orient_matrix_UB_21      -0.0066254000
_diffrn_orient_matrix_UB_22      0.0004568000
_diffrn_orient_matrix_UB_23      -0.0436548000
_diffrn_orient_matrix_UB_31      -0.0245004000
_diffrn_orient_matrix_UB_32      0.0853274000
_diffrn_orient_matrix_UB_33      -0.0072293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3083
_reflns_number_total             3477
_reflns_odcompleteness_completeness 87.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     34.21
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.360
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.074
_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)+(0.0582P)²+0.8896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 0.80277(2) 0.39978(6) 0.49286(3) 0.02156(17) Uani 1 1 d . . . . .
O1 O 0.60464(7) 0.63935(19) 0.33068(8) 0.0264(3) Uani 1 1 d . . . . .
O2 O 0.79534(7) 0.22241(19) 0.53828(9) 0.0299(3) Uani 1 1 d . . . . .
O3 O 0.81783(7) 0.3647(2) 0.41903(9) 0.0323(3) Uani 1 1 d . . . . .
O4 O 0.43736(7) 0.8069(2) 0.47285(10) 0.0356(4) Uani 1 1 d . . . . .
C1 C 0.87597(9) 0.5606(3) 0.56535(12) 0.0208(4) Uani 1 1 d . . . . .
H1 H 0.858533 0.614118 0.608425 0.025 Uiso 1 1 calc R . . . .
C2 C 0.94783(10) 0.4350(3) 0.61282(14) 0.0311(5) Uani 1 1 d . . . . .
H2A H 0.936645 0.318141 0.642241 0.037 Uiso 1 1 calc R . . . .
H2B H 0.966825 0.380303 0.571915 0.037 Uiso 1 1 calc R . . . .
C3 C 1.00752(12) 0.5729(4) 0.67781(16) 0.0426(6) Uani 1 1 d . . . . .
H3A H 0.989221 0.620328 0.720359 0.051 Uiso 1 1 calc R . . . .
H3B H 1.054644 0.493714 0.708317 0.051 Uiso 1 1 calc R . . . .
C4 C 1.02464(12) 0.7579(4) 0.63489(17) 0.0466(6) Uani 1 1 d . . . . .
H4A H 1.061608 0.847717 0.678864 0.056 Uiso 1 1 calc R . . . .
H4B H 1.047579 0.711386 0.596392 0.056 Uiso 1 1 calc R . . . .
C5 C 0.95270(12) 0.8778(3) 0.58396(16) 0.0393(5) Uani 1 1 d . . . . .
H5A H 0.964622 0.990539 0.553221 0.047 Uiso 1 1 calc R . . . .
H5B H 0.933724 0.939470 0.623700 0.047 Uiso 1 1 calc R . . . .
C6 C 0.89073(11) 0.7433(3) 0.51960(13) 0.0302(5) Uani 1 1 d . . . . .
H6A H 0.843620 0.823936 0.491191 0.036 Uiso 1 1 calc R . . . .
H6B H 0.906756 0.694899 0.475317 0.036 Uiso 1 1 calc R . . . .
C7 C 0.71800(9) 0.5501(3) 0.45558(11) 0.0206(4) Uani 1 1 d . . . . .
C8 C 0.67987(10) 0.5644(3) 0.35994(12) 0.0238(4) Uani 1 1 d . . . . .
H8A H 0.709515 0.656586 0.339938 0.029 Uiso 1 1 calc R . . . .
H8B H 0.678975 0.427296 0.335169 0.029 Uiso 1 1 calc R . . . .
C9 C 0.59967(10) 0.8269(3) 0.37302(12) 0.0247(4) Uani 1 1 d . . . . .
C10 C 0.62132(9) 0.7822(3) 0.46723(12) 0.0219(4) Uani 1 1 d . . . . .
H10 H 0.633426 0.915815 0.498314 0.026 Uiso 1 1 calc R . . . .
C11 C 0.69186(9) 0.6471(3) 0.50622(11) 0.0197(4) Uani 1 1 d . . . . .
C12 C 0.51806(11) 0.8920(3) 0.32558(14) 0.0331(5) Uani 1 1 d . . . . .
H12 H 0.502294 0.940576 0.268818 0.040 Uiso 1 1 calc R . . . .
