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

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

data_sm-46_a
_audit_block_doi                 10.5517/ccdc.csd.cc2g1rr1
_database_code_depnum_ccdc_archive 'CCDC 2265813'
loop_
_audit_author_name
_audit_author_address
'Pavan K. Kancharla'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-05-27 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 O4'
_chemical_formula_weight         374.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2137(5)
_cell_length_b                   6.6371(5)
_cell_length_c                   20.4802(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.575(2)
_cell_angle_gamma                90
_cell_volume                     975.91(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.48

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20013
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3416
_reflns_number_gt                3141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+0.7053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3416
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1882
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.132
_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_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 0.2213(6) 0.2731(7) 0.3525(2) 0.0540(11) Uani 1 1 d . . . . .
O2 O 0.2721(5) 0.6040(6) 0.3662(2) 0.0477(10) Uani 1 1 d . . . . .
O4 O 0.4956(7) 0.4421(8) 0.07577(18) 0.0631(13) Uani 1 1 d . . . . .
O1 O 0.0245(8) 0.9078(9) 0.0749(2) 0.0704(14) Uani 1 1 d . . . . .
C8 C 0.3188(7) 0.4108(8) 0.3718(2) 0.0339(11) Uani 1 1 d . . . . .
C14 C 0.6327(6) 0.2425(7) 0.3886(2) 0.0295(10) Uani 1 1 d . . . . .
C13 C 0.8045(7) 0.2228(9) 0.4258(3) 0.0393(12) Uani 1 1 d . . . . .
H13 H 0.889581 0.127974 0.413612 0.047 Uiso 1 1 calc R U . . .
C20 C 0.5242(8) 0.3708(9) 0.1387(2) 0.0407(13) Uani 1 1 d . . . . .
C9 C 0.5084(6) 0.3869(7) 0.4074(2) 0.0297(10) Uani 1 1 d . . . . .
C11 C 0.7248(8) 0.4814(9) 0.4999(2) 0.0423(13) Uani 1 1 d . . . . .
H11 H 0.753833 0.558636 0.537372 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5555(7) 0.5048(8) 0.4628(2) 0.0366(11) Uani 1 1 d . . . . .
H10 H 0.471691 0.600958 0.474983 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5907(6) 0.1075(8) 0.3306(2) 0.0317(11) Uani 1 1 d . . . . .
C17 C 0.5625(6) 0.2014(7) 0.2643(2) 0.0308(11) Uani 1 1 d . . . . .
C21 C 0.6260(8) 0.4713(9) 0.1896(3) 0.0422(13) Uani 1 1 d . . . . .
H21 H 0.682463 0.594248 0.182430 0.051 Uiso 1 1 calc R U . . .
C3 C -0.0034(7) 0.9071(10) 0.2527(3) 0.0439(13) Uani 1 1 d . . . . .
H3 H -0.041352 0.989937 0.285555 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1141(9) 0.6691(10) 0.1562(3) 0.0490(15) Uani 1 1 d . . . . .
H6 H 0.154117 0.588483 0.123151 0.059 Uiso 1 1 calc R U . . .
C19 C 0.4420(8) 0.1906(9) 0.1507(3) 0.0464(15) Uani 1 1 d . . . . .
H19 H 0.373559 0.123386 0.116594 0.056 Uiso 1 1 calc R U . . .
C18 C 0.4587(8) 0.1069(9) 0.2126(3) 0.0419(13) Uani 1 1 d . . . . .
H18 H 0.399639 -0.014513 0.219688 0.050 Uiso 1 1 calc R U . . .
C22 C 0.6417(7) 0.3848(8) 0.2514(2) 0.0353(12) Uani 1 1 d . . . . .
H22 H 0.708471 0.453116 0.285741 0.042 Uiso 1 1 calc R U . . .
C12 C 0.8503(8) 0.3412(9) 0.4803(3) 0.0434(13) Uani 1 1 d . . . . .
H12 H 0.966109 0.326858 0.504045 0.052 Uiso 1 1 calc R U . . .
C16 C 0.5917(9) -0.0907(9) 0.3394(3) 0.0522(15) Uani 1 1 d . . . . .
H16A H 0.574412 -0.176423 0.303375 0.063 Uiso 1 1 calc R U . . .
H16B H 0.609708 -0.143830 0.381534 0.063 Uiso 1 1 calc R U . . .
