# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_md_jl3
_database_code_depnum_ccdc_archive 'CCDC 2473119'
loop_
_audit_author_name
_audit_author_address
'Lin Jiang'
;Yunnan Minzu University
China
;
_audit_update_record             
;
2025-07-16 deposited with the CCDC.	2025-10-09 downloaded from the CCDC.
;
_chemical_name_systematic        
(1R,2S,3S)-1-phenyl-2-(thiophene-2-carbonyl)spiro[2.5]oct-7-en-4-one
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H16 O2 S'
_chemical_formula_sum            'C19 H16 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         308.38

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   10.3039(2)
_cell_length_b                   7.84730(10)
_cell_length_c                   37.4016(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3024.21(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.3626
_cell_measurement_theta_max      68.1199
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296

_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_T_max  0.73

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            17332
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       42

_refine_special_details          
;
;

_reflns_number_total             2769
_reflns_number_gt                2531
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1529
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         2769
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0934P)²+1.8484P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.600
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.59498(6) 0.30634(9) 0.51423(2) 0.0417(2) Uani d . . . 1 . .
O O1 0.39256(14) 0.4328(2) 0.56460(4) 0.0338(4) Uani d . . . 1 . .
O O2 0.67635(14) 0.72775(19) 0.65875(4) 0.0334(4) Uani d . . . 1 . .
C C1 0.3884(3) 0.3847(3) 0.74700(6) 0.0376(5) Uani d . . . 1 . .
H H1 0.377902 0.343749 0.770722 0.045 Uiso calc U . R 1 . .
C C2 0.4962(2) 0.3380(3) 0.72726(6) 0.0359(5) Uani d . . . 1 . .
H H11 0.560801 0.267516 0.737736 0.043 Uiso calc U . R 1 . .
C C3 0.5108(2) 0.3937(2) 0.69219(6) 0.0292(4) Uani d . . . 1 . .
H H14 0.585715 0.36223 0.678937 0.035 Uiso calc U . R 1 . .
C C4 0.41605(19) 0.4951(2) 0.67645(5) 0.0236(4) Uani d . . . 1 . .
C C5 0.41644(18) 0.5430(2) 0.63784(5) 0.0228(4) Uani d . . . 1 . .
H H10 0.33083 0.52197 0.626047 0.027 Uiso calc U . R 1 . .
C C6 0.52794(19) 0.5171(2) 0.61305(5) 0.0227(4) Uani d . . . 1 . .
H H15 0.610033 0.477047 0.624577 0.027 Uiso calc U . R 1 . .
C C7 0.50255(19) 0.4473(2) 0.57644(5) 0.0243(4) Uani d . . . 1 . .
C C8 0.6157(2) 0.3960(2) 0.55555(5) 0.0251(4) Uani d . . . 1 . .
C C9 0.75094(19) 0.4127(3) 0.56510(5) 0.0265(4) Uani d . . . 1 . .
H H16 0.784237 0.457088 0.586875 0.032 Uiso calc U . R 1 . .
C C10 0.8265(2) 0.3489(3) 0.53516(6) 0.0392(5) Uani d . . . 1 . .
H H2 0.918716 0.34964 0.535039 0.047 Uiso calc U . R 1 . .
