# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc29yg5x
_database_code_depnum_ccdc_archive 'CCDC 2143469'
loop_
_audit_author_name
_audit_author_address
'Gulzar Bhat'
;Texas A and M University
United States of America
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-21
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O4'
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   16.3085(4)
_cell_length_b                   7.9252(2)
_cell_length_c                   21.3840(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2763.84(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2518
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.3841
_exptl_absorpt_correction_T_min  0.2655
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction
;
_exptl_absorpt_special_details   multi-scaan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1904
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.379
_diffrn_reflns_theta_min         5.425
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Venture (PHOTON III)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2398
_reflns_number_total             2518
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.718
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.073
_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)+(0.0980P)²+3.4804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1937
_refine_ls_wR_factor_ref         0.1962
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C7(H7a,H7b,H7c), C10(H10a,H10b,H10c)
;
_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
O3 O 0.40180(10) 0.1945(2) 0.42097(7) 0.0223(4) Uani 1 1 d . . . . .
O1 O 0.51681(9) 0.5207(2) 0.39430(7) 0.0223(4) Uani 1 1 d . . . . .
O2 O 0.36929(10) 0.40779(19) 0.35568(7) 0.0211(4) Uani 1 1 d . . . . .
O4 O 0.29406(12) 0.8014(3) 0.62961(9) 0.0398(5) Uani 1 1 d . . . . .
C8 C 0.38729(12) 0.2431(3) 0.36895(10) 0.0164(5) Uani 1 1 d . . . . .
C3 C 0.44996(13) 0.5863(3) 0.42386(9) 0.0182(5) Uani 1 1 d . . . . .
C2 C 0.45235(14) 0.7108(3) 0.46991(10) 0.0210(5) Uani 1 1 d . . . . .
H2 H 0.503699 0.753110 0.483819 0.025 Uiso 1 1 calc R U . . .
C4 C 0.37381(14) 0.5235(3) 0.40545(10) 0.0191(5) Uani 1 1 d . . . . .
C5 C 0.30234(13) 0.5812(3) 0.43181(10) 0.0209(5) Uani 1 1 d . . . . .
H5 H 0.251194 0.534901 0.419238 0.025 Uiso 1 1 calc R U . . .
C6 C 0.30490(15) 0.7077(3) 0.47706(11) 0.0238(5) Uani 1 1 d . . . . .
H6 H 0.255486 0.748724 0.495020 0.029 Uiso 1 1 calc R U . . .
C9 C 0.38612(13) 0.1368(3) 0.30961(10) 0.0184(5) Uani 1 1 d . . . . .
C11 C 0.40242(15) -0.0476(3) 0.32686(11) 0.0251(5) Uani 1 1 d . . . . .
H11A H 0.456506 -0.057079 0.346521 0.038 Uiso 1 1 calc R U . . .
H11B H 0.400949 -0.117096 0.288983 0.038 Uiso 1 1 calc R U . . .
H11C H 0.360252 -0.086581 0.356135 0.038 Uiso 1 1 calc R U . . .
C1 C 0.37978(15) 0.7737(3) 0.49579(11) 0.0242(5) Uani 1 1 d . . . . .
C12 C 0.30275(13) 0.1536(3) 0.27689(10) 0.0235(5) Uani 1 1 d . . . . .
H12A H 0.259333 0.113663 0.304903 0.035 Uiso 1 1 calc R U . . .
H12B H 0.302747 0.085654 0.238595 0.035 Uiso 1 1 calc R U . . .
H12C H 0.292952 0.272177 0.266275 0.035 Uiso 1 1 calc R U . . .
C7 C 0.59497(14) 0.5934(3) 0.40927(12) 0.0269(5) Uani 1 1 d . . . . .
H7A H 0.637852 0.537588 0.384707 0.040 Uiso 1 1 calc R U . . .
H7B H 0.606173 0.578042 0.453933 0.040 Uiso 1 1 calc R U . . .
H7C H 0.594266 0.714114 0.399389 0.040 Uiso 1 1 calc R U . . .
C10 C 0.45367(14) 0.2024(3) 0.26559(11) 0.0260(5) Uani 1 1 d . . . . .
H10A H 0.441451 0.319036 0.253580 0.039 Uiso 1 1 calc R U . . .
H10B H 0.455883 0.131535 0.228072 0.039 Uiso 1 1 calc R U . . .
H10C H 0.506694 0.198354 0.287113 0.039 Uiso 1 1 calc R U . . .
C15 C 0.33118(17) 0.9480(4) 0.65708(13) 0.0354(6) Uani 1 1 d . . . . .
H15A H 0.350596 0.939437 0.700831 0.042 Uiso 1 1 calc R U . . .
H15B H 0.309225 1.059840 0.645091 0.042 Uiso 1 1 calc R U . . .
C13 C 0.38295(18) 0.9125(3) 0.54459(13) 0.0362(7) Uani 1 1 d . . . . .
H13A H 0.435519 0.973952 0.540379 0.043 Uiso 1 1 calc R U . . .
H13B H 0.338092 0.993698 0.536341 0.043 Uiso 1 1 calc R U . . .
C14 C 0.37538(16) 0.8503(4) 0.60902(14) 0.0352(7) Uani 1 1 d . . . . .
H14 H 0.421589 0.778554 0.624446 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C8 1.201(3) . ?
O1 C3 1.363(3) . ?
O1 C7 1.435(3) . ?
O2 C8 1.367(3) . ?
O2 C4 1.407(3) . ?
O4 C15 1.436(3) . ?
O4 C14 1.450(3) . ?
C8 C9 1.523(3) . ?
C3 C2 1.394(3) . ?
C3 C4 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.399(3) . ?
C4 C5 1.373(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 H6 0.9500 . ?
C6 C1 1.388(3) . ?
C9 C11 1.530(3) . ?
C9 C12 1.535(3) . ?
C9 C10 1.540(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C1 C13 1.517(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.475(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.469(4) . ?
C14 H14 1.0000 . ?

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
C3 O1 C7 116.99(18) . . ?
C8 O2 C4 116.99(17) . . ?
C15 O4 C14 61.46(17) . . ?
O3 C8 O2 122.7(2) . . ?
O3 C8 C9 126.6(2) . . ?
O2 C8 C9 110.64(17) . . ?
O1 C3 C2 125.09(19) . . ?
O1 C3 C4 116.42(19) . . ?
C2 C3 C4 118.5(2) . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C4 O2 119.5(2) . . ?
C5 C4 O2 118.89(19) . . ?
C5 C4 C3 121.4(2) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.1 . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 H6 120.1 . . ?
C8 C9 C11 108.98(18) . . ?
C8 C9 C12 110.05(17) . . ?
C8 C9 C10 108.26(17) . . ?
C11 C9 C12 110.29(18) . . ?
C11 C9 C10 110.22(18) . . ?
C12 C9 C10 109.02(18) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C1 C13 120.1(2) . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 C13 120.1(2) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C15 H15A 117.8 . . ?
O4 C15 H15B 117.8 . . ?
O4 C15 C14 59.75(16) . . ?
H15A C15 H15B 114.9 . . ?
C14 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
C1 C13 H13A 108.9 . . ?
C1 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C1 113.5(2) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
O4 C14 C15 58.78(17) . . ?
O4 C14 C13 116.8(2) . . ?
O4 C14 H14 115.9 . . ?
C15 C14 H14 115.9 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 115.9 . . ?

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
O3 C8 C9 C11 2.8(3) . . . . ?
