# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_oqm-s-lactone-2
_database_code_depnum_ccdc_archive 'CCDC 1969971'
loop_
_audit_author_name
_audit_author_address
'CHANDAN GHARUI'
;IIT GUWAHATI
India
;
_audit_update_record             
;
2019-12-04 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 O2 S'
_chemical_formula_weight         256.31

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_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                   7.5756(8)
_cell_length_b                   8.7063(6)
_cell_length_c                   19.340(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1275.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3353
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3141
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.1225
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2140
_reflns_number_gt                1132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0291P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration S
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.5086(3) 0.65966(17) 0.65282(9) 0.0659(5) Uani 1 1 d . . .
O8 O 0.5758(5) 0.5274(4) 0.4931(2) 0.0525(12) Uani 1 1 d . . .
O18 O 0.4688(6) 0.7584(4) 0.4772(2) 0.0719(14) Uani 1 1 d . . .
C2 C 0.6343(7) 0.3867(6) 0.5990(3) 0.0391(15) Uani 1 1 d . . .
C7 C 0.5777(8) 0.3897(6) 0.5312(3) 0.0465(16) Uani 1 1 d . . .
C1 C 0.6973(8) 0.5333(6) 0.6323(3) 0.0473(17) Uani 1 1 d . . .
H1 H 0.7708 0.5871 0.5984 0.057 Uiso 1 1 calc R . .
C9 C 0.4715(9) 0.6467(7) 0.5132(3) 0.0512(16) Uani 1 1 d . . .
C12 C 0.8084(9) 0.5084(7) 0.6960(3) 0.0553(18) Uani 1 1 d . . .
C3 C 0.6346(7) 0.2449(6) 0.6317(3) 0.0497(17) Uani 1 1 d . . .
H3 H 0.6720 0.2379 0.6774 0.060 Uiso 1 1 calc R . .
C6 C 0.5242(8) 0.2613(7) 0.4955(3) 0.0556(17) Uani 1 1 d . . .
H6 H 0.4869 0.2681 0.4497 0.067 Uiso 1 1 calc R . .
C5 C 0.5276(9) 0.1218(6) 0.5296(4) 0.0608(19) Uani 1 1 d . . .
H5 H 0.4939 0.0331 0.5063 0.073 Uiso 1 1 calc R . .
C10 C 0.3733(9) 0.6255(6) 0.5785(3) 0.0598(19) Uani 1 1 d . . .
H10A H 0.3278 0.5215 0.5804 0.072 Uiso 1 1 calc R . .
H10B H 0.2735 0.6953 0.5794 0.072 Uiso 1 1 calc R . .
C17 C 0.7402(10) 0.5036(7) 0.7618(4) 0.065(2) Uani 1 1 d . . .
H17 H 0.6201 0.5216 0.7677 0.078 Uiso 1 1 calc R . .
C4 C 0.5798(9) 0.1125(7) 0.5971(4) 0.061(2) Uani 1 1 d . . .
H4 H 0.5787 0.0184 0.6199 0.074 Uiso 1 1 calc R . .
C13 C 0.9893(10) 0.4836(8) 0.6885(4) 0.079(2) Uani 1 1 d . . .
H13 H 1.0408 0.4894 0.6449 0.095 Uiso 1 1 calc R . .
C16 C 0.8413(11) 0.4735(8) 0.8193(4) 0.086(3) Uani 1 1 d . . .
H16 H 0.7916 0.4719 0.8633 0.103 Uiso 1 1 calc R . .
C15 C 1.0214(12) 0.4453(8) 0.8096(4) 0.087(3) Uani 1 1 d . . .
H15 H 1.0931 0.4228 0.8473 0.104 Uiso 1 1 calc R . .
C14 C 1.0914(11) 0.4508(9) 0.7448(5) 0.099(3) Uani 1 1 d . . .
H14 H 1.2113 0.4319 0.7388 0.118 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
S11 C10 1.789(6) . ?
S11 C1 1.847(6) . ?
O8 C9 1.362(6) . ?
O8 C7 1.407(6) . ?
O18 C9 1.196(6) . ?
C2 C7 1.380(7) . ?
C2 C3 1.387(6) . ?
C2 C1 1.508(7) . ?
C7 C6 1.376(7) . ?