C C11 0.7561(2) 0.2888(3) 0.50761(6) 0.0382(5) Uani d . . . 1 . .
H H3 0.793416 0.241421 0.486614 0.046 Uiso calc U . R 1 . .
C C12 0.48699(19) 0.7001(2) 0.62248(5) 0.0223(4) Uani d . . . 1 . .
C C13 0.57805(19) 0.7921(2) 0.64716(5) 0.0242(4) Uani d . . . 1 . .
C C14 0.5349(2) 0.9685(2) 0.65747(6) 0.0291(5) Uani d . . . 1 . .
H H4 0.607245 1.027146 0.669793 0.035 Uiso calc U . R 1 . .
H H5 0.461871 0.959464 0.674571 0.035 Uiso calc U . R 1 . .
C C15 0.4917(2) 1.0768(3) 0.62535(6) 0.0314(5) Uani d . . . 1 . .
H H9 0.437901 1.17275 0.634058 0.038 Uiso calc U . R 1 . .
H H8 0.56947 1.12555 0.61363 0.038 Uiso calc U . R 1 . .
C C16 0.4159(2) 0.9775(3) 0.59839(6) 0.0298(5) Uani d . . . 1 . .
H H6 0.367245 1.038898 0.581071 0.036 Uiso calc U . R 1 . .
C C17 0.41268(19) 0.8084(3) 0.59726(6) 0.0265(4) Uani d . . . 1 . .
H H7 0.360657 0.754698 0.579575 0.032 Uiso calc U . R 1 . .
C C18 0.2956(2) 0.4913(3) 0.73215(6) 0.0343(5) Uani d . . . 1 . .
H H12 0.223035 0.526953 0.745904 0.041 Uiso calc U . R 1 . .
C C19 0.3096(2) 0.5456(3) 0.69701(6) 0.0279(4) Uani d . . . 1 . .
H H13 0.245835 0.618283 0.686806 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . 1.684(3) ?
S1 C8 . 1.712(2) ?
O1 C7 . 1.222(3) ?
O2 C13 . 1.212(3) ?
C1 C2 . 1.384(4) ?
C1 C18 . 1.386(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.390(3) ?
C2 H11 . 0.95 ?
C3 C4 . 1.390(3) ?
C3 H14 . 0.95 ?
C4 C19 . 1.397(3) ?
C4 C5 . 1.492(3) ?
C5 C6 . 1.490(3) ?
C5 C12 . 1.542(3) ?
C5 H10 . 1.0 ?
C6 C7 . 1.498(3) ?
C6 C12 . 1.538(2) ?
C6 H15 . 1.0 ?
C7 C8 . 1.460(3) ?
C8 C9 . 1.444(3) ?
C9 C10 . 1.453(3) ?
C9 H16 . 0.95 ?
C10 C11 . 1.346(3) ?
C10 H2 . 0.95 ?
C11 H3 . 0.95 ?
C12 C17 . 1.483(3) ?
C12 C13 . 1.501(3) ?
C13 C14 . 1.504(3) ?
C14 C15 . 1.538(3) ?
C14 H4 . 0.99 ?
C14 H5 . 0.99 ?
C15 C16 . 1.495(3) ?
C15 H9 . 0.99 ?
C15 H8 . 0.99 ?
C16 C17 . 1.328(3) ?
C16 H6 . 0.95 ?
C17 H7 . 0.95 ?
C18 C19 . 1.389(3) ?
C18 H12 . 0.95 ?
C19 H13 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C8 . . 92.47(11) ?
C2 C1 C18 . . 120.0(2) ?
C2 C1 H1 . . 120.0 ?
C18 C1 H1 . . 120.0 ?
C1 C2 C3 . . 120.5(2) ?
C1 C2 H11 . . 119.8 ?
C3 C2 H11 . . 119.8 ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H14 . . 119.9 ?
C2 C3 H14 . . 119.9 ?
C3 C4 C19 . . 118.74(19) ?
C3 C4 C5 . . 123.51(18) ?
C19 C4 C5 . . 117.59(18) ?
C6 C5 C4 . . 124.74(17) ?
C6 C5 C12 . . 60.91(12) ?
C4 C5 C12 . . 124.27(16) ?
C6 C5 H10 . . 112.5 ?
C4 C5 H10 . . 112.5 ?
C12 C5 H10 . . 112.5 ?
C5 C6 C7 . . 118.94(16) ?
C5 C6 C12 . . 61.22(12) ?
C7 C6 C12 . . 120.22(16) ?
C5 C6 H15 . . 115.3 ?
C7 C6 H15 . . 115.3 ?
C12 C6 H15 . . 115.3 ?
O1 C7 C8 . . 121.41(18) ?
O1 C7 C6 . . 121.83(18) ?
C8 C7 C6 . . 116.77(17) ?
C9 C8 C7 . . 127.83(17) ?
C9 C8 S1 . . 112.39(15) ?
C7 C8 S1 . . 119.78(15) ?
C8 C9 C10 . . 107.18(18) ?
C8 C9 H16 . . 126.4 ?
C10 C9 H16 . . 126.4 ?
C11 C10 C9 . . 115.0(2) ?
C11 C10 H2 . . 122.5 ?
C9 C10 H2 . . 122.5 ?
C10 C11 S1 . . 112.97(17) ?