O3 C8 C9 C12 123.9(2) . . . . ?
O3 C8 C9 C10 -117.1(2) . . . . ?
O1 C3 C2 C1 177.7(2) . . . . ?
O1 C3 C4 O2 -4.4(3) . . . . ?
O1 C3 C4 C5 -179.62(19) . . . . ?
O2 C8 C9 C11 -177.31(17) . . . . ?
O2 C8 C9 C12 -56.2(2) . . . . ?
O2 C8 C9 C10 62.8(2) . . . . ?
O2 C4 C5 C6 -173.88(19) . . . . ?
O4 C15 C14 C13 104.5(3) . . . . ?
C8 O2 C4 C3 80.1(2) . . . . ?
C8 O2 C4 C5 -104.5(2) . . . . ?
C3 C2 C1 C6 2.2(3) . . . . ?
C3 C2 C1 C13 -178.3(2) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C2 C3 C4 O2 174.98(18) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C1 C13 C14 -98.9(3) . . . . ?
C4 O2 C8 O3 4.3(3) . . . . ?
C4 O2 C8 C9 -175.63(17) . . . . ?
C4 C3 C2 C1 -1.6(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C5 C6 C1 C2 -1.1(3) . . . . ?
C5 C6 C1 C13 179.5(2) . . . . ?
C6 C1 C13 C14 80.6(3) . . . . ?
C1 C13 C14 O4 -76.1(3) . . . . ?
C1 C13 C14 C15 -144.3(3) . . . . ?
C7 O1 C3 C2 -4.0(3) . . . . ?
C7 O1 C3 C4 175.30(19) . . . . ?
C15 O4 C14 C13 -111.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_audit_block_doi                 10.5517/ccdc.csd.cc29yg6y
_database_code_depnum_ccdc_archive 'CCDC 2143470'
loop_
_audit_author_name
_audit_author_address
'Gulzar Bhat'
;Texas A and M University
United States of America
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_audit_creation_date             2021-10-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O5 S'
_chemical_formula_sum            'C16 H20 O5 S'
_chemical_formula_weight         324.38
_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 0.0181 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.9329(5)
_cell_length_b                   6.1434(2)
_cell_length_c                   19.2618(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.7360(15)
_cell_angle_gamma                90
_cell_volume                     1637.34(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      70.049
_cell_measurement_theta_min      3.194
_shelx_estimated_absorpt_T_max   0.711
_shelx_estimated_absorpt_T_min   0.606
_exptl_absorpt_coefficient_mu    1.940
_exptl_absorpt_correction_T_max  0.3841
_exptl_absorpt_correction_T_min  0.2655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0856 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.6912.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.189
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20647
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.113
_diffrn_reflns_theta_min         3.716
_diffrn_ambient_temperature      110.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Venture (PHOTON III)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2946
_reflns_number_total             3093
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.055
_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)+(0.0514P)²+0.6948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0962
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.25625(2) 0.97211(6) 0.68815(2) 0.02868(13) Uani 1 1 d . . . . .
O1 O 0.83845(7) 0.55650(16) 0.61374(5) 0.0258(2) Uani 1 1 d . . . . .
O2 O 0.83494(8) 0.2812(2) 0.53634(6) 0.0373(3) Uani 1 1 d . . . . .
O3 O 0.72527(7) 0.27075(17) 0.66738(5) 0.0277(2) Uani 1 1 d . . . . .
O4 O 0.42135(7) 0.98890(16) 0.63819(6) 0.0268(2) Uani 1 1 d . . . . .
O5 O 0.38391(9) 1.29239(18) 0.69267(7) 0.0423(3) Uani 1 1 d . . . . .
C1 C 0.73816(10) 0.5810(2) 0.59901(7) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.67862(10) 0.4339(2) 0.62923(7) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.57918(10) 0.4635(2) 0.61874(7) 0.0233(3) Uani 1 1 d . . . . .
H3 H 0.537994 0.364892 0.639076 0.028 Uiso 1 1 calc R U . . .
C4 C 0.53932(10) 0.6377(2) 0.57842(7) 0.0244(3) Uani 1 1 d . . . . .
C5 C 0.59958(11) 0.7817(2) 0.54935(8) 0.0301(3) Uani 1 1 d . . . . .
H5 H 0.572614 0.900468 0.522130 0.036 Uiso 1 1 calc R U . . .
C6 C 0.70006(11) 0.7539(2) 0.55966(8) 0.0299(3) Uani 1 1 d . . . . .
H6 H 0.741323 0.853316 0.539728 0.036 Uiso 1 1 calc R U . . .
C7 C 0.87787(10) 0.3828(3) 0.58301(7) 0.0268(3) Uani 1 1 d . . . . .
C8 C 0.97955(11) 0.3328(3) 0.61783(8) 0.0320(3) Uani 1 1 d . . . . .
C9 C 1.03249(13) 0.5350(4) 0.64665(12) 0.0523(5) Uani 1 1 d . . . . .
H9A H 1.038448 0.637730 0.608466 0.078 Uiso 1 1 calc R U . . .
H9B H 1.097037 0.494649 0.668655 0.078 Uiso 1 1 calc R U . . .
H9C H 0.996207 0.603307 0.681443 0.078 Uiso 1 1 calc R U . . .
C10 C 1.03626(15) 0.2218(5) 0.56520(10) 0.0629(7) Uani 1 1 d . . . . .
H10A H 1.002072 0.090042 0.547501 0.094 Uiso 1 1 calc R U . . .
H10B H 1.100583 0.182505 0.587881 0.094 Uiso 1 1 calc R U . . .
H10C H 1.042746 0.321268 0.526247 0.094 Uiso 1 1 calc R U . . .
C11 C 0.96564(15) 0.1770(4) 0.67844(11) 0.0532(5) Uani 1 1 d . . . . .
H11A H 0.929664 0.251418 0.712226 0.080 Uiso 1 1 calc R U . . .
H11B H 1.028937 0.131932 0.701542 0.080 Uiso 1 1 calc R U . . .
H11C H 0.929456 0.048446 0.660131 0.080 Uiso 1 1 calc R U . . .
C12 C 0.66732(11) 0.1319(3) 0.70519(8) 0.0335(3) Uani 1 1 d . . . . .
H12A H 0.620331 0.054473 0.672222 0.050 Uiso 1 1 calc R U . . .
H12B H 0.633043 0.219786 0.736858 0.050 Uiso 1 1 calc R U . . .
H12C H 0.708925 0.026195 0.732382 0.050 Uiso 1 1 calc R U . . .
C13 C 0.43026(10) 0.6634(2) 0.56909(7) 0.0265(3) Uani 1 1 d . . . . .
H13A H 0.411206 0.758229 0.528232 0.032 Uiso 1 1 calc R U . . .
H13B H 0.400032 0.519157 0.559264 0.032 Uiso 1 1 calc R U . . .
C14 C 0.39243(9) 0.7605(2) 0.63289(7) 0.0224(3) Uani 1 1 d . . . . .
H14 H 0.421783 0.681324 0.675544 0.027 Uiso 1 1 calc R U . . .
C15 C 0.28290(10) 0.7537(2) 0.63014(8) 0.0278(3) Uani 1 1 d . . . . .
H15A H 0.260997 0.611750 0.646808 0.033 Uiso 1 1 calc R U . . .
H15B H 0.251550 0.779544 0.582015 0.033 Uiso 1 1 calc R U . . .