C13 C 0.55675(10) 0.6821(3) 0.48316(13) 0.0268(4) Uani 1 1 d . . . . .
H13A H 0.549502 0.539966 0.461271 0.032 Uiso 1 1 calc R . . . .
H13B H 0.571299 0.675913 0.545390 0.032 Uiso 1 1 calc R . . . .
C14 C 0.48268(10) 0.7972(3) 0.44071(13) 0.0283(4) Uani 1 1 d . . . . .
C15 C 0.46695(11) 0.8860(3) 0.35759(14) 0.0354(5) Uani 1 1 d . . . . .
H15 H 0.418125 0.941842 0.325075 0.042 Uiso 1 1 calc R . . . .
C16 C 0.64921(11) 0.9957(3) 0.36274(14) 0.0337(5) Uani 1 1 d . . . . .
H16A H 0.702573 0.965213 0.398522 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.635681 1.126808 0.380226 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.641250 1.003762 0.302862 0.051 Uiso 1 1 calc GR . . . .
C17 C 0.72617(9) 0.6336(3) 0.60100(12) 0.0214(4) Uani 1 1 d . . . . .
C18 C 0.75801(10) 0.8079(3) 0.65020(13) 0.0271(4) Uani 1 1 d . . . . .
H18 H 0.755475 0.936021 0.623143 0.032 Uiso 1 1 calc R . . . .
C19 C 0.79309(11) 0.7934(4) 0.73811(13) 0.0346(5) Uani 1 1 d . . . . .
H19 H 0.815162 0.911539 0.771303 0.041 Uiso 1 1 calc R . . . .
C20 C 0.79630(12) 0.6073(4) 0.77822(14) 0.0389(6) Uani 1 1 d . . . . .
H20 H 0.821775 0.597056 0.838583 0.047 Uiso 1 1 calc R . . . .
C21 C 0.76224(11) 0.4368(3) 0.72993(13) 0.0347(5) Uani 1 1 d . . . . .
H21 H 0.762967 0.310369 0.757412 0.042 Uiso 1 1 calc R . . . .
C22 C 0.72723(10) 0.4492(3) 0.64212(12) 0.0261(4) Uani 1 1 d . . . . .
H22 H 0.703718 0.331423 0.609482 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4399(14) . ?
S1 O3 1.4398(14) . ?
S1 C1 1.7898(17) . ?
S1 C7 1.7905(17) . ?
O1 C8 1.419(2) . ?
O1 C9 1.451(2) . ?
O4 C14 1.223(2) . ?
C1 C2 1.529(2) . ?
C1 C6 1.523(3) . ?
C2 C3 1.525(3) . ?
C3 C4 1.525(3) . ?
C4 C5 1.521(3) . ?
C5 C6 1.529(3) . ?
C7 C8 1.502(3) . ?
C7 C11 1.340(2) . ?
C9 C10 1.527(3) . ?
C9 C12 1.510(3) . ?
C9 C16 1.522(3) . ?
C10 C11 1.529(2) . ?
C10 C13 1.539(2) . ?
C11 C17 1.488(3) . ?
C12 C15 1.324(3) . ?
C13 C14 1.514(2) . ?
C14 C15 1.456(3) . ?
C17 C18 1.400(3) . ?
C17 C22 1.394(3) . ?
C18 C19 1.382(3) . ?
C19 C20 1.388(3) . ?
C20 C21 1.383(3) . ?
C21 C22 1.379(3) . ?

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 C1 108.89(8) . . ?
O2 S1 C7 110.52(8) . . ?
O3 S1 O2 117.22(8) . . ?
O3 S1 C1 108.38(8) . . ?
O3 S1 C7 105.47(8) . . ?
C1 S1 C7 105.74(8) . . ?
C8 O1 C9 112.84(13) . . ?
C2 C1 S1 109.83(12) . . ?
C6 C1 S1 111.42(13) . . ?
C6 C1 C2 111.75(15) . . ?
C3 C2 C1 108.62(16) . . ?
C4 C3 C2 111.40(19) . . ?
C5 C4 C3 110.76(17) . . ?
C4 C5 C6 112.18(17) . . ?
C1 C6 C5 109.64(17) . . ?
C8 C7 S1 112.66(13) . . ?
C11 C7 S1 124.63(14) . . ?
C11 C7 C8 122.66(16) . . ?