C4 C 0.0736(7) 0.7221(10) 0.2699(3) 0.0418(13) Uani 1 1 d . . . . .
C5 C 0.1347(8) 0.6027(10) 0.2203(3) 0.0462(13) Uani 1 1 d . . . . .
H5 H 0.189389 0.478219 0.230461 0.055 Uiso 1 1 calc R U . . .
C2 C -0.0261(8) 0.9739(10) 0.1884(3) 0.0496(14) Uani 1 1 d . . . . .
H2 H -0.081520 1.097843 0.178120 0.060 Uiso 1 1 calc R U . . .
C1 C 0.0339(8) 0.8557(10) 0.1404(3) 0.0484(15) Uani 1 1 d . . . . .
C7 C 0.0822(8) 0.6494(11) 0.3391(3) 0.0539(16) Uani 1 1 d . . . . .
H7A H 0.030371 0.751600 0.365859 0.065 Uiso 1 1 calc R U . . .
H7B H 0.006449 0.529057 0.340724 0.065 Uiso 1 1 calc R U . . .
C23 C 0.5802(16) 0.6323(15) 0.0620(4) 0.095(3) Uani 1 1 d . . . . .
H23A H 0.528291 0.736706 0.087107 0.143 Uiso 1 1 calc R U . . .
H23B H 0.556536 0.662132 0.016121 0.143 Uiso 1 1 calc R U . . .
H23C H 0.712159 0.624664 0.073748 0.143 Uiso 1 1 calc R U . . .
C24 C -0.0703(16) 1.0887(15) 0.0560(4) 0.095(3) Uani 1 1 d . . . . .
H24A H -0.196939 1.080102 0.066414 0.143 Uiso 1 1 calc R U . . .
H24B H -0.068325 1.108600 0.009650 0.143 Uiso 1 1 calc R U . . .
H24C H -0.009723 1.200070 0.079172 0.143 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 1.197(6) . ?
O2 C8 1.328(7) . ?
O2 C7 1.459(7) . ?
O4 C20 1.369(6) . ?
O4 C23 1.442(10) . ?
O1 C1 1.381(7) . ?
O1 C24 1.417(10) . ?
C8 C9 1.494(7) . ?
C14 C9 1.391(7) . ?
C14 C13 1.396(7) . ?
C14 C15 1.496(7) . ?
C13 C12 1.379(8) . ?
C13 H13 0.9300 . ?
C20 C19 1.368(9) . ?
C20 C21 1.388(8) . ?
C9 C10 1.393(7) . ?
C11 C10 1.383(8) . ?
C11 C12 1.384(8) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C15 C16 1.328(8) . ?
C15 C17 1.489(7) . ?
C17 C22 1.381(7) . ?
C17 C18 1.387(7) . ?
C21 C22 1.385(7) . ?
C21 H21 0.9300 . ?
C3 C4 1.378(9) . ?
C3 C2 1.385(8) . ?
C3 H3 0.9300 . ?
C6 C5 1.381(9) . ?
C6 C1 1.391(9) . ?
C6 H6 0.9300 . ?
C19 C18 1.377(8) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C22 H22 0.9300 . ?
C12 H12 0.9300 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C4 C5 1.393(8) . ?
C4 C7 1.492(8) . ?
C5 H5 0.9300 . ?
C2 C1 1.360(9) . ?
C2 H2 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C7 117.0(5) . . ?
C20 O4 C23 117.3(5) . . ?
C1 O1 C24 117.0(6) . . ?
O3 C8 O2 124.9(5) . . ?
O3 C8 C9 124.1(5) . . ?
O2 C8 C9 110.9(4) . . ?
C9 C14 C13 118.4(4) . . ?
C9 C14 C15 123.0(4) . . ?
C13 C14 C15 118.6(4) . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C19 C20 O4 116.4(5) . . ?
C19 C20 C21 119.4(5) . . ?
O4 C20 C21 124.2(5) . . ?
C14 C9 C10 119.9(4) . . ?
C14 C9 C8 121.5(4) . . ?
C10 C9 C8 118.4(4) . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C10 C9 121.1(5) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C16 C15 C17 122.5(5) . . ?
C16 C15 C14 119.2(5) . . ?
C17 C15 C14 118.2(4) . . ?
C22 C17 C18 117.1(5) . . ?
C22 C17 C15 121.4(4) . . ?
C18 C17 C15 121.5(5) . . ?