C16 C 0.36316(10) 1.1110(2) 0.67356(8) 0.0281(3) Uani 1 1 d . . . . .


_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 C15 1.8121(15) . ?
S1 C16 1.7675(15) . ?
O1 C1 1.4010(16) . ?
O1 C7 1.3664(18) . ?
O2 C7 1.1954(19) . ?
O3 C2 1.3621(17) . ?
O3 C12 1.4311(18) . ?
O4 C14 1.4601(16) . ?
O4 C16 1.3468(18) . ?
O5 C16 1.198(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.375(2) . ?
C2 C3 1.3885(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C4 C5 1.382(2) . ?
C4 C13 1.5173(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.5260(18) . ?
C8 C9 1.517(3) . ?
C8 C10 1.518(2) . ?
C8 C11 1.539(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5151(19) . ?
C14 H14 1.0000 . ?
C14 C15 1.5214(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C16 S1 C15 91.25(7) . . ?
C7 O1 C1 116.00(11) . . ?
C2 O3 C12 116.84(11) . . ?
C16 O4 C14 113.14(11) . . ?
C2 C1 O1 118.19(12) . . ?
C6 C1 O1 120.41(13) . . ?
C6 C1 C2 121.27(13) . . ?
O3 C2 C1 115.54(12) . . ?
O3 C2 C3 125.43(13) . . ?
C3 C2 C1 119.03(13) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.37(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C13 118.20(13) . . ?
C5 C4 C3 119.61(13) . . ?
C5 C4 C13 122.18(13) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.59(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.13(13) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O1 C7 C8 111.50(12) . . ?
O2 C7 O1 122.85(13) . . ?
O2 C7 C8 125.61(14) . . ?
C7 C8 C11 105.40(13) . . ?
C9 C8 C7 112.49(14) . . ?
C9 C8 C10 110.08(17) . . ?
C9 C8 C11 109.32(16) . . ?
C10 C8 C7 109.03(13) . . ?
C10 C8 C11 110.43(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.1 . . ?
C4 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C4 112.57(11) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
O4 C14 C13 108.39(11) . . ?
O4 C14 H14 109.1 . . ?
O4 C14 C15 107.23(11) . . ?
C13 C14 H14 109.1 . . ?
C13 C14 C15 113.82(11) . . ?
C15 C14 H14 109.1 . . ?
S1 C15 H15A 111.0 . . ?
S1 C15 H15B 111.0 . . ?
C14 C15 S1 103.62(9) . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
O4 C16 S1 112.35(10) . . ?
O5 C16 S1 125.28(12) . . ?
O5 C16 O4 122.37(14) . . ?

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
O1 C1 C2 O3 -3.77(18) . . . . ?
O1 C1 C2 C3 176.09(12) . . . . ?
O1 C1 C6 C5 -176.15(13) . . . . ?
O1 C7 C8 C9 -31.15(19) . . . . ?
O1 C7 C8 C10 -153.55(16) . . . . ?
O1 C7 C8 C11 87.89(17) . . . . ?
O2 C7 C8 C9 151.33(17) . . . . ?
O2 C7 C8 C10 28.9(2) . . . . ?
O2 C7 C8 C11 -89.62(19) . . . . ?
O3 C2 C3 C4 179.99(12) . . . . ?
O4 C14 C15 S1 -36.16(12) . . . . ?
C1 O1 C7 O2 13.9(2) . . . . ?
C1 O1 C7 C8 -163.67(12) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C13 -179.54(12) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C3 C4 C13 C14 77.41(16) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C13 C14 O4 70.43(14) . . . . ?
C4 C13 C14 C15 -170.36(12) . . . . ?
C5 C4 C13 C14 -101.65(16) . . . . ?
C6 C1 C2 O3 -179.53(13) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C7 O1 C1 C2 72.10(16) . . . . ?
C7 O1 C1 C6 -112.10(15) . . . . ?
C12 O3 C2 C1 173.35(12) . . . . ?
C12 O3 C2 C3 -6.5(2) . . . . ?
C13 C4 C5 C6 179.35(14) . . . . ?
C13 C14 C15 S1 -156.03(10) . . . . ?
C14 O4 C16 S1 -11.64(15) . . . . ?
C14 O4 C16 O5 167.91(14) . . . . ?
C15 S1 C16 O4 -9.62(11) . . . . ?
C15 S1 C16 O5 170.84(15) . . . . ?
C16 S1 C15 C14 25.98(10) . . . . ?
C16 O4 C14 C13 155.33(12) . . . . ?
C16 O4 C14 C15 32.05(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_audit_block_doi                 10.5517/ccdc.csd.cc29yg7z
_database_code_depnum_ccdc_archive 'CCDC 2143471'
loop_
_audit_author_name
_audit_author_address
'Gulzar Bhat'
;Texas A and M University
United States of America
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_audit_creation_date             2021-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O6'
_chemical_formula_sum            'C16 H20 O6'
_chemical_formula_weight         308.32
_chemical_absolute_configuration unk
_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 0.0181 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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.8206(5)
_cell_length_b                   6.2424(3)
_cell_length_c                   12.0066(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.9210(10)
_cell_angle_gamma                90
_cell_volume                     762.48(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9668
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      70.135
_cell_measurement_theta_min      3.916
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.669
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.5856
_exptl_absorpt_correction_T_min  0.4507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1077 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.7696.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.143
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19407
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.157
_diffrn_reflns_theta_min         3.916
_diffrn_ambient_temperature      110.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Venture (PHOTON III)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                2774
_reflns_number_total             2814
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.057
_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)+(0.0485P)²+0.1855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0802
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5(2)
 0.5(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_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
O5 O 0.45483(12) 0.3202(2) 0.73772(11) 0.0203(3) Uani 1 1 d . . . . .
O4 O 0.38969(13) 0.0514(2) 0.55775(12) 0.0231(3) Uani 1 1 d . . . . .
O6 O 0.36229(13) 0.0466(3) 0.80400(12) 0.0253(3) Uani 1 1 d . . . . .
O1 O 0.06774(14) 0.8123(3) 0.26255(12) 0.0266(3) Uani 1 1 d . . . . .
O2 O -0.06869(14) 0.8123(3) 0.07687(12) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.03158(19) 1.1164(3) 0.15698(14) 0.0386(4) Uani 1 1 d . . . . .
C3 C 0.30569(19) 0.2186(3) 0.54626(17) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.33724(18) 0.3575(3) 0.64380(16) 0.0196(4) Uani 1 1 d . . . . .
C1 C 0.11796(18) 0.4421(3) 0.44639(17) 0.0198(4) Uani 1 1 d . . . . .
C2 C 0.19525(19) 0.2620(3) 0.44805(17) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.172152 0.168592 0.381627 0.024 Uiso 1 1 calc R U . . .
C12 C 0.45926(19) 0.1414(3) 0.80545(16) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.0116(2) 0.9300(4) 0.16504(18) 0.0238(4) Uani 1 1 d . . . . .
C7 C -0.00125(19) 0.4875(3) 0.33745(17) 0.0225(4) Uani 1 1 d . . . . .
H7A H -0.049108 0.351786 0.309389 0.027 Uiso 1 1 calc R U . . .
H7B H -0.061084 0.585443 0.359496 0.027 Uiso 1 1 calc R U . . .
C10 C -0.0789(2) 0.5985(4) 0.11969(17) 0.0243(4) Uani 1 1 d . . . . .
H10A H -0.069337 0.488696 0.063698 0.029 Uiso 1 1 calc R U . . .
