# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_la_ap_320a_a
_database_code_depnum_ccdc_archive 'CCDC 1548930'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Phenyl 4-hydroxy-3-(3-oxocyclohex-1-en-1-yl)-4-phenyltetrahydrothiophene-2-carboxylate'

_chemical_formula_moiety         'C23 H22 O4 S'
_chemical_formula_sum            'C23 H22 O4 S'
_chemical_formula_weight         394.46

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   5.6715(2)
_cell_length_b                   8.7531(2)
_cell_length_c                   10.1807(2)
_cell_angle_alpha                84.0710(10)
_cell_angle_beta                 82.0360(10)
_cell_angle_gamma                83.6930(10)
_cell_volume                     495.50(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    382
_cell_measurement_theta_min      8.7879
_cell_measurement_theta_max      74.4559
_cell_measurement_temperature    100(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.053
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             208

_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.5878
_exptl_absorpt_correction_T_max  0.7536
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray microsource'
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       ?
_d_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            5975
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.403
_diffrn_reflns_theta_max         84.600
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.732
_diffrn_reflns_point_group_measured_fraction_full 0.851
_reflns_number_total             3276
_reflns_number_gt                3241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_max     0.605
_reflns_Friedel_fraction_full    0.721

_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       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_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)+(0.0241P)²+0.2735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3276
_refine_ls_number_parameters     265
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.009
_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
S1 S 0.62477(15) 0.81605(11) 0.29460(9) 0.0510(3) Uani 1 1 d . . . . .
O1 O 0.9094(4) 0.7039(3) 0.5410(3) 0.0449(6) Uani 1 1 d . . . . .
H1 H 0.959(3) 0.693(6) 0.464(5) 0.067 Uiso 1 1 calc R U . . .
C1 C 0.5892(7) 0.8795(5) 0.4608(3) 0.0453(9) Uani 1 1 d . . . . .
H1A H 0.6945 0.9616 0.4643 0.054 Uiso 1 1 calc R U . . .
H1B H 0.4214 0.9206 0.4871 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6583(6) 0.7370(4) 0.5543(3) 0.0344(7) Uani 1 1 d . . . . .
O2 O 0.4725(4) 0.4376(3) 0.2205(3) 0.0523(7) Uani 1 1 d . . . . .
C3 C 0.5354(6) 0.6053(4) 0.5060(3) 0.0328(7) Uani 1 1 d . . . . .
H3 H 0.3588 0.6310 0.5266 0.039 Uiso 1 1 calc R U . . .
O3 O 0.1880(5) 0.6012(4) 0.3140(3) 0.0661(10) Uani 1 1 d . . . . .
C4 C 0.5942(6) 0.6138(4) 0.3528(3) 0.0378(8) Uani 1 1 d . . . . .
H4 H 0.7479 0.5498 0.3275 0.045 Uiso 1 1 calc R U . . .
O4 O 1.0291(7) 0.1221(5) 0.5657(5) 0.0951(13) Uani 1 1 d . . . . .
C5 C 0.3928(6) 0.5542(5) 0.2951(3) 0.0396(8) Uani 1 1 d . . . . .
C6 C 0.2978(7) 0.3582(5) 0.1768(4) 0.0480(10) Uani 1 1 d . . . . .
C8 C 0.0954(11) 0.1332(7) 0.1925(6) 0.0786(15) Uani 1 1 d . . . . .
H8 H 0.0698 0.0323 0.2321 0.094 Uiso 1 1 calc R U . . .
C7 C 0.2635(10) 0.2145(6) 0.2365(6) 0.0690(13) Uani 1 1 d . . . . .
H7 H 0.3518 0.1705 0.3062 0.083 Uiso 1 1 calc R U . . .
C9 C -0.0310(9) 0.1966(7) 0.0944(6) 0.0765(16) Uani 1 1 d . . . . .
H9 H -0.1464 0.1407 0.0662 0.092 Uiso 1 1 calc R U . . .
C10 C 0.0057(10) 0.3407(7) 0.0354(6) 0.0800(16) Uani 1 1 d . . . . .
H10 H -0.0839 0.3843 -0.0339 0.096 Uiso 1 1 calc R U . . .