O1 C8 C7 111.92(15) . . ?
O1 C9 C10 109.11(14) . . ?
O1 C9 C12 103.96(15) . . ?
O1 C9 C16 112.02(15) . . ?
C12 C9 C10 112.94(16) . . ?
C12 C9 C16 107.75(16) . . ?
C16 C9 C10 110.91(16) . . ?
C9 C10 C11 112.06(15) . . ?
C9 C10 C13 112.94(15) . . ?
C11 C10 C13 108.89(14) . . ?
C7 C11 C10 120.05(16) . . ?
C7 C11 C17 124.83(16) . . ?
C17 C11 C10 115.12(14) . . ?
C15 C12 C9 124.53(19) . . ?
C14 C13 C10 112.55(15) . . ?
O4 C14 C13 121.71(18) . . ?
O4 C14 C15 122.13(18) . . ?
C15 C14 C13 116.09(17) . . ?
C12 C15 C14 122.54(18) . . ?
C18 C17 C11 119.95(17) . . ?
C22 C17 C11 120.99(16) . . ?
C22 C17 C18 119.06(17) . . ?
C19 C18 C17 119.98(19) . . ?
C18 C19 C20 120.4(2) . . ?
C21 C20 C19 119.7(2) . . ?
C22 C21 C20 120.4(2) . . ?
C21 C22 C17 120.33(19) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.621
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_cmrv_1h_468_b_autored
_database_code_depnum_ccdc_archive 'CCDC 2250720'
loop_
_audit_author_name
_audit_author_address
'Akshay Nair'
;IIT Bombay
India
;
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2023-03-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 O4 S'
_chemical_formula_sum            'C22 H28 O4 S'
_chemical_formula_weight         388.50
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H28 O4 S1'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5572(2)
_cell_length_b                   12.2026(2)
_cell_length_c                   15.4049(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1984.54(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16338
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      32.8320
_cell_measurement_theta_min      2.1150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.089
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1701
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31354
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.129
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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  φ    154.25 334.25   1.00    1.00 -25.75   0.00  73.76    --   180
  2  φ    -76.21  60.79   0.50    3.00  15.81  -9.84 -59.25    --   274
  3  φ    157.44 301.44   0.50    3.00  81.02  -9.84  31.50    --   288
  4  ω   -100.81  15.69   0.50    3.00    --   -9.84 -59.25  20.08  233
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0010089000
_diffrn_orient_matrix_UB_12      -0.0219043000
_diffrn_orient_matrix_UB_13      0.0426489000
_diffrn_orient_matrix_UB_21      -0.0388140000
_diffrn_orient_matrix_UB_22      0.0437245000
_diffrn_orient_matrix_UB_23      0.0145345000
_diffrn_orient_matrix_UB_31      -0.0548339000
_diffrn_orient_matrix_UB_32      -0.0313868000
_diffrn_orient_matrix_UB_33      -0.0095388000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3295
_reflns_number_total             3508
_reflns_odcompleteness_completeness 90.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.56
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.284
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 1319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.115
_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)+(0.0393P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C20(H20), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C19(H19A,H19B), C3(H3A,H3B), C4(H4A,H4B), C17(H17A,H17B), C5(H5A,
 H5B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C22(H22), C10(H10), C21(H21), C11(H11), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 0.36580(5) 0.49218(5) 0.55914(3) 0.01988(18) Uani 1 1 d . . . . .
O3 O 0.69442(15) 0.48617(13) 0.43068(10) 0.0214(4) Uani 1 1 d . . . . .
O4 O 0.74853(19) 0.81383(14) 0.24315(11) 0.0298(5) Uani 1 1 d . . . . .
H4 H 0.792100 0.826046 0.287740 0.045 Uiso 1 1 calc GR . . . .
O1 O 0.40358(17) 0.39229(15) 0.60218(12) 0.0298(5) Uani 1 1 d . . . . .
O2 O 0.36799(18) 0.59193(14) 0.60999(11) 0.0311(4) Uani 1 1 d . . . . .
C8 C 0.4545(2) 0.56984(18) 0.40095(15) 0.0175(5) Uani 1 1 d . . . . .
C1 C 0.1972(2) 0.3711(2) 0.46321(16) 0.0234(6) Uani 1 1 d . . . . .