H10B H -0.164418 0.577865 0.131379 0.029 Uiso 1 1 calc R U . . .
C13 C 0.60017(19) 0.0771(3) 0.87681(17) 0.0223(4) Uani 1 1 d . . . . .
C8 C 0.03450(18) 0.5869(3) 0.23733(17) 0.0200(4) Uani 1 1 d . . . . .
H8 H 0.110399 0.508654 0.226806 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3723(2) -0.0764(4) 0.45439(19) 0.0262(4) Uani 1 1 d . . . . .
H11A H 0.377041 0.015362 0.389760 0.039 Uiso 1 1 calc R U . . .
H11B H 0.286230 -0.146866 0.430659 0.039 Uiso 1 1 calc R U . . .
H11C H 0.441592 -0.185196 0.472043 0.039 Uiso 1 1 calc R U . . .
C6 C 0.1523(2) 0.5785(4) 0.54321(17) 0.0242(4) Uani 1 1 d . . . . .
H6 H 0.100292 0.701701 0.542003 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2631(2) 0.5362(4) 0.64276(17) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.286616 0.630191 0.708926 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6991(2) 0.2566(4) 0.8895(2) 0.0310(5) Uani 1 1 d . . . . .
H16A H 0.700282 0.297050 0.810993 0.047 Uiso 1 1 calc R U . . .
H16B H 0.786709 0.207469 0.938695 0.047 Uiso 1 1 calc R U . . .
H16C H 0.673981 0.380807 0.926904 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6316(2) -0.1116(4) 0.8091(2) 0.0377(6) Uani 1 1 d . . . . .
H14A H 0.568018 -0.227015 0.802198 0.057 Uiso 1 1 calc R U . . .
H14B H 0.720487 -0.164188 0.852084 0.057 Uiso 1 1 calc R U . . .
H14C H 0.626446 -0.064252 0.729842 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6059(3) 0.0040(6) 1.0002(2) 0.0472(8) Uani 1 1 d . . . . .
H15A H 0.592408 0.127499 1.045157 0.071 Uiso 1 1 calc R U . . .
H15B H 0.692023 -0.059950 1.041926 0.071 Uiso 1 1 calc R U . . .
H15C H 0.536903 -0.102459 0.992622 0.071 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C4 1.402(2) . ?
O5 C12 1.372(2) . ?
O4 C3 1.360(2) . ?
O4 C11 1.433(2) . ?
O6 C12 1.200(3) . ?
O1 C9 1.340(2) . ?
O1 C8 1.458(3) . ?
O2 C9 1.337(3) . ?
O2 C10 1.448(3) . ?
O3 C9 1.194(3) . ?
C3 C4 1.403(3) . ?
C3 C2 1.390(3) . ?
C4 C5 1.372(3) . ?
C1 C2 1.397(3) . ?
C1 C7 1.518(3) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9500 . ?
C12 C13 1.526(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C8 1.525(3) . ?
C13 C16 1.521(3) . ?
C13 C14 1.534(3) . ?
C13 C15 1.532(3) . ?
C8 H8 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C5 1.399(3) . ?
C5 H5 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C12 O5 C4 116.77(15) . . ?
C3 O4 C11 116.96(15) . . ?
C9 O1 C8 109.97(15) . . ?
C9 O2 C10 109.46(15) . . ?
O4 C3 C4 115.20(17) . . ?
O4 C3 C2 125.99(17) . . ?
C2 C3 C4 118.81(18) . . ?
O5 C4 C3 117.68(17) . . ?
C5 C4 O5 120.67(17) . . ?
C5 C4 C3 121.33(17) . . ?
C2 C1 C7 119.41(18) . . ?
C6 C1 C2 119.63(18) . . ?
C6 C1 C7 120.95(18) . . ?
C3 C2 C1 120.42(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O5 C12 C13 111.90(16) . . ?
O6 C12 O5 122.61(17) . . ?
O6 C12 C13 125.45(18) . . ?
O2 C9 O1 111.65(18) . . ?
O3 C9 O1 124.4(2) . . ?
O3 C9 O2 123.9(2) . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C1 112.84(16) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
O2 C10 H10A 111.0 . . ?
O2 C10 H10B 111.0 . . ?
O2 C10 C8 103.74(15) . . ?
H10A C10 H10B 109.0 . . ?
C8 C10 H10A 111.0 . . ?
C8 C10 H10B 111.0 . . ?
C12 C13 C14 105.31(17) . . ?
C12 C13 C15 108.96(17) . . ?
C16 C13 C12 113.38(17) . . ?
C16 C13 C14 110.07(19) . . ?
C16 C13 C15 109.1(2) . . ?
C15 C13 C14 109.9(2) . . ?
O1 C8 C7 110.01(16) . . ?
O1 C8 C10 102.15(15) . . ?
O1 C8 H8 110.0 . . ?
C7 C8 C10 114.30(16) . . ?
C7 C8 H8 110.0 . . ?
C10 C8 H8 110.0 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C6 H6 119.8 . . ?
C1 C6 C5 120.47(19) . . ?
C5 C6 H6 119.8 . . ?
C4 C5 C6 119.31(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C4 C5 C6 174.54(18) . . . . ?
O5 C12 C13 C16 18.7(2) . . . . ?
O5 C12 C13 C14 -101.7(2) . . . . ?
O5 C12 C13 C15 140.4(2) . . . . ?
O4 C3 C4 O5 4.5(2) . . . . ?
O4 C3 C4 C5 178.08(18) . . . . ?
O4 C3 C2 C1 -178.77(18) . . . . ?
O6 C12 C13 C16 -163.5(2) . . . . ?
O6 C12 C13 C14 76.1(3) . . . . ?
O6 C12 C13 C15 -41.8(3) . . . . ?
O2 C10 C8 O1 16.84(18) . . . . ?
O2 C10 C8 C7 135.61(17) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 O5 C12 O6 -16.3(3) . . . . ?
C4 O5 C12 C13 161.61(16) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C1 C7 C8 O1 -76.0(2) . . . . ?
C1 C7 C8 C10 169.74(17) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C2 C3 C4 O5 -174.91(16) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C1 C7 C8 -78.3(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C12 O5 C4 C3 -70.2(2) . . . . ?
C12 O5 C4 C5 116.2(2) . . . . ?
C9 O1 C8 C7 -136.32(17) . . . . ?
C9 O1 C8 C10 -14.6(2) . . . . ?
C9 O2 C10 C8 -14.4(2) . . . . ?
C7 C1 C2 C3 179.26(17) . . . . ?
C7 C1 C6 C5 -179.44(19) . . . . ?
C10 O2 C9 O1 5.7(2) . . . . ?
C10 O2 C9 O3 -175.1(2) . . . . ?
C8 O1 C9 O2 6.3(2) . . . . ?
C8 O1 C9 O3 -172.9(2) . . . . ?
C11 O4 C3 C4 -171.27(17) . . . . ?