C1 C12 1.506(8) . ?
C9 C10 1.477(8) . ?
C12 C17 1.375(8) . ?
C12 C13 1.395(9) . ?
C3 C4 1.396(7) . ?
C6 C5 1.382(7) . ?
C5 C4 1.367(8) . ?
C17 C16 1.376(9) . ?
C13 C14 1.366(9) . ?
C16 C15 1.399(10) . ?
C15 C14 1.361(10) . ?

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
C10 S11 C1 99.9(3) . . ?
C9 O8 C7 120.4(5) . . ?
C7 C2 C3 116.8(5) . . ?
C7 C2 C1 119.3(5) . . ?
C3 C2 C1 123.9(5) . . ?
C6 C7 C2 123.6(6) . . ?
C6 C7 O8 115.3(5) . . ?
C2 C7 O8 121.1(5) . . ?
C12 C1 C2 113.9(5) . . ?
C12 C1 S11 110.1(4) . . ?
C2 C1 S11 110.5(4) . . ?
O18 C9 O8 117.6(6) . . ?
O18 C9 C10 126.2(6) . . ?
O8 C9 C10 116.2(5) . . ?
C17 C12 C13 117.4(7) . . ?
C17 C12 C1 123.4(6) . . ?
C13 C12 C1 119.1(6) . . ?
C2 C3 C4 121.1(6) . . ?
C7 C6 C5 118.0(6) . . ?
C4 C5 C6 120.9(6) . . ?
C9 C10 S11 112.2(5) . . ?
C12 C17 C16 123.0(8) . . ?
C5 C4 C3 119.6(6) . . ?
C14 C13 C12 120.4(8) . . ?
C17 C16 C15 117.9(8) . . ?
C14 C15 C16 119.9(8) . . ?
C15 C14 C13 121.4(9) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_ortho1_a
_database_code_depnum_ccdc_archive 'CCDC 1984977'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;Co editor of Acta Crystallographica E
India
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        P21212
_chemical_formula_moiety         'C17 H16 O4 S'
_chemical_formula_sum            'C17 H16 O4 S'
_chemical_formula_weight         316.36
_chemical_absolute_configuration syn
_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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   7.969(3)
_cell_length_b                   34.663(14)
_cell_length_c                   5.361(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1480.9(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    690
_cell_measurement_temperature    100
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1029 before and 0.0844 after correction.
The Ratio of minimum to maximum transmission is 0.7717.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_preparation       Synthesis
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1470
_diffrn_reflns_av_unetI/netI     0.1607
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12986
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.697
_diffrn_reflns_theta_min         4.582
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                2003
_reflns_number_total             3818
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0762
_refine_ls_restrained_S_all      0.959
_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)+(0.0796P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1915
_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. Others
 Sof(O4B)=Sof(C16B)=Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=1-FVAR(1)
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(O4A)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C16A(H16A,H16B), C16B(H16C,H16D)
3.b Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C17B(H17D,H17E,H17F)
;
_atom_sites_solution_hydrogens   mixed
_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 0.19950(18) 0.63056(5) 1.0787(4) 0.0339(4) Uani 1 1 d . . . . .
O1 O 0.2847(5) 0.57861(12) 0.5400(10) 0.0376(12) Uani 1 1 d . . . . .
O2 O 0.0174(5) 0.63621(14) 1.1195(11) 0.0502(14) Uani 1 1 d . . . . .
O3 O 0.0514(6) 0.55330(14) 0.6789(12) 0.0579(17) Uani 1 1 d . . . . .
C8 C 0.4214(6) 0.63593(17) 0.6991(12) 0.0256(14) Uani 1 1 d . . . . .
C4 C 0.1406(7) 0.75279(19) 0.5733(16) 0.0352(16) Uani 1 1 d . . . . .
H4 H 0.082(8) 0.7652(18) 0.420(15) 0.042 Uiso 1 1 d R . . . .
C2 C 0.2350(6) 0.69439(17) 0.7787(13) 0.0275(14) Uani 1 1 d . . . . .
C3 C 0.1482(7) 0.71285(19) 0.5883(15) 0.0302(15) Uani 1 1 d . . . . .
H3 H 0.109(8) 0.7006(18) 0.448(15) 0.036 Uiso 1 1 d R . . . .