C22 C21 C20 118.6(5) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C4 C3 C2 122.3(5) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C5 C6 C1 120.6(6) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C20 C19 C18 121.2(5) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C18 C17 120.9(5) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C17 C22 C21 122.8(5) . . ?
C17 C22 H22 118.6 . . ?
C21 C22 H22 118.6 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C3 C4 C5 118.0(5) . . ?
C3 C4 C7 120.6(5) . . ?
C5 C4 C7 121.4(6) . . ?
C6 C5 C4 119.9(6) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C2 C3 119.1(6) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C1 O1 124.7(6) . . ?
C2 C1 C6 120.0(6) . . ?
O1 C1 C6 115.3(5) . . ?
O2 C7 C4 112.3(5) . . ?
O2 C7 H7A 109.1 . . ?
C4 C7 H7A 109.1 . . ?
O2 C7 H7B 109.1 . . ?
C4 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C7 O2 C8 O3 5.1(8) . . . . ?
C7 O2 C8 C9 -173.3(4) . . . . ?
C9 C14 C13 C12 0.7(8) . . . . ?
C15 C14 C13 C12 -179.2(5) . . . . ?
C23 O4 C20 C19 179.7(7) . . . . ?
C23 O4 C20 C21 1.2(9) . . . . ?
C13 C14 C9 C10 -1.1(7) . . . . ?
C15 C14 C9 C10 178.8(4) . . . . ?
C13 C14 C9 C8 -177.2(4) . . . . ?
C15 C14 C9 C8 2.6(7) . . . . ?
O3 C8 C9 C14 40.5(7) . . . . ?
O2 C8 C9 C14 -141.0(5) . . . . ?
O3 C8 C9 C10 -135.6(5) . . . . ?
O2 C8 C9 C10 42.8(6) . . . . ?
C12 C11 C10 C9 1.5(8) . . . . ?
C14 C9 C10 C11 0.0(7) . . . . ?
C8 C9 C10 C11 176.3(5) . . . . ?
C9 C14 C15 C16 -120.7(6) . . . . ?
C13 C14 C15 C16 59.2(7) . . . . ?
C9 C14 C15 C17 63.6(6) . . . . ?
C13 C14 C15 C17 -116.5(5) . . . . ?
C16 C15 C17 C22 -149.8(6) . . . . ?
C14 C15 C17 C22 25.7(6) . . . . ?
C16 C15 C17 C18 28.9(8) . . . . ?
C14 C15 C17 C18 -155.6(5) . . . . ?
C19 C20 C21 C22 0.3(8) . . . . ?
O4 C20 C21 C22 178.8(5) . . . . ?
O4 C20 C19 C18 -178.7(5) . . . . ?
C21 C20 C19 C18 -0.2(9) . . . . ?
C20 C19 C18 C17 -1.2(9) . . . . ?
C22 C17 C18 C19 2.2(8) . . . . ?
C15 C17 C18 C19 -176.6(5) . . . . ?
C18 C17 C22 C21 -2.1(8) . . . . ?
C15 C17 C22 C21 176.7(5) . . . . ?
C20 C21 C22 C17 0.9(8) . . . . ?
C14 C13 C12 C11 0.9(9) . . . . ?
C10 C11 C12 C13 -2.0(9) . . . . ?
C2 C3 C4 C5 1.9(8) . . . . ?
C2 C3 C4 C7 -175.3(6) . . . . ?
C1 C6 C5 C4 0.5(9) . . . . ?
C3 C4 C5 C6 -1.2(8) . . . . ?
C7 C4 C5 C6 175.9(6) . . . . ?
C4 C3 C2 C1 -1.8(9) . . . . ?
C3 C2 C1 O1 -177.9(6) . . . . ?
C3 C2 C1 C6 1.0(9) . . . . ?
C24 O1 C1 C2 -6.2(10) . . . . ?
C24 O1 C1 C6 174.8(7) . . . . ?
C5 C6 C1 C2 -0.4(9) . . . . ?
C5 C6 C1 O1 178.6(6) . . . . ?
C8 O2 C7 C4 -104.7(6) . . . . ?
C3 C4 C7 O2 -122.5(6) . . . . ?