C11 O4 C3 C2 8.1(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C7 C8 100.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5(2)
2 0.5(2)
####################################################################### 
# 
# 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_4
_audit_block_doi                 10.5517/ccdc.csd.cc29yg80
_database_code_depnum_ccdc_archive 'CCDC 2143472'
loop_
_audit_author_name
_audit_author_address
'Gulzar Bhat'
;Texas A and M University
United States of America
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_audit_creation_date             2021-10-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O3 S'
_chemical_formula_sum            'C15 H20 O3 S'
_chemical_formula_weight         280.37
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   21.6035(6)
_cell_length_b                   7.9904(2)
_cell_length_c                   16.8357(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2906.19(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9601
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      27.495
_cell_measurement_theta_min      2.975
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.3787
_exptl_absorpt_correction_T_min  0.3348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1808 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.8841.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.247
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            159949
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         1.885
_diffrn_ambient_temperature      110.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Quest (PHOTON III)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6090
_reflns_number_total             6672
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
;
 Flack x determined using 2763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6672
_refine_ls_number_restraints     273
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.070
_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)+(0.0782P)²+3.0665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1629
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C14C, C14D}
3. Restrained distances
 C14A-C13 \\sim C14-C13
 with sigma of 0.02
 S1A-C15A \\sim S1-C15
 with sigma of 0.01
 C15A-C14A \\sim C15-C14
 with sigma of 0.01
 S1-C14 \\sim S1A-C14A
 with sigma of 0.01
 S1D-C15D \\sim S1C-C15C
 with sigma of 0.01
 C15C-C14C \\sim C15D-C14D
 with sigma of 0.01
 S1D-C14D \\sim S1C-C14C
 with sigma of 0.01
 C14C-C13C \\sim C14D-C13C
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
S1 \\sim C13 \\sim C14 \\sim C15 \\sim S1A \\sim C14A \\sim C15A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
S1C \\sim C13C \\sim C14C \\sim C15C \\sim S1D \\sim C14D \\sim C15D: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C14A) = Uanis(C14)
Uanis(S1) = Uanis(S1A)
Uanis(S1D) = Uanis(S1C)
Uanis(C14C) = Uanis(C14D)
Uanis(C15D) = Uanis(C15C)
Uanis(C15) = Uanis(C15A)
5. Rigid body (RIGU) restrains
 S1, C13, C14, C15, S1A, C14A, C15A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1C, C13C, C14C, C15C, S1D, C14D, C15D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(H13C)=Sof(H13D)=Sof(S1A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15C)=
 Sof(H15D)=1-FVAR(1)
 Sof(S1)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 FVAR(1)
 Sof(H13G)=Sof(H13H)=Sof(S1D)=Sof(C14D)=Sof(H14D)=Sof(C15D)=Sof(H15G)=
 Sof(H15H)=1-FVAR(2)
 Sof(S1C)=Sof(H13E)=Sof(H13F)=Sof(C14C)=Sof(H14C)=Sof(C15C)=Sof(H15E)=
 Sof(H15F)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C14(H14), C14C(H14C), C14A(H14A), C14D(H14D)
7.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13(H13C,H13D), C15(H15A,H15B), C13C(H13E,H13F), C13C(H13G,
 H13H), C15C(H15E,H15F), C15A(H15C,H15D), C15D(H15G,H15H)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C3C(H3C), C4C(H4C), C6C(H6C)
7.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C7C(H7CA,H7CB,H7CC), C10C(H10D,H10E,H10F), C11C(H11D,H11E,H11F),
 C12C(H12D,H12E,H12F)
;
_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 0.64714(14) 0.4865(4) 0.5512(2) 0.0422(6) Uani 0.572(4) 1 d D U P A 1
O1 O 0.39731(18) 0.7233(5) 0.7581(2) 0.0298(9) Uani 1 1 d . . . . .
O2 O 0.35798(15) 0.8481(4) 0.6183(3) 0.0312(9) Uani 1 1 d . . . . .
O3 O 0.42336(14) 1.0601(4) 0.6497(2) 0.0238(8) Uani 1 1 d . . . . .
C1 C 0.4268(2) 0.6657(6) 0.6934(3) 0.0225(10) Uani 1 1 d . . . . .
C2 C 0.4069(2) 0.7344(6) 0.6193(3) 0.0239(11) Uani 1 1 d . . . . .
C3 C 0.4331(3) 0.6791(7) 0.5480(3) 0.0303(12) Uani 1 1 d . . . . .
H3 H 0.420828 0.726559 0.498759 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4763(3) 0.5563(7) 0.5507(4) 0.0327(12) Uani 1 1 d . . . . .
H4 H 0.494983 0.521082 0.502423 0.039 Uiso 1 1 calc R U . . .
C5 C 0.4946(2) 0.4789(6) 0.6219(4) 0.0285(11) Uani 1 1 d . . . . .
C6 C 0.4712(2) 0.5355(6) 0.6910(4) 0.0236(10) Uani 1 1 d . . . . .
H6 H 0.484779 0.486651 0.739420 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4129(3) 0.6406(7) 0.8321(3) 0.0374(14) Uani 1 1 d . . . . .
H7A H 0.406453 0.519780 0.826544 0.056 Uiso 1 1 calc R U . . .
H7B H 0.386377 0.683688 0.874714 0.056 Uiso 1 1 calc R U . . .
H7C H 0.456347 0.662527 0.845162 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3707(2) 1.0104(6) 0.6354(3) 0.0222(10) Uani 1 1 d . . . . .
C9 C 0.3129(2) 1.1161(6) 0.6354(3) 0.0205(9) Uani 1 1 d . . . . .
C10 C 0.2683(2) 1.0484(7) 0.6974(3) 0.0295(11) Uani 1 1 d . . . . .
H10A H 0.261366 0.928821 0.688002 0.044 Uiso 1 1 calc R U . . .
H10B H 0.228893 1.108429 0.693733 0.044 Uiso 1 1 calc R U . . .
H10C H 0.286030 1.064233 0.750481 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3304(2) 1.3013(6) 0.6521(4) 0.0265(11) Uani 1 1 d . . . . .
H11A H 0.344076 1.312564 0.707402 0.040 Uiso 1 1 calc R U . . .
H11B H 0.294284 1.372840 0.643099 0.040 Uiso 1 1 calc R U . . .
H11C H 0.364032 1.335292 0.616499 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2809(2) 1.0994(6) 0.5535(3) 0.0251(10) Uani 1 1 d . . . . .
H12A H 0.308210 1.144071 0.512125 0.038 Uiso 1 1 calc R U . . .
H12B H 0.242013 1.162450 0.553889 0.038 Uiso 1 1 calc R U . . .
H12C H 0.272294 0.981189 0.542711 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5418(2) 0.3402(8) 0.6220(5) 0.0393(14) Uani 1 1 d D U . . .
H13A H 0.531641 0.260919 0.665249 0.047 Uiso 0.572(4) 1 calc R U P A 1
H13B H 0.538843 0.278489 0.571132 0.047 Uiso 0.572(4) 1 calc R U P A 1
H13C H 0.558511 0.329717 0.676516 0.047 Uiso 0.428(4) 1 calc R U P A 2
H13D H 0.520189 0.234183 0.609464 0.047 Uiso 0.428(4) 1 calc R U P A 2
C14 C 0.6067(4) 0.3988(12) 0.6326(6) 0.0293(12) Uani 0.572(4) 1 d D U P A 1
H14 H 0.614912 0.454717 0.684682 0.035 Uiso 0.572(4) 1 calc R U P A 1
C15 C 0.6656(10) 0.2827(18) 0.5983(13) 0.0321(17) Uani 0.572(4) 1 d D U P A 1
H15A H 0.655442 0.179548 0.568469 0.039 Uiso 0.572(4) 1 calc R U P A 1
H15B H 0.703534 0.275822 0.631179 0.039 Uiso 0.572(4) 1 calc R U P A 1
S1C S 0.66726(15) -0.2315(4) 0.3997(2) 0.0346(6) Uani 0.558(4) 1 d D U P B 1
O1C O 0.39737(16) 0.2231(4) 0.2360(3) 0.0280(8) Uani 1 1 d . . . . .