H1A H 0.219283 0.306366 0.498866 0.028 Uiso 1 1 calc R . . . .
H1B H 0.256703 0.374631 0.413623 0.028 Uiso 1 1 calc R . . . .
C15 C 0.5534(2) 0.57761(19) 0.33018(15) 0.0178(5) Uani 1 1 d . . . . .
H15 H 0.509804 0.563795 0.273593 0.021 Uiso 1 1 calc R . . . .
C7 C 0.4741(2) 0.50830(19) 0.47136(14) 0.0177(5) Uani 1 1 d . . . . .
C14 C 0.3155(3) 0.7302(2) 0.43547(16) 0.0258(6) Uani 1 1 d . . . . .
H14 H 0.372855 0.751086 0.480009 0.031 Uiso 1 1 calc R . . . .
C19 C 0.6082(2) 0.69477(19) 0.32690(15) 0.0200(5) Uani 1 1 d . . . . .
H19A H 0.538152 0.748554 0.323322 0.024 Uiso 1 1 calc R . . . .
H19B H 0.656703 0.709621 0.380617 0.024 Uiso 1 1 calc R . . . .
C22 C 0.7775(2) 0.5240(2) 0.29248(15) 0.0257(6) Uani 1 1 d . . . . .
H22 H 0.846689 0.474221 0.293220 0.031 Uiso 1 1 calc R . . . .
C9 C 0.3394(2) 0.63722(19) 0.38540(15) 0.0181(5) Uani 1 1 d . . . . .
C16 C 0.6583(2) 0.4916(2) 0.33966(14) 0.0203(5) Uani 1 1 d . . . . .
C20 C 0.6940(2) 0.7072(2) 0.24879(16) 0.0223(5) Uani 1 1 d . . . . .
H20 H 0.640761 0.696187 0.195800 0.027 Uiso 1 1 calc R . . . .
C10 C 0.2562(2) 0.6089(2) 0.31925(16) 0.0252(6) Uani 1 1 d . . . . .
H10 H 0.273052 0.546923 0.283796 0.030 Uiso 1 1 calc R . . . .
C6 C 0.2086(2) 0.47516(19) 0.51784(14) 0.0188(5) Uani 1 1 d . . . . .
H6 H 0.188425 0.539398 0.479971 0.023 Uiso 1 1 calc R . . . .
C3 C -0.0360(2) 0.3641(2) 0.50311(16) 0.0246(6) Uani 1 1 d . . . . .
H3A H -0.122618 0.362948 0.478429 0.030 Uiso 1 1 calc R . . . .
H3B H -0.026006 0.298327 0.540145 0.030 Uiso 1 1 calc R . . . .
C21 C 0.7922(2) 0.6182(2) 0.24976(16) 0.0257(6) Uani 1 1 d . . . . .
H21 H 0.868493 0.629581 0.218380 0.031 Uiso 1 1 calc R . . . .
C4 C -0.0195(2) 0.4660(2) 0.55798(17) 0.0255(6) Uani 1 1 d . . . . .
H4A H -0.080704 0.464354 0.606672 0.031 Uiso 1 1 calc R . . . .
H4B H -0.038118 0.531559 0.522279 0.031 Uiso 1 1 calc R . . . .
C17 C 0.5965(2) 0.44644(19) 0.48577(16) 0.0207(5) Uani 1 1 d . . . . .
H17A H 0.622939 0.454359 0.547119 0.025 Uiso 1 1 calc R . . . .
H17B H 0.582605 0.367555 0.474177 0.025 Uiso 1 1 calc R . . . .
C5 C 0.1151(2) 0.4747(2) 0.59422(16) 0.0234(5) Uani 1 1 d . . . . .
H5A H 0.132936 0.411729 0.632871 0.028 Uiso 1 1 calc R . . . .
H5B H 0.124245 0.542966 0.628376 0.028 Uiso 1 1 calc R . . . .
C18 C 0.6147(3) 0.3797(2) 0.30690(17) 0.0289(6) Uani 1 1 d . . . . .
H18A H 0.674574 0.323370 0.326192 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.611263 0.380449 0.243335 0.043 Uiso 1 1 calc GR . . . .
H18C H 0.530376 0.363505 0.330163 0.043 Uiso 1 1 calc GR . . . .