C11 C 0.1728(10) 0.4237(6) 0.0757(5) 0.0646(12) Uani 1 1 d . . . . .
H11 H 0.2003 0.5237 0.0344 0.077 Uiso 1 1 calc R U . . .
C12 C 0.5728(6) 0.7623(4) 0.6995(3) 0.0333(7) Uani 1 1 d . . . . .
C13 C 0.3424(6) 0.8262(4) 0.7389(4) 0.0411(8) Uani 1 1 d . . . . .
H13 H 0.2345 0.8521 0.6747 0.049 Uiso 1 1 calc R U . . .
C14 C 0.2677(7) 0.8527(5) 0.8706(4) 0.0484(9) Uani 1 1 d . . . . .
H14 H 0.1106 0.8990 0.8957 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4197(8) 0.8125(5) 0.9655(4) 0.0531(10) Uani 1 1 d . . . . .
H15 H 0.3691 0.8318 1.0557 0.064 Uiso 1 1 calc R U . . .
C16 C 0.6465(8) 0.7437(5) 0.9280(4) 0.0533(10) Uani 1 1 d . . . . .
H16 H 0.7507 0.7129 0.9934 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7235(6) 0.7193(5) 0.7965(4) 0.0429(8) Uani 1 1 d . . . . .
H17 H 0.8807 0.6726 0.7720 0.052 Uiso 1 1 calc R U . . .
C18 C 0.5950(6) 0.4484(4) 0.5762(3) 0.0389(8) Uani 1 1 d . . . . .
C19 C 0.7888(7) 0.3552(5) 0.5370(4) 0.0525(10) Uani 1 1 d . . . . .
H19 H 0.8893 0.3875 0.4587 0.063 Uiso 1 1 calc R U . . .
C20 C 0.8553(8) 0.2051(5) 0.6085(5) 0.0606(11) Uani 1 1 d . . . . .
C21 C 0.7040(12) 0.1642(6) 0.7339(6) 0.0841(17) Uani 1 1 d . . . . .
H21A H 0.7691 0.2034 0.8079 0.101 Uiso 0.65(2) 1 calc R U P A 1
H21B H 0.7124 0.0504 0.7500 0.101 Uiso 0.65(2) 1 calc R U P A 1
H21C H 0.6166 0.0766 0.7200 0.101 Uiso 0.35(2) 1 calc R U P A 2
H21D H 0.8110 0.1267 0.8019 0.101 Uiso 0.35(2) 1 calc R U P A 2
C23 C 0.4226(9) 0.4025(6) 0.6954(5) 0.0640(12) Uani 1 1 d . . . . .
H23A H 0.2572 0.4342 0.6757 0.077 Uiso 0.65(2) 1 calc R U P A 1
H23B H 0.4493 0.4577 0.7713 0.077 Uiso 0.65(2) 1 calc R U P A 1
H23C H 0.2824 0.3646 0.6656 0.077 Uiso 0.35(2) 1 calc R U P A 2
H23D H 0.3653 0.4940 0.7447 0.077 Uiso 0.35(2) 1 calc R U P A 2
C22A C 0.450(2) 0.2265(10) 0.7353(13) 0.070(4) Uani 0.65(2) 1 d . . P A 1
H22A H 0.3635 0.2052 0.8257 0.084 Uiso 0.65(2) 1 calc R U P A 1
H22B H 0.3752 0.1732 0.6729 0.084 Uiso 0.65(2) 1 calc R U P A 1
C22B C 0.537(5) 0.278(3) 0.7869(18) 0.084(8) Uani 0.35(2) 1 d . . P A 2
H22C H 0.6152 0.3304 0.8485 0.101 Uiso 0.35(2) 1 calc R U P A 2
H22D H 0.4059 0.2256 0.8416 0.101 Uiso 0.35(2) 1 calc R U P A 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 C1 1.813(4) . ?
S1 C4 1.827(4) . ?
O1 C2 1.412(4) . ?
O1 H1 0.80(5) . ?
C1 C2 1.539(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C12 1.522(4) . ?
C2 C3 1.563(5) . ?
O2 C5 1.336(4) . ?
O2 C6 1.415(5) . ?
C3 C18 1.508(5) . ?
C3 C4 1.545(4) . ?
C3 H3 1.0000 . ?