O2C O 0.35888(15) 0.3479(4) 0.3773(3) 0.0299(9) Uani 1 1 d . . . . .
O3C O 0.42204(16) 0.5572(4) 0.3438(3) 0.0291(8) Uani 1 1 d . . . . .
C1C C 0.4245(2) 0.1604(6) 0.3039(4) 0.0241(10) Uani 1 1 d . . . . .
C2C C 0.4078(2) 0.2313(6) 0.3747(4) 0.0271(11) Uani 1 1 d . . . . .
C3C C 0.4324(2) 0.1815(6) 0.4438(4) 0.0314(13) Uani 1 1 d . . . . .
H3C H 0.419868 0.235438 0.491508 0.038 Uiso 1 1 calc R U . . .
C4C C 0.4766(2) 0.0500(6) 0.4478(4) 0.0281(11) Uani 1 1 d . . . . .
H4C H 0.492348 0.011145 0.497155 0.034 Uiso 1 1 calc R U . . .
C5C C 0.4957(2) -0.0187(6) 0.3765(4) 0.0258(11) Uani 1 1 d . . . . .
C6C C 0.4695(2) 0.0401(7) 0.3029(4) 0.0268(11) Uani 1 1 d . . . . .
H6C H 0.483497 -0.004536 0.253813 0.032 Uiso 1 1 calc R U . . .
C7C C 0.4119(2) 0.1429(7) 0.1640(3) 0.0302(12) Uani 1 1 d . . . . .
H7CA H 0.389342 0.196954 0.120468 0.045 Uiso 1 1 calc R U . . .
H7CB H 0.399827 0.024811 0.167154 0.045 Uiso 1 1 calc R U . . .
H7CC H 0.456469 0.150984 0.154233 0.045 Uiso 1 1 calc R U . . .
C8C C 0.3725(2) 0.5114(6) 0.3585(3) 0.0183(9) Uani 1 1 d . . . . .
C9C C 0.3124(2) 0.6163(6) 0.3619(3) 0.0235(10) Uani 1 1 d . . . . .
C10C C 0.2680(2) 0.5529(7) 0.2949(4) 0.0356(13) Uani 1 1 d . . . . .
H10D H 0.232594 0.628973 0.290476 0.053 Uiso 1 1 calc R U . . .
H10E H 0.253302 0.440278 0.308057 0.053 Uiso 1 1 calc R U . . .
H10F H 0.290341 0.549892 0.244259 0.053 Uiso 1 1 calc R U . . .
C11C C 0.2825(2) 0.6003(7) 0.4434(4) 0.0292(12) Uani 1 1 d . . . . .
H11D H 0.269685 0.484063 0.452057 0.044 Uiso 1 1 calc R U . . .
H11E H 0.246188 0.673603 0.446210 0.044 Uiso 1 1 calc R U . . .
H11F H 0.312332 0.632958 0.484416 0.044 Uiso 1 1 calc R U . . .
C12C C 0.3284(2) 0.7959(6) 0.3454(3) 0.0267(11) Uani 1 1 d . . . . .
H12D H 0.350689 0.803506 0.294776 0.040 Uiso 1 1 calc R U . . .
H12E H 0.354656 0.839082 0.388182 0.040 Uiso 1 1 calc R U . . .
H12F H 0.290332 0.862196 0.342329 0.040 Uiso 1 1 calc R U . . .
C13C C 0.5424(2) -0.1607(6) 0.3750(5) 0.0342(13) Uani 1 1 d D U . . .
H13E H 0.540245 -0.222813 0.425837 0.041 Uiso 0.558(4) 1 calc R U P B 1
H13F H 0.531584 -0.239199 0.331721 0.041 Uiso 0.558(4) 1 calc R U P B 1
H13G H 0.540245 -0.222813 0.425837 0.041 Uiso 0.442(4) 1 calc R U P B 2
H13H H 0.531584 -0.239199 0.331721 0.041 Uiso 0.442(4) 1 calc R U P B 2
C14C C 0.6064(2) -0.0991(6) 0.3629(3) 0.0236(8) Uani 0.558(4) 1 d D U P B 1
H14C H 0.614036 -0.060898 0.307208 0.028 Uiso 0.558(4) 1 calc R U P B 1
C15C C 0.6494(5) -0.0170(16) 0.4219(7) 0.0327(18) Uani 0.558(4) 1 d D U P B 1
H15E H 0.632564 0.007547 0.475337 0.039 Uiso 0.558(4) 1 calc R U P B 1
H15F H 0.678142 0.069243 0.401316 0.039 Uiso 0.558(4) 1 calc R U P B 1
S1A S 0.6665(4) 0.2697(8) 0.5946(5) 0.0422(6) Uani 0.428(4) 1 d D U P A 2
C14A C 0.5916(4) 0.3565(12) 0.5698(6) 0.0293(12) Uani 0.428(4) 1 d D U P A 2
H14A H 0.580278 0.346171 0.512478 0.035 Uiso 0.428(4) 1 calc R U P A 2
C15A C 0.6475(6) 0.4930(16) 0.5878(10) 0.0321(17) Uani 0.428(4) 1 d D U P A 2
H15C H 0.645322 0.557245 0.638031 0.039 Uiso 0.428(4) 1 calc R U P A 2
H15D H 0.664403 0.556229 0.542120 0.039 Uiso 0.428(4) 1 calc R U P A 2
S1D S 0.64568(19) -0.0114(6) 0.4471(2) 0.0346(6) Uani 0.442(4) 1 d D U P B 2
C14D C 0.6064(2) -0.0991(6) 0.3629(3) 0.0236(8) Uani 0.442(4) 1 d D U P B 2
H14D H 0.612711 -0.035801 0.312326 0.028 Uiso 0.442(4) 1 calc R U P B 2
C15D C 0.6608(7) -0.1988(17) 0.3884(11) 0.0327(18) Uani 0.442(4) 1 d D U P B 2
H15G H 0.697618 -0.197456 0.353399 0.039 Uiso 0.442(4) 1 calc R U P B 2
H15H H 0.652601 -0.308211 0.413920 0.039 Uiso 0.442(4) 1 calc R U P B 2


_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 C14 1.771(9) . ?
S1 C15 1.855(13) . ?
O1 C1 1.343(7) . ?
O1 C7 1.451(6) . ?
O2 C2 1.394(5) . ?
O2 C8 1.356(6) . ?
O3 C8 1.229(6) . ?
C1 C2 1.429(7) . ?
C1 C6 1.416(6) . ?
C2 C3 1.398(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.355(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.405(8) . ?
C5 C6 1.347(9) . ?
C5 C13 1.506(7) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.506(7) . ?
C9 C10 1.520(7) . ?
C9 C11 1.553(6) . ?
C9 C12 1.547(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C13 C14 1.488(10) . ?
C13 C14A 1.395(10) . ?
C14 H14 1.0000 . ?
C14 C15 1.678(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
S1C C14C 1.797(5) . ?
S1C C15C 1.796(12) . ?
O1C C1C 1.379(6) . ?
O1C C7C 1.406(7) . ?
O2C C2C 1.409(6) . ?
O2C C8C 1.376(6) . ?
O3C C8C 1.158(6) . ?
C1C C2C 1.369(8) . ?
C1C C6C 1.368(7) . ?