C2 C 0.0606(2) 0.3603(2) 0.42960(17) 0.0277(6) Uani 1 1 d . . . . .
H2A H 0.042907 0.420506 0.388282 0.033 Uiso 1 1 calc R . . . .
H2B H 0.051678 0.290099 0.397916 0.033 Uiso 1 1 calc R . . . .
C11 C 0.1484(3) 0.6713(3) 0.30509(18) 0.0387(8) Uani 1 1 d . . . . .
H11 H 0.090993 0.651241 0.260353 0.046 Uiso 1 1 calc R . . . .
C13 C 0.2074(3) 0.7921(2) 0.41991(18) 0.0379(7) Uani 1 1 d . . . . .
H13 H 0.190901 0.855387 0.453967 0.045 Uiso 1 1 calc R . . . .
C12 C 0.1240(3) 0.7620(3) 0.35527(19) 0.0450(8) Uani 1 1 d . . . . .
H12 H 0.049670 0.804066 0.345408 0.054 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4437(18) . ?
S1 O2 1.4477(17) . ?
S1 C7 1.782(2) . ?
S1 C6 1.790(2) . ?
O3 C16 1.455(3) . ?
O3 C17 1.422(3) . ?
O4 C20 1.426(3) . ?
C8 C15 1.512(3) . ?
C8 C7 1.335(3) . ?
C8 C9 1.487(3) . ?
C1 C6 1.528(3) . ?
C1 C2 1.538(3) . ?
C15 C19 1.543(3) . ?
C15 C16 1.532(3) . ?
C7 C17 1.513(3) . ?
C14 C9 1.395(3) . ?
C14 C13 1.389(4) . ?
C19 C20 1.514(3) . ?
C22 C16 1.507(3) . ?
C22 C21 1.333(4) . ?
C9 C10 1.389(4) . ?
C16 C18 1.527(3) . ?
C20 C21 1.501(4) . ?
C10 C11 1.386(4) . ?
C6 C5 1.535(3) . ?
C3 C4 1.514(3) . ?
C3 C2 1.525(3) . ?
C4 C5 1.531(3) . ?
C11 C12 1.374(4) . ?
C13 C12 1.379(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.19(11) . . ?
O1 S1 C7 105.33(11) . . ?
O1 S1 C6 108.75(11) . . ?
O2 S1 C7 107.91(11) . . ?
O2 S1 C6 107.74(11) . . ?
C7 S1 C6 109.78(10) . . ?
C17 O3 C16 113.58(17) . . ?
C7 C8 C15 120.9(2) . . ?
C7 C8 C9 124.6(2) . . ?
C9 C8 C15 114.42(19) . . ?
C6 C1 C2 109.3(2) . . ?
C8 C15 C19 109.90(18) . . ?
C8 C15 C16 112.77(19) . . ?
C16 C15 C19 111.51(19) . . ?
C8 C7 S1 125.37(18) . . ?
C8 C7 C17 122.2(2) . . ?
C17 C7 S1 112.45(16) . . ?
C13 C14 C9 119.7(3) . . ?
C20 C19 C15 110.05(18) . . ?
C21 C22 C16 124.1(2) . . ?
C14 C9 C8 120.6(2) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 C14 119.6(2) . . ?
O3 C16 C15 108.24(17) . . ?
O3 C16 C22 104.93(18) . . ?
O3 C16 C18 110.88(19) . . ?
C22 C16 C15 112.2(2) . . ?
C22 C16 C18 109.1(2) . . ?
C18 C16 C15 111.3(2) . . ?
O4 C20 C19 112.4(2) . . ?
O4 C20 C21 112.4(2) . . ?
C21 C20 C19 109.5(2) . . ?
C11 C10 C9 119.9(3) . . ?
C1 C6 S1 111.41(16) . . ?
C1 C6 C5 111.63(19) . . ?
C5 C6 S1 108.89(16) . . ?
C4 C3 C2 111.3(2) . . ?
C22 C21 C20 123.3(2) . . ?
C3 C4 C5 111.5(2) . . ?
O3 C17 C7 111.28(18) . . ?
C4 C5 C6 108.5(2) . . ?
C3 C2 C1 112.0(2) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C13 C14 120.3(3) . . ?
C11 C12 C13 120.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.529
_oxdiff_exptl_absorpt_empirical_full_min 0.178