C15 C 0.2316(8) 0.58001(19) 0.9899(15) 0.0382(19) Uani 1 1 d . . . . .
H15A H 0.364(11) 0.575(2) 1.018(17) 0.08(3) Uiso 1 1 d . . . . .
H15B H 0.161(9) 0.567(2) 1.115(16) 0.05(2) Uiso 1 1 d . . . . .
C9 C 0.5710(7) 0.65597(19) 0.7387(14) 0.0326(16) Uani 1 1 d . . . . .
H9 H 0.564(8) 0.6820(19) 0.826(14) 0.039 Uiso 1 1 d R . . . .
C1 C 0.2505(7) 0.65123(18) 0.7738(14) 0.0297(16) Uani 1 1 d . . . . .
C13 C 0.4305(7) 0.60017(17) 0.5864(15) 0.0326(15) Uani 1 1 d . . . . .
C5 C 0.2185(8) 0.7748(2) 0.7555(16) 0.0389(18) Uani 1 1 d . . . . .
H5 H 0.215(8) 0.803(2) 0.746(15) 0.047 Uiso 1 1 d R . . . .
C14 C 0.1805(8) 0.56928(18) 0.7365(17) 0.0403(19) Uani 1 1 d . . . . .
C10 C 0.7214(8) 0.6406(2) 0.6606(15) 0.0396(18) Uani 1 1 d . . . . .
H10 H 0.833(8) 0.6548(19) 0.707(16) 0.048 Uiso 1 1 d R . . . .
C7 C 0.3096(7) 0.71700(18) 0.9657(14) 0.0326(16) Uani 1 1 d . . . . .
H7 H 0.364(7) 0.7071(18) 1.150(14) 0.039 Uiso 1 1 d R . . . .
C6 C 0.3043(8) 0.75722(19) 0.9485(16) 0.0378(16) Uani 1 1 d . . . . .
H6 H 0.355(8) 0.7720(19) 1.086(16) 0.045 Uiso 1 1 d R . . . .
C12 C 0.5790(8) 0.5852(2) 0.4941(15) 0.048(2) Uani 1 1 d . . . . .
C11 C 0.7268(8) 0.6062(2) 0.5270(15) 0.048(2) Uani 1 1 d . . . . .
H11 H 0.847(9) 0.597(2) 0.465(16) 0.057 Uiso 1 1 d R . . . .
C16A C 0.6972(16) 0.5232(4) 0.342(3) 0.036(5) Uani 0.50(2) 1 d . . P A 1
H16A H 0.673545 0.495179 0.347709 0.044 Uiso 0.50(2) 1 calc R . P A 1
H16B H 0.789432 0.528651 0.460921 0.044 Uiso 0.50(2) 1 calc R . P A 1
C17A C 0.750(2) 0.5342(6) 0.086(5) 0.043(5) Uani 0.50(2) 1 d . . P A 1
H17A H 0.655620 0.531091 -0.028653 0.065 Uiso 0.50(2) 1 calc GR . P A 1
H17B H 0.843141 0.517600 0.033007 0.065 Uiso 0.50(2) 1 calc GR . P A 1
H17C H 0.787103 0.561181 0.085627 0.065 Uiso 0.50(2) 1 calc GR . P A 1
O4A O 0.5477(14) 0.5445(4) 0.417(3) 0.037(4) Uani 0.50(2) 1 d . . P A 1
O4B O 0.5865(15) 0.5589(4) 0.322(3) 0.036(4) Uani 0.50(2) 1 d . . P A 2
C16B C 0.740(2) 0.5500(5) 0.177(4) 0.032(4) Uani 0.50(2) 1 d . . P A 2
H16C H 0.831636 0.541869 0.289984 0.039 Uiso 0.50(2) 1 calc R . P A 2
H16D H 0.777028 0.572823 0.081435 0.039 Uiso 0.50(2) 1 calc R . P A 2
C17B C 0.692(2) 0.5178(5) 0.006(4) 0.048(5) Uani 0.50(2) 1 d . . P A 2
H17D H 0.599724 0.526264 -0.102503 0.072 Uiso 0.50(2) 1 calc GR . P A 2
H17E H 0.655715 0.495484 0.103837 0.072 Uiso 0.50(2) 1 calc GR . P A 2
H17F H 0.788743 0.510694 -0.097004 0.072 Uiso 0.50(2) 1 calc GR . P A 2
H1 H 0.161(9) 0.639(2) 0.649(18) 0.07(3) Uiso 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 O2 1.481(4) . ?