C2C C3C 1.339(9) . ?
C3C H3C 0.9500 . ?
C3C C4C 1.422(7) . ?
C4C H4C 0.9500 . ?
C4C C5C 1.382(9) . ?
C5C C6C 1.441(9) . ?
C5C C13C 1.518(7) . ?
C6C H6C 0.9500 . ?
C7C H7CA 0.9800 . ?
C7C H7CB 0.9800 . ?
C7C H7CC 0.9800 . ?
C8C C9C 1.546(6) . ?
C9C C10C 1.565(7) . ?
C9C C11C 1.523(7) . ?
C9C C12C 1.502(7) . ?
C10C H10D 0.9800 . ?
C10C H10E 0.9800 . ?
C10C H10F 0.9800 . ?
C11C H11D 0.9800 . ?
C11C H11E 0.9800 . ?
C11C H11F 0.9800 . ?
C12C H12D 0.9800 . ?
C12C H12E 0.9800 . ?
C12C H12F 0.9800 . ?
C13C H13E 0.9900 . ?
C13C H13F 0.9900 . ?
C13C H13G 0.9900 . ?
C13C H13H 0.9900 . ?
C13C C14C 1.483(7) . ?
C13C C14D 1.483(7) . ?
C14C H14C 1.0000 . ?
C14C C15C 1.510(12) . ?
C15C H15E 0.9900 . ?
C15C H15F 0.9900 . ?
S1A C14A 1.808(10) . ?
S1A C15A 1.834(11) . ?
C14A H14A 1.0000 . ?
C14A C15A 1.655(15) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
S1D C14D 1.794(6) . ?
S1D C15D 1.824(14) . ?
C14D H14D 1.0000 . ?
C14D C15D 1.482(13) . ?
C15D H15G 0.9900 . ?
C15D H15H 0.9900 . ?

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
C14 S1 C15 55.1(6) . . ?
C1 O1 C7 115.5(4) . . ?
C8 O2 C2 117.9(4) . . ?
O1 C1 C2 115.7(4) . . ?
O1 C1 C6 126.6(5) . . ?
C6 C1 C2 117.5(5) . . ?
O2 C2 C1 119.3(5) . . ?
O2 C2 C3 120.2(5) . . ?
C3 C2 C1 120.4(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.7(6) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C13 121.0(6) . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 C13 120.0(6) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.7(5) . . ?
C5 C6 H6 119.2 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 111.6(4) . . ?
O3 C8 O2 122.5(5) . . ?
O3 C8 C9 125.9(4) . . ?
C8 C9 C10 108.9(4) . . ?
C8 C9 C11 109.4(4) . . ?
C8 C9 C12 108.8(4) . . ?
C10 C9 C11 111.6(5) . . ?
C10 C9 C12 107.3(4) . . ?
C12 C9 C11 110.6(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 108.8 . . ?
C5 C13 H13B 108.8 . . ?
C5 C13 H13C 108.1 . . ?
C5 C13 H13D 108.1 . . ?
H13A C13 H13B 107.7 . . ?
H13C C13 H13D 107.3 . . ?
C14 C13 C5 114.0(6) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C14A C13 C5 116.9(6) . . ?
C14A C13 H13C 108.1 . . ?
C14A C13 H13D 108.1 . . ?
S1 C14 H14 114.4 . . ?
C13 C14 S1 119.7(7) . . ?
C13 C14 H14 114.4 . . ?
C13 C14 C15 120.0(10) . . ?
C15 C14 S1 65.0(6) . . ?
C15 C14 H14 114.4 . . ?
S1 C15 H15A 117.8 . . ?
S1 C15 H15B 117.8 . . ?
C14 C15 S1 59.9(6) . . ?
C14 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
H15A C15 H15B 114.9 . . ?
C15C S1C C14C 49.7(4) . . ?
C1C O1C C7C 117.0(4) . . ?
C8C O2C C2C 117.4(3) . . ?
C2C C1C O1C 117.4(4) . . ?
C6C C1C O1C 123.2(5) . . ?
C6C C1C C2C 119.3(5) . . ?
C1C C2C O2C 119.9(5) . . ?
C3C C2C O2C 117.8(5) . . ?
C3C C2C C1C 122.0(5) . . ?
C2C C3C H3C 119.1 . . ?
C2C C3C C4C 121.8(5) . . ?
C4C C3C H3C 119.1 . . ?
C3C C4C H4C 121.5 . . ?
C5C C4C C3C 117.0(5) . . ?
C5C C4C H4C 121.5 . . ?
C4C C5C C6C 120.0(5) . . ?
C4C C5C C13C 120.6(5) . . ?
C6C C5C C13C 119.4(6) . . ?
C1C C6C C5C 119.9(5) . . ?
C1C C6C H6C 120.1 . . ?
C5C C6C H6C 120.1 . . ?
O1C C7C H7CA 109.5 . . ?
O1C C7C H7CB 109.5 . . ?
O1C C7C H7CC 109.5 . . ?
H7CA C7C H7CB 109.5 . . ?
H7CA C7C H7CC 109.5 . . ?
H7CB C7C H7CC 109.5 . . ?
O2C C8C C9C 109.0(4) . . ?
O3C C8C O2C 123.2(4) . . ?
O3C C8C C9C 127.8(4) . . ?
C8C C9C C10C 108.2(4) . . ?
C11C C9C C8C 110.1(4) . . ?
C11C C9C C10C 111.2(4) . . ?
C12C C9C C8C 108.5(4) . . ?
C12C C9C C10C 108.5(5) . . ?
C12C C9C C11C 110.2(5) . . ?
C9C C10C H10D 109.5 . . ?
C9C C10C H10E 109.5 . . ?
C9C C10C H10F 109.5 . . ?
H10D C10C H10E 109.5 . . ?
H10D C10C H10F 109.5 . . ?
H10E C10C H10F 109.5 . . ?
C9C C11C H11D 109.5 . . ?
C9C C11C H11E 109.5 . . ?
C9C C11C H11F 109.5 . . ?
H11D C11C H11E 109.5 . . ?
H11D C11C H11F 109.5 . . ?
H11E C11C H11F 109.5 . . ?
C9C C12C H12D 109.5 . . ?
C9C C12C H12E 109.5 . . ?
C9C C12C H12F 109.5 . . ?
H12D C12C H12E 109.5 . . ?
H12D C12C H12F 109.5 . . ?
H12E C12C H12F 109.5 . . ?
C5C C13C H13E 109.2 . . ?
C5C C13C H13F 109.2 . . ?
C5C C13C H13G 109.2 . . ?
C5C C13C H13H 109.2 . . ?
H13E C13C H13F 107.9 . . ?
H13G C13C H13H 107.9 . . ?
C14C C13C C5C 112.0(4) . . ?
C14C C13C H13E 109.2 . . ?
C14C C13C H13F 109.2 . . ?
C14D C13C C5C 112.0(4) . . ?
C14D C13C H13G 109.2 . . ?
C14D C13C H13H 109.2 . . ?
S1C C14C H14C 112.5 . . ?
C13C C14C S1C 116.1(4) . . ?
C13C C14C H14C 112.5 . . ?
C13C C14C C15C 128.9(6) . . ?
C15C C14C S1C 65.1(5) . . ?
C15C C14C H14C 112.5 . . ?
S1C C15C H15E 117.2 . . ?
S1C C15C H15F 117.2 . . ?
C14C C15C S1C 65.2(5) . . ?
C14C C15C H15E 117.2 . . ?