C5 C4 C7 O2 60.5(8) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_sm76a
_audit_block_doi                 10.5517/ccdc.csd.cc2g1rs2
_database_code_depnum_ccdc_archive 'CCDC 2265814'
loop_
_audit_author_name
_audit_author_address
'Pavan K. Kancharla'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-05-27 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 O3 S'
_chemical_formula_weight         348.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5684(18)
_cell_length_b                   10.8101(19)
_cell_length_c                   13.734(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.963(15)
_cell_angle_gamma                90
_cell_volume                     1861.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    738
_cell_measurement_theta_min      2.8310
_cell_measurement_theta_max      22.0800

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.06960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6503
_diffrn_reflns_av_unetI/netI     0.2383
_diffrn_reflns_av_R_equivalents  0.1325
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.400
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3250
_reflns_number_gt                1116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.6740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3250
_refine_ls_number_parameters     220
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2251
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2251
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.942
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.67410(13) 0.74395(17) 0.50079(13) 0.0875(8) Uani 1 1 d . . . . .
O002 O 0.2530(3) 0.7704(3) 0.2030(2) 0.0472(10) Uani 1 1 d . . . . .
O003 O 0.4163(3) 0.6214(3) 0.1743(2) 0.0592(11) Uani 1 1 d . . . . .
O004 O 0.2209(3) 0.8616(3) 0.3805(3) 0.0581(11) Uani 1 1 d . . . . .
C005 C 0.3252(4) 0.7446(4) 0.2812(3) 0.0388(13) Uani 1 1 d . . . . .
C006 C 0.3118(4) 0.7914(4) 0.3735(4) 0.0385(13) Uani 1 1 d . . . . .
C007 C 0.3841(4) 0.7637(5) 0.4508(4) 0.0437(14) Uani 1 1 d . . . . .
H007 H 0.374140 0.794957 0.512589 0.052 Uiso 1 1 calc R U . . .
C008 C 0.4119(4) 0.6680(5) 0.2669(3) 0.0422(13) Uani 1 1 d . . . . .
C009 C 0.4714(4) 0.6896(4) 0.4363(4) 0.0420(13) Uani 1 1 d . . . . .
C00A C 0.4845(4) 0.6402(4) 0.3445(3) 0.0421(14) Uani 1 1 d . . . . .
H00A H 0.541964 0.588508 0.335106 0.050 Uiso 1 1 calc R U . . .
C00B C 0.7704(4) 0.6901(5) 0.5967(4) 0.0473(14) Uani 1 1 d . . . . .
C00C C 0.5514(4) 0.6633(5) 0.5203(4) 0.0515(15) Uani 1 1 d . . . . .
H00B H 0.564718 0.575000 0.525054 0.062 Uiso 1 1 calc R U . . .
H00C H 0.523768 0.690693 0.580924 0.062 Uiso 1 1 calc R U . . .
C00D C 0.2658(4) 0.8900(5) 0.1616(4) 0.0582(16) Uani 1 1 d . . . . .
H00D H 0.217871 0.898730 0.104520 0.087 Uiso 1 1 calc R U . . .
H00E H 0.337906 0.899613 0.144048 0.087 Uiso 1 1 calc R U . . .
H00F H 0.250152 0.952116 0.208520 0.087 Uiso 1 1 calc R U . . .
C00E C 0.4868(4) 0.5221(5) 0.1602(4) 0.0625(17) Uani 1 1 d . . . . .
H00G H 0.473331 0.489469 0.095532 0.094 Uiso 1 1 calc R U . . .
H00H H 0.475966 0.458313 0.207155 0.094 Uiso 1 1 calc R U . . .
H00I H 0.559094 0.551082 0.168389 0.094 Uiso 1 1 calc R U . . .
C00F C 0.1930(5) 0.8964(6) 0.4753(4) 0.081(2) Uani 1 1 d . . . . .
H00J H 0.123665 0.933951 0.470790 0.122 Uiso 1 1 calc R U . . .
H00K H 0.244501 0.954353 0.502964 0.122 Uiso 1 1 calc R U . . .
H00L H 0.192141 0.824320 0.516049 0.122 Uiso 1 1 calc R U . . .
C00G C 0.7859(5) 0.5534(6) 0.5953(5) 0.097(2) Uani 1 1 d . . . . .
H00M H 0.806650 0.527992 0.531607 0.116 Uiso 1 1 calc R U . . .
H00N H 0.719338 0.512420 0.607183 0.116 Uiso 1 1 calc R U . . .
C00H C 0.9644(6) 0.7115(10) 0.6549(7) 0.110(4) Uani 1 1 d . . . . .