S1 C15 1.834(7) . ?
S1 C1 1.830(7) . ?
O1 C13 1.403(7) . ?
O1 C14 1.380(9) . ?
O3 C14 1.208(7) . ?
C8 C9 1.397(8) . ?
C8 C1 1.515(8) . ?
C8 C13 1.381(9) . ?
C4 H4 1.04(8) . ?
C4 C3 1.388(9) . ?
C4 C5 1.386(11) . ?
C2 C3 1.389(9) . ?
C2 C1 1.501(9) . ?
C2 C7 1.404(9) . ?
C3 H3 0.92(8) . ?
C15 H15A 1.08(9) . ?
C15 H15B 0.98(8) . ?
C15 C14 1.466(11) . ?
C9 H9 1.02(7) . ?
C9 C10 1.377(9) . ?
C1 H1 1.07(8) . ?
C13 C12 1.383(9) . ?
C5 H5 0.98(7) . ?
C5 C6 1.381(11) . ?
C10 H10 1.05(7) . ?
C10 C11 1.392(10) . ?
C7 H7 1.13(8) . ?
C7 C6 1.398(9) . ?
C6 H6 0.98(8) . ?
C12 C11 1.396(10) . ?
C12 O4A 1.491(14) . ?
C12 O4B 1.299(13) . ?
C11 H11 1.07(7) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A C17A 1.49(3) . ?
C16A O4A 1.458(16) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
O4B C16B 1.48(2) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C16B C17B 1.50(3) . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 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
O2 S1 C15 107.6(3) . . ?
O2 S1 C1 107.3(3) . . ?
C1 S1 C15 96.4(3) . . ?
C14 O1 C13 119.2(6) . . ?
C9 C8 C1 123.6(6) . . ?
C13 C8 C9 117.9(5) . . ?
C13 C8 C1 118.5(5) . . ?
C3 C4 H4 119(4) . . ?
C5 C4 H4 122(4) . . ?
C5 C4 C3 119.2(7) . . ?
C3 C2 C1 119.1(6) . . ?
C3 C2 C7 118.6(6) . . ?
C7 C2 C1 122.3(6) . . ?
C4 C3 C2 121.6(7) . . ?
C4 C3 H3 113(4) . . ?
C2 C3 H3 124(4) . . ?
S1 C15 H15A 104(4) . . ?
S1 C15 H15B 100(4) . . ?
H15A C15 H15B 113(6) . . ?
C14 C15 S1 116.4(5) . . ?
C14 C15 H15A 111(5) . . ?
C14 C15 H15B 111(5) . . ?
C8 C9 H9 118(4) . . ?
C10 C9 C8 120.3(6) . . ?
C10 C9 H9 122(4) . . ?
S1 C1 H1 104(5) . . ?
C8 C1 S1 107.4(4) . . ?
C8 C1 H1 107(4) . . ?
C2 C1 S1 110.9(5) . . ?
C2 C1 C8 115.3(5) . . ?
C2 C1 H1 111(4) . . ?
C8 C13 O1 120.8(5) . . ?
C8 C13 C12 122.5(5) . . ?
C12 C13 O1 116.4(6) . . ?
C4 C5 H5 120(5) . . ?
C6 C5 C4 120.5(7) . . ?
C6 C5 H5 120(5) . . ?
O1 C14 C15 118.7(5) . . ?
O3 C14 O1 115.2(7) . . ?
O3 C14 C15 126.1(8) . . ?
C9 C10 H10 119(4) . . ?
C9 C10 C11 121.0(6) . . ?
C11 C10 H10 120(4) . . ?
C2 C7 H7 128(3) . . ?
C6 C7 C2 119.8(7) . . ?
C6 C7 H7 112(3) . . ?
C5 C6 C7 120.2(7) . . ?
C5 C6 H6 122(4) . . ?
C7 C6 H6 117(4) . . ?
C13 C12 C11 118.8(6) . . ?
C13 C12 O4A 108.1(7) . . ?
C11 C12 O4A 132.0(7) . . ?