O3 C5 1.185(4) . ?
C4 C5 1.517(5) . ?
C4 H4 1.0000 . ?
O4 C20 1.216(6) . ?
C6 C7 1.361(7) . ?
C6 C11 1.372(6) . ?
C8 C9 1.347(9) . ?
C8 C7 1.396(7) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.364(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.386(5) . ?
C12 C17 1.390(5) . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.335(6) . ?
C18 C23 1.499(5) . ?
C19 C20 1.472(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.471(8) . ?
C21 C22B 1.40(2) . ?
C21 C22A 1.484(13) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C23 C22B 1.51(2) . ?
C23 C22A 1.548(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 H23C 0.9900 . ?
C23 H23D 0.9900 . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C22B H22C 0.9900 . ?
C22B H22D 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
C1 S1 C4 94.34(17) . . ?
C2 O1 H1 109.5 . . ?
C2 C1 S1 106.5(3) . . ?
C2 C1 H1A 110.4 . . ?
S1 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
S1 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
O1 C2 C12 107.6(3) . . ?
O1 C2 C1 110.3(3) . . ?
C12 C2 C1 111.7(3) . . ?
O1 C2 C3 111.3(3) . . ?
C12 C2 C3 112.2(3) . . ?
C1 C2 C3 103.8(3) . . ?
C5 O2 C6 116.8(3) . . ?
C18 C3 C4 114.5(3) . . ?
C18 C3 C2 113.8(3) . . ?
C4 C3 C2 107.1(3) . . ?
C18 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C5 C4 C3 109.1(3) . . ?
C5 C4 S1 111.2(3) . . ?
C3 C4 S1 107.0(2) . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
S1 C4 H4 109.8 . . ?
O3 C5 O2 122.8(3) . . ?
O3 C5 C4 125.5(3) . . ?
O2 C5 C4 111.7(3) . . ?
C7 C6 C11 121.9(4) . . ?
C7 C6 O2 117.6(4) . . ?
C11 C6 O2 120.5(4) . . ?
C9 C8 C7 120.6(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C6 C7 C8 118.3(5) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C8 C9 C10 120.4(5) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 120.4(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 118.4(5) . . ?
C6 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C13 C12 C17 118.4(3) . . ?
C13 C12 C2 121.1(3) . . ?
C17 C12 C2 120.6(3) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.2(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.5(4) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 121.3(4) . . ?
C19 C18 C3 123.0(3) . . ?
C23 C18 C3 115.7(3) . . ?
C18 C19 C20 123.5(4) . . ?
C18 C19 H19 118.2 . . ?
C20 C19 H19 118.2 . . ?
O4 C20 C21 122.6(5) . . ?
O4 C20 C19 120.9(5) . . ?
C21 C20 C19 116.5(4) . . ?
C22B C21 C20 118.1(9) . . ?
C20 C21 C22A 113.8(6) . . ?
C20 C21 H21A 108.8 . . ?
C22A C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22A C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C22B C21 H21C 107.8 . . ?
C20 C21 H21C 107.8 . . ?
C22B C21 H21D 107.8 . . ?
C20 C21 H21D 107.8 . . ?
H21C C21 H21D 107.1 . . ?
C18 C23 C22B 111.6(8) . . ?
C18 C23 C22A 112.3(5) . . ?
C18 C23 H23A 109.1 . . ?
C22A C23 H23A 109.1 . . ?
C18 C23 H23B 109.1 . . ?
C22A C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C18 C23 H23C 109.3 . . ?
C22B C23 H23C 109.3 . . ?
C18 C23 H23D 109.3 . . ?
C22B C23 H23D 109.3 . . ?
H23C C23 H23D 108.0 . . ?
C21 C22A C23 112.0(7) . . ?
C21 C22A H22A 109.2 . . ?
C23 C22A H22A 109.2 . . ?
C21 C22A H22B 109.2 . . ?
C23 C22A H22B 109.2 . . ?
H22A C22A H22B 107.9 . . ?
C21 C22B C23 119.9(13) . . ?
C21 C22B H22C 107.3 . . ?
C23 C22B H22C 107.3 . . ?
C21 C22B H22D 107.3 . . ?
C23 C22B H22D 107.3 . . ?
H22C C22B H22D 106.9 . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044