H00O H 1.032059 0.751190 0.641934 0.132 Uiso 1 1 calc R U . . .
C00I C 0.8727(8) 0.5147(7) 0.6742(9) 0.121(4) Uani 1 1 d D . . . .
H00P H 0.881147 0.424571 0.673747 0.145 Uiso 1 1 calc R U . . .
C00J C 0.9762(6) 0.5750(10) 0.6552(6) 0.114(3) Uani 1 1 d . . . . .
H00Q H 1.030355 0.550715 0.705239 0.137 Uiso 1 1 calc R U . . .
H00R H 0.998863 0.547719 0.592570 0.137 Uiso 1 1 calc R U . . .
C00K C 0.8279(8) 0.6890(13) 0.7723(6) 0.134(5) Uani 1 1 d D . . . .
H00S H 0.806599 0.713477 0.836858 0.161 Uiso 1 1 calc R U . . .
C00L C 0.7394(5) 0.7258(8) 0.6953(5) 0.110(3) Uani 1 1 d . . . . .
H00T H 0.673460 0.684753 0.708873 0.132 Uiso 1 1 calc R U . . .
H00U H 0.727758 0.814447 0.697676 0.132 Uiso 1 1 calc R U . . .
C00M C 0.9311(8) 0.7482(8) 0.7553(9) 0.138(4) Uani 1 1 d . . . . .
H00V H 0.984946 0.722039 0.804980 0.166 Uiso 1 1 calc R U . . .
H00W H 0.924157 0.837457 0.759057 0.166 Uiso 1 1 calc R U . . .
C00N C 0.8762(5) 0.7509(8) 0.5780(7) 0.149(4) Uani 1 1 d . . . . .
H00X H 0.868114 0.840095 0.579491 0.179 Uiso 1 1 calc R U . . .
H00Y H 0.896573 0.727840 0.513618 0.179 Uiso 1 1 calc R U . . .
C00O C 0.8434(8) 0.5555(14) 0.7710(8) 0.169(6) Uani 1 1 d D . . . .
H00Z H 0.778214 0.514501 0.786959 0.203 Uiso 1 1 calc R U . . .
H H 0.899346 0.532743 0.819935 0.203 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
S001 C00C 1.808(5) . ?
S001 C00B 1.822(5) . ?
O002 C005 1.386(5) . ?
O002 C00D 1.426(5) . ?
O003 C008 1.372(5) . ?
O003 C00E 1.415(5) . ?
O004 C006 1.380(5) . ?
O004 C00F 1.422(6) . ?
C005 C006 1.387(6) . ?
C005 C008 1.393(6) . ?
C006 C007 1.381(6) . ?
C007 C009 1.384(7) . ?
C007 H007 0.9300 . ?
C008 C00A 1.387(6) . ?
C009 C00A 1.388(6) . ?
C009 C00C 1.505(6) . ?
C00A H00A 0.9300 . ?
C00B C00L 1.485(8) . ?
C00B C00G 1.491(7) . ?
C00B C00N 1.521(7) . ?
C00C H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00D H00D 0.9600 . ?
C00D H00E 0.9600 . ?
C00D H00F 0.9600 . ?
C00E H00G 0.9600 . ?
C00E H00H 0.9600 . ?
C00E H00I 0.9600 . ?
C00F H00J 0.9600 . ?
C00F H00K 0.9600 . ?
C00F H00L 0.9600 . ?
C00G C00I 1.541(8) . ?
C00G H00M 0.9700 . ?
C00G H00N 0.9700 . ?
C00H C00J 1.484(10) . ?
C00H C00M 1.520(11) . ?
C00H C00N 1.537(9) . ?
C00H H00O 0.9800 . ?
C00I C00O 1.473(10) . ?
C00I C00J 1.493(11) . ?
C00I H00P 0.9800 . ?
C00J H00Q 0.9700 . ?
C00J H00R 0.9700 . ?
C00K C00O 1.456(11) . ?
C00K C00M 1.479(12) . ?
C00K C00L 1.533(9) . ?
C00K H00S 0.9800 . ?
C00L H00T 0.9700 . ?
C00L H00U 0.9700 . ?
C00M H00V 0.9700 . ?
C00M H00W 0.9700 . ?
C00N H00X 0.9700 . ?
C00N H00Y 0.9700 . ?
C00O H00Z 0.9700 . ?
C00O H 0.9700 . ?

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
C00C S001 C00B 105.6(2) . . ?