C10 C11 H3 . . 123.5 ?
S1 C11 H3 . . 123.5 ?
C17 C12 C13 . . 115.98(17) ?
C17 C12 C6 . . 122.08(17) ?
C13 C12 C6 . . 114.75(16) ?
C17 C12 C5 . . 116.87(16) ?
C13 C12 C5 . . 116.75(16) ?
C6 C12 C5 . . 57.87(12) ?
O2 C13 C12 . . 122.80(18) ?
O2 C13 C14 . . 122.61(19) ?
C12 C13 C14 . . 114.55(17) ?
C13 C14 C15 . . 113.21(16) ?
C13 C14 H4 . . 108.9 ?
C15 C14 H4 . . 108.9 ?
C13 C14 H5 . . 108.9 ?
C15 C14 H5 . . 108.9 ?
H4 C14 H5 . . 107.7 ?
C16 C15 C14 . . 112.96(17) ?
C16 C15 H9 . . 109.0 ?
C14 C15 H9 . . 109.0 ?
C16 C15 H8 . . 109.0 ?
C14 C15 H8 . . 109.0 ?
H9 C15 H8 . . 107.8 ?
C17 C16 C15 . . 123.7(2) ?
C17 C16 H6 . . 118.1 ?
C15 C16 H6 . . 118.1 ?
C16 C17 C12 . . 122.7(2) ?
C16 C17 H7 . . 118.7 ?
C12 C17 H7 . . 118.7 ?
C1 C18 C19 . . 119.5(2) ?
C1 C18 H12 . . 120.2 ?
C19 C18 H12 . . 120.2 ?
C18 C19 C4 . . 121.0(2) ?
C18 C19 H13 . . 119.5 ?
C4 C19 H13 . . 119.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 C1 C2 C3 . . . . -1.7(3) ?
C1 C2 C3 C4 . . . . -0.8(3) ?
C2 C3 C4 C19 . . . . 2.8(3) ?
C2 C3 C4 C5 . . . . -172.54(18) ?
C3 C4 C5 C6 . . . . -11.9(3) ?
C19 C4 C5 C6 . . . . 172.74(17) ?
C3 C4 C5 C12 . . . . -87.8(2) ?
C19 C4 C5 C12 . . . . 96.8(2) ?
C4 C5 C6 C7 . . . . 135.89(18) ?
C12 C5 C6 C7 . . . . -110.64(19) ?
C4 C5 C6 C12 . . . . -113.5(2) ?
C5 C6 C7 O1 . . . . 10.1(3) ?
C12 C6 C7 O1 . . . . -61.5(3) ?
C5 C6 C7 C8 . . . . -169.48(17) ?
C12 C6 C7 C8 . . . . 118.86(19) ?
O1 C7 C8 C9 . . . . 176.8(2) ?
C6 C7 C8 C9 . . . . -3.6(3) ?
O1 C7 C8 S1 . . . . -2.4(3) ?
C6 C7 C8 S1 . . . . 177.16(13) ?
C11 S1 C8 C9 . . . . -0.47(17) ?
C11 S1 C8 C7 . . . . 178.87(17) ?
C7 C8 C9 C10 . . . . -178.1(2) ?
S1 C8 C9 C10 . . . . 1.2(2) ?
C8 C9 C10 C11 . . . . -1.6(3) ?
C9 C10 C11 S1 . . . . 1.3(3) ?
C8 S1 C11 C10 . . . . -0.5(2) ?
C5 C6 C12 C17 . . . . -103.7(2) ?
C7 C6 C12 C17 . . . . 4.9(3) ?
C5 C6 C12 C13 . . . . 107.20(18) ?
C7 C6 C12 C13 . . . . -144.19(18) ?
C7 C6 C12 C5 . . . . 108.60(19) ?
C6 C5 C12 C17 . . . . 112.64(19) ?
C4 C5 C12 C17 . . . . -133.15(19) ?
C6 C5 C12 C13 . . . . -103.72(18) ?
C4 C5 C12 C13 . . . . 10.5(3) ?
C4 C5 C12 C6 . . . . 114.2(2) ?
C17 C12 C13 O2 . . . . -151.0(2) ?
C6 C12 C13 O2 . . . . 0.1(3) ?
C5 C12 C13 O2 . . . . 65.1(3) ?
C17 C12 C13 C14 . . . . 31.2(2) ?
C6 C12 C13 C14 . . . . -177.68(16) ?
C5 C12 C13 C14 . . . . -112.72(19) ?
O2 C13 C14 C15 . . . . 134.2(2) ?
C12 C13 C14 C15 . . . . -48.0(2) ?
C13 C14 C15 C16 . . . . 39.6(3) ?
C14 C15 C16 C17 . . . . -15.7(3) ?
C15 C16 C17 C12 . . . . -1.3(3) ?
C13 C12 C17 C16 . . . . -6.3(3) ?
C6 C12 C17 C16 . . . . -155.1(2) ?
C5 C12 C17 C16 . . . . 137.6(2) ?
C2 C1 C18 C19 . . . . 2.3(3) ?
C1 C18 C19 C4 . . . . -0.3(3) ?
C3 C4 C19 C18 . . . . -2.2(3) ?
C5 C4 C19 C18 . . . . 173.36(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C10 H2 S1 2_556 0.95 2.86 3.542(2) 129.4 ?
C11 H3 O1 2_556 0.95 2.57 3.506(3) 170.7 ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