C14C C15C H15F 117.2 . . ?
H15E C15C H15F 114.3 . . ?
C14A S1A C15A 54.0(5) . . ?
C13 C14A S1A 120.6(7) . . ?
C13 C14A H14A 114.2 . . ?
C13 C14A C15A 120.6(9) . . ?
S1A C14A H14A 114.2 . . ?
C15A C14A S1A 63.8(5) . . ?
C15A C14A H14A 114.2 . . ?
S1A C15A H15C 117.5 . . ?
S1A C15A H15D 117.5 . . ?
C14A C15A S1A 62.2(6) . . ?
C14A C15A H15C 117.5 . . ?
C14A C15A H15D 117.5 . . ?
H15C C15A H15D 114.6 . . ?
C14D S1D C15D 48.4(5) . . ?
C13C C14D S1D 117.5(4) . . ?
C13C C14D H14D 114.3 . . ?
S1D C14D H14D 114.3 . . ?
C15D C14D C13C 121.4(8) . . ?
C15D C14D S1D 66.8(6) . . ?
C15D C14D H14D 114.3 . . ?
S1D C15D H15G 117.3 . . ?
S1D C15D H15H 117.3 . . ?
C14D C15D S1D 64.8(5) . . ?
C14D C15D H15G 117.3 . . ?
C14D C15D H15H 117.3 . . ?
H15G C15D H15H 114.3 . . ?

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
O1 C1 C2 O2 -2.6(6) . . . . ?
O1 C1 C2 C3 -177.9(5) . . . . ?
O1 C1 C6 C5 175.0(5) . . . . ?
O2 C2 C3 C4 -173.5(4) . . . . ?
O2 C8 C9 C10 59.9(6) . . . . ?
O2 C8 C9 C11 -177.9(5) . . . . ?
O2 C8 C9 C12 -56.9(5) . . . . ?
O3 C8 C9 C10 -119.5(6) . . . . ?
O3 C8 C9 C11 2.8(7) . . . . ?
O3 C8 C9 C12 123.8(6) . . . . ?
C1 C2 C3 C4 1.7(8) . . . . ?
C2 O2 C8 O3 1.8(8) . . . . ?
C2 O2 C8 C9 -177.6(5) . . . . ?
C2 C1 C6 C5 0.8(7) . . . . ?
C2 C3 C4 C5 1.9(8) . . . . ?
C3 C4 C5 C6 -4.1(8) . . . . ?
C3 C4 C5 C13 178.6(5) . . . . ?
C4 C5 C6 C1 2.7(7) . . . . ?
C4 C5 C13 C14 91.5(8) . . . . ?
C4 C5 C13 C14A 39.0(9) . . . . ?
C5 C13 C14 S1 -78.4(8) . . . . ?
C5 C13 C14 C15 -155.0(10) . . . . ?
C5 C13 C14A S1A 149.0(7) . . . . ?
C5 C13 C14A C15A 73.2(11) . . . . ?
C6 C1 C2 O2 172.2(4) . . . . ?
C6 C1 C2 C3 -3.1(7) . . . . ?
C6 C5 C13 C14 -85.8(8) . . . . ?
C6 C5 C13 C14A -138.2(7) . . . . ?
C7 O1 C1 C2 173.6(4) . . . . ?
C7 O1 C1 C6 -0.6(7) . . . . ?
C8 O2 C2 C1 81.9(6) . . . . ?
C8 O2 C2 C3 -102.7(6) . . . . ?
C13 C5 C6 C1 179.9(5) . . . . ?
C13 C14 C15 S1 111.3(9) . . . . ?
C13 C14A C15A S1A 111.6(9) . . . . ?
C15 S1 C14 C13 -111.6(12) . . . . ?
O1C C1C C2C O2C 8.2(6) . . . . ?
O1C C1C C2C C3C -178.7(5) . . . . ?
O1C C1C C6C C5C 179.8(4) . . . . ?
O2C C2C C3C C4C 172.3(4) . . . . ?
O2C C8C C9C C10C -65.3(5) . . . . ?
O2C C8C C9C C11C 56.5(5) . . . . ?
O2C C8C C9C C12C 177.2(5) . . . . ?
O3C C8C C9C C10C 115.5(6) . . . . ?
O3C C8C C9C C11C -122.7(6) . . . . ?
O3C C8C C9C C12C -2.0(8) . . . . ?
C1C C2C C3C C4C -0.9(8) . . . . ?
C2C O2C C8C O3C -2.9(8) . . . . ?
C2C O2C C8C C9C 177.9(5) . . . . ?
C2C C1C C6C C5C 4.4(7) . . . . ?
C2C C3C C4C C5C 3.3(8) . . . . ?
C3C C4C C5C C6C -1.8(7) . . . . ?
C3C C4C C5C C13C -179.5(4) . . . . ?
C4C C5C C6C C1C -1.9(7) . . . . ?
C4C C5C C13C C14C -95.4(7) . . . . ?
C4C C5C C13C C14D -95.4(7) . . . . ?
C5C C13C C14C S1C 155.1(4) . . . . ?
C5C C13C C14C C15C 77.0(10) . . . . ?
C5C C13C C14D S1D 78.5(6) . . . . ?
C5C C13C C14D C15D 156.9(9) . . . . ?
C6C C1C C2C O2C -176.1(4) . . . . ?
C6C C1C C2C C3C -3.0(7) . . . . ?
C6C C5C C13C C14C 86.9(6) . . . . ?
C6C C5C C13C C14D 86.9(6) . . . . ?
C7C O1C C1C C2C -176.2(4) . . . . ?
C7C O1C C1C C6C 8.2(6) . . . . ?
C8C O2C C2C C1C -83.1(6) . . . . ?
C8C O2C C2C C3C 103.4(6) . . . . ?
C13C C5C C6C C1C 175.8(4) . . . . ?
C13C C14C C15C S1C 104.4(6) . . . . ?
C13C C14D C15D S1D -109.1(6) . . . . ?
C15C S1C C14C C13C -122.9(7) . . . . ?
C15A S1A C14A C13 -111.6(11) . . . . ?
C15D S1D C14D C13C 114.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT111_msn04               
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: We did see the additional symmetry and Pbca as suggested
space group. However, our trials in Pbca resulted in much higher
reliability factors of R1 (8.71) and wR2 (25.61). We also tried
monoclinic space groups and the results did not improve.
;
_vrf_PLAT112_msn04               
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         b        100 %Fit  
RESPONSE: We did see the additional symmetry and Pbca as suggested
space group. However, our trials in Pbca resulted in much higher
reliability factors of R1 (8.71) and wR2 (25.61). We also tried
monoclinic space groups and the results did not improve.
;
_vrf_PLAT113_msn04               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pbca Check 
RESPONSE: We did see the additional symmetry and Pbca as suggested
space group. However, our trials in Pbca resulted in much higher
reliability factors of R1 (8.71) and wR2 (25.61). We also tried
monoclinic space groups and the results did not improve.
;
_vrf_PLAT230_msn04               
;
PROBLEM: Hirshfeld Test Diff for    C2C      --C3C      .        7.3 s.u.  
RESPONSE: Slightly elongated ellipsoids on other atoms suggested minor
disorder in addition to the existing disorder in (C14, C15, S1) and
(C14c, C15c, S1c). Appropriate restraints and constraints were added 
to keep the bond distances, angles, and thermal ellipsoids meaningful. 
No further efforts were made to model any additional disorder.
;

#===END