C005 O002 C00D 113.9(4) . . ?
C008 O003 C00E 118.1(4) . . ?
C006 O004 C00F 117.8(4) . . ?
O002 C005 C006 121.4(4) . . ?
O002 C005 C008 119.2(4) . . ?
C006 C005 C008 119.5(5) . . ?
O004 C006 C007 124.8(4) . . ?
O004 C006 C005 114.7(4) . . ?
C007 C006 C005 120.5(5) . . ?
C006 C007 C009 120.1(5) . . ?
C006 C007 H007 120.0 . . ?
C009 C007 H007 120.0 . . ?
O003 C008 C00A 124.5(5) . . ?
O003 C008 C005 115.5(4) . . ?
C00A C008 C005 120.0(5) . . ?
C007 C009 C00A 119.9(5) . . ?
C007 C009 C00C 119.6(5) . . ?
C00A C009 C00C 120.6(5) . . ?
C008 C00A C009 120.1(5) . . ?
C008 C00A H00A 119.9 . . ?
C009 C00A H00A 119.9 . . ?
C00L C00B C00G 108.2(5) . . ?
C00L C00B C00N 109.2(6) . . ?
C00G C00B C00N 108.0(6) . . ?
C00L C00B S001 111.9(4) . . ?
C00G C00B S001 112.9(4) . . ?
C00N C00B S001 106.5(4) . . ?
C009 C00C S001 109.1(3) . . ?
C009 C00C H00B 109.9 . . ?
S001 C00C H00B 109.9 . . ?
C009 C00C H00C 109.9 . . ?
S001 C00C H00C 109.9 . . ?
H00B C00C H00C 108.3 . . ?
O002 C00D H00D 109.5 . . ?
O002 C00D H00E 109.5 . . ?
H00D C00D H00E 109.5 . . ?
O002 C00D H00F 109.5 . . ?
H00D C00D H00F 109.5 . . ?
H00E C00D H00F 109.5 . . ?
O003 C00E H00G 109.5 . . ?
O003 C00E H00H 109.5 . . ?
H00G C00E H00H 109.5 . . ?
O003 C00E H00I 109.5 . . ?
H00G C00E H00I 109.5 . . ?
H00H C00E H00I 109.5 . . ?
O004 C00F H00J 109.5 . . ?
O004 C00F H00K 109.5 . . ?
H00J C00F H00K 109.5 . . ?
O004 C00F H00L 109.5 . . ?
H00J C00F H00L 109.5 . . ?
H00K C00F H00L 109.5 . . ?
C00B C00G C00I 110.3(5) . . ?
C00B C00G H00M 109.6 . . ?
C00I C00G H00M 109.6 . . ?
C00B C00G H00N 109.6 . . ?
C00I C00G H00N 109.6 . . ?
H00M C00G H00N 108.1 . . ?
C00J C00H C00M 106.9(7) . . ?
C00J C00H C00N 110.1(8) . . ?
C00M C00H C00N 108.7(8) . . ?
C00J C00H H00O 110.3 . . ?
C00M C00H H00O 110.3 . . ?
C00N C00H H00O 110.3 . . ?
C00O C00I C00J 107.6(7) . . ?
C00O C00I C00G 110.1(7) . . ?
C00J C00I C00G 110.0(8) . . ?
C00O C00I H00P 109.7 . . ?
C00J C00I H00P 109.7 . . ?
C00G C00I H00P 109.7 . . ?
C00H C00J C00I 110.3(6) . . ?
C00H C00J H00Q 109.6 . . ?
C00I C00J H00Q 109.6 . . ?
C00H C00J H00R 109.6 . . ?
C00I C00J H00R 109.6 . . ?
H00Q C00J H00R 108.1 . . ?
C00O C00K C00M 107.9(8) . . ?
C00O C00K C00L 109.9(9) . . ?
C00M C00K C00L 112.4(9) . . ?
C00O C00K H00S 108.9 . . ?
C00M C00K H00S 108.9 . . ?
C00L C00K H00S 108.9 . . ?
C00B C00L C00K 109.8(5) . . ?
C00B C00L H00T 109.7 . . ?
C00K C00L H00T 109.7 . . ?
C00B C00L H00U 109.7 . . ?
C00K C00L H00U 109.7 . . ?
H00T C00L H00U 108.2 . . ?
C00K C00M C00H 109.2(6) . . ?