O4B C12 C13 123.8(8) . . ?
O4B C12 C11 114.6(8) . . ?
C10 C11 C12 119.0(6) . . ?
C10 C11 H11 117(4) . . ?
C12 C11 H11 124(4) . . ?
H16A C16A H16B 108.0 . . ?
C17A C16A H16A 109.5 . . ?
C17A C16A H16B 109.5 . . ?
O4A C16A H16A 109.5 . . ?
O4A C16A H16B 109.5 . . ?
O4A C16A C17A 110.9(15) . . ?
C16A C17A H17A 109.5 . . ?
C16A C17A H17B 109.5 . . ?
C16A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C16A O4A C12 114.7(10) . . ?
C12 O4B C16B 123.9(12) . . ?
O4B C16B H16C 110.6 . . ?
O4B C16B H16D 110.6 . . ?
O4B C16B C17B 105.5(12) . . ?
H16C C16B H16D 108.8 . . ?
C17B C16B H16C 110.6 . . ?
C17B C16B H16D 110.6 . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C15 C14 O1 78.6(7) . . . . ?
S1 C15 C14 O3 -99.8(7) . . . . ?
O1 C13 C12 C11 177.7(7) . . . . ?
O1 C13 C12 O4A -13.0(11) . . . . ?
O1 C13 C12 O4B 17.6(14) . . . . ?
O2 S1 C15 C14 74.0(6) . . . . ?
O2 S1 C1 C8 -164.3(4) . . . . ?
O2 S1 C1 C2 68.9(5) . . . . ?
C8 C9 C10 C11 4.2(11) . . . . ?
C8 C13 C12 C11 3.2(12) . . . . ?
C8 C13 C12 O4A 172.6(9) . . . . ?
C8 C13 C12 O4B -156.8(11) . . . . ?
C4 C5 C6 C7 -1.8(10) . . . . ?
C2 C7 C6 C5 3.5(10) . . . . ?
C3 C4 C5 C6 0.7(10) . . . . ?
C3 C2 C1 S1 -132.6(5) . . . . ?
C3 C2 C1 C8 105.1(7) . . . . ?
C3 C2 C7 C6 -4.0(9) . . . . ?
C15 S1 C1 C8 -53.7(5) . . . . ?
C15 S1 C1 C2 179.6(4) . . . . ?
C9 C8 C1 S1 -96.0(6) . . . . ?
C9 C8 C1 C2 28.1(9) . . . . ?
C9 C8 C13 O1 -179.7(6) . . . . ?
C9 C8 C13 C12 -5.5(11) . . . . ?
C9 C10 C11 C12 -6.4(12) . . . . ?
C1 S1 C15 C14 -36.5(6) . . . . ?
C1 C8 C9 C10 -178.5(7) . . . . ?
C1 C8 C13 O1 0.6(10) . . . . ?
C1 C8 C13 C12 174.8(7) . . . . ?
C1 C2 C3 C4 -175.1(6) . . . . ?
C1 C2 C7 C6 174.1(6) . . . . ?
C13 O1 C14 O3 174.5(5) . . . . ?
C13 O1 C14 C15 -4.1(8) . . . . ?
C13 C8 C9 C10 1.7(10) . . . . ?
C13 C8 C1 S1 83.7(7) . . . . ?
C13 C8 C1 C2 -152.1(7) . . . . ?
C13 C12 C11 C10 2.7(12) . . . . ?
C13 C12 O4A C16A -173.2(12) . . . . ?
C13 C12 O4B C16B 163.7(13) . . . . ?
C5 C4 C3 C2 -1.4(9) . . . . ?
C14 O1 C13 C8 -57.3(8) . . . . ?
C14 O1 C13 C12 128.2(7) . . . . ?
C7 C2 C3 C4 3.0(9) . . . . ?
C7 C2 C1 S1 49.3(7) . . . . ?
C7 C2 C1 C8 -72.9(8) . . . . ?
C12 O4B C16B C17B 179.0(15) . . . . ?
C11 C12 O4A C16A -6(2) . . . . ?
C11 C12 O4B C16B 2.9(19) . . . . ?
C17A C16A O4A C12 -77.4(18) . . . . ?
O4A C12 C11 C10 -163.6(12) . . . . ?
O4B C12 C11 C10 164.6(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