C00K C00M H00V 109.8 . . ?
C00H C00M H00V 109.8 . . ?
C00K C00M H00W 109.8 . . ?
C00H C00M H00W 109.8 . . ?
H00V C00M H00W 108.3 . . ?
C00B C00N C00H 111.2(5) . . ?
C00B C00N H00X 109.4 . . ?
C00H C00N H00X 109.4 . . ?
C00B C00N H00Y 109.4 . . ?
C00H C00N H00Y 109.4 . . ?
H00X C00N H00Y 108.0 . . ?
C00K C00O C00I 110.5(8) . . ?
C00K C00O H00Z 109.6 . . ?
C00I C00O H00Z 109.6 . . ?
C00K C00O H 109.6 . . ?
C00I C00O H 109.6 . . ?
H00Z C00O H 108.1 . . ?

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
C00D O002 C005 C006 78.7(6) . . . . ?
C00D O002 C005 C008 -102.6(5) . . . . ?
C00F O004 C006 C007 -7.5(7) . . . . ?
C00F O004 C006 C005 170.3(4) . . . . ?
O002 C005 C006 O004 1.5(7) . . . . ?
C008 C005 C006 O004 -177.3(4) . . . . ?
O002 C005 C006 C007 179.4(4) . . . . ?
C008 C005 C006 C007 0.7(7) . . . . ?
O004 C006 C007 C009 178.3(4) . . . . ?
C005 C006 C007 C009 0.6(7) . . . . ?
C00E O003 C008 C00A 12.0(7) . . . . ?
C00E O003 C008 C005 -165.7(4) . . . . ?
O002 C005 C008 O003 -1.6(7) . . . . ?
C006 C005 C008 O003 177.2(4) . . . . ?
O002 C005 C008 C00A -179.4(4) . . . . ?
C006 C005 C008 C00A -0.6(7) . . . . ?
C006 C007 C009 C00A -1.8(7) . . . . ?
C006 C007 C009 C00C 178.1(4) . . . . ?
O003 C008 C00A C009 -178.2(4) . . . . ?
C005 C008 C00A C009 -0.6(7) . . . . ?
C007 C009 C00A C008 1.8(7) . . . . ?
C00C C009 C00A C008 -178.1(4) . . . . ?
C00C S001 C00B C00L -64.1(5) . . . . ?
C00C S001 C00B C00G 58.2(5) . . . . ?
C00C S001 C00B C00N 176.6(5) . . . . ?
C007 C009 C00C S001 -109.4(4) . . . . ?
C00A C009 C00C S001 70.5(5) . . . . ?
C00B S001 C00C C009 -172.6(4) . . . . ?
C00L C00B C00G C00I -58.9(8) . . . . ?
C00N C00B C00G C00I 59.2(9) . . . . ?
S001 C00B C00G C00I 176.7(6) . . . . ?
C00B C00G C00I C00O 57.8(11) . . . . ?
C00B C00G C00I C00J -60.6(10) . . . . ?
C00M C00H C00J C00I 60.4(9) . . . . ?
C00N C00H C00J C00I -57.5(10) . . . . ?
C00O C00I C00J C00H -61.1(10) . . . . ?
C00G C00I C00J C00H 58.9(9) . . . . ?
C00G C00B C00L C00K 60.3(9) . . . . ?
C00N C00B C00L C00K -57.1(9) . . . . ?
S001 C00B C00L C00K -174.8(7) . . . . ?
C00O C00K C00L C00B -61.1(12) . . . . ?
C00M C00K C00L C00B 59.0(11) . . . . ?
C00O C00K C00M C00H 62.4(11) . . . . ?
C00L C00K C00M C00H -58.9(10) . . . . ?
C00J C00H C00M C00K -60.9(9) . . . . ?
C00N C00H C00M C00K 57.9(10) . . . . ?
C00L C00B C00N C00H 59.2(10) . . . . ?
C00G C00B C00N C00H -58.3(10) . . . . ?
S001 C00B C00N C00H -179.8(7) . . . . ?
C00J C00H C00N C00B 57.8(11) . . . . ?
C00M C00H C00N C00B -59.0(11) . . . . ?
C00M C00K C00O C00I -63.5(11) . . . . ?
C00L C00K C00O C00I 59.3(11) . . . . ?
C00J C00I C00O C00K 62.1(10) . . . . ?
C00G C00I C00O C00K -57.7(11) . . . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.067

