# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_BN7550
_database_code_depnum_ccdc_archive 'CCDC 2311393'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2023-11-30 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_BN7550              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Thin plates poorly diffracted despite the use of copper radiation from
MM007HF rotating anode and decision was taken to fix an useful resolution upper
limit to d 0.93 \%A.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        4,6-diphenyl-3-(p-tolyl)-2H-pyran-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 O2'
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.459(4)
_cell_length_b                   18.500(7)
_cell_length_c                   11.372(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.575(12)
_cell_angle_gamma                90
_cell_volume                     1809.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1289
_cell_measurement_theta_min      7.0
_cell_measurement_theta_max      49.4

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.614
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_process_details   'Abscor (Higashi, Rigaku, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode mm007HF'
_diffrn_radiation_monochromator  'Confocal CMF Osmic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rapid 2 curved Imaging Plate'
_diffrn_measurement_device       
;
Crystal Goniometer chi partial
;
_diffrn_measurement_device_type  
;
Rigaku Spider 
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            14152
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         7.030
_diffrn_reflns_theta_max         55.984
_diffrn_reflns_theta_full        55.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2319
_reflns_number_gt                1401
_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_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)+(0.0962P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2317
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1895
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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
O1 O 0.1204(2) 0.02503(9) 0.28339(17) 0.0639(7) Uani 1 1 d . . . . .
C1 C 0.2270(3) -0.02055(13) 0.5045(3) 0.0524(8) Uani 1 1 d . . . . .
C6 C 0.2364(4) -0.08083(13) 0.5922(3) 0.0531(9) Uani 1 1 d . . . . .
C5 C 0.1261(4) -0.02980(17) 0.3687(3) 0.0606(9) Uani 1 1 d . . . . .
C4 C 0.2130(4) 0.08557(15) 0.3244(4) 0.0588(9) Uani 1 1 d . . . . .
C3 C 0.3054(4) 0.09431(14) 0.4489(3) 0.0602(9) Uani 1 1 d . . . . .
H3 H 0.366361 0.135724 0.475101 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3136(3) 0.04184(14) 0.5433(3) 0.0521(8) Uani 1 1 d . . . . .
O2 O 0.0444(2) -0.08174(11) 0.31744(19) 0.0799(8) Uani 1 1 d . . . . .
C9 C 0.2550(5) -0.19543(15) 0.7618(3) 0.0681(10) Uani 1 1 d . . . . .
C8 C 0.1136(4) -0.17216(15) 0.6675(3) 0.0711(10) Uani 1 1 d . . . . .
H8 H 0.023051 -0.195068 0.660837 0.085 Uiso 1 1 calc R U . . .
C7 C 0.1021(3) -0.11644(14) 0.5833(3) 0.0629(9) Uani 1 1 d . . . . .
H7 H 0.005425 -0.102672 0.520849 0.075 Uiso 1 1 calc R U . . .
C16 C 0.6192(5) 0.09050(17) 0.9342(4) 0.0924(12) Uani 1 1 d . . . . .
H16 H 0.686141 0.099901 1.019773 0.111 Uiso 1 1 calc R U . . .
C15 C 0.4643(5) 0.07499(17) 0.9011(4) 0.0857(12) Uani 1 1 d . . . . .
H15 H 0.426698 0.075854 0.964772 0.103 Uiso 1 1 calc R U . . .
C14 C 0.3648(4) 0.05831(14) 0.7761(4) 0.0685(10) Uani 1 1 d . . . . .
H14 H 0.261589 0.046873 0.756101 0.082 Uiso 1 1 calc R U . . .
C13 C 0.4186(4) 0.05860(13) 0.6804(3) 0.0556(9) Uani 1 1 d . . . . .
C12 C 0.2652(4) -0.25614(15) 0.8530(3) 0.1079(14) Uani 1 1 d . . . . .
H12A H 0.343847 -0.289771 0.855775 0.162 Uiso 1 1 calc R U . . .
H12B H 0.166787 -0.280428 0.823411 0.162 Uiso 1 1 calc R U . . .
H12C H 0.291538 -0.236953 0.937956 0.162 Uiso 1 1 calc R U . . .
C11 C 0.3794(4) -0.10513(15) 0.6857(3) 0.0615(9) Uani 1 1 d . . . . .
H11 H 0.470664 -0.083159 0.692012 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3873(4) -0.16057(15) 0.7681(3) 0.0698(10) Uani 1 1 d . . . . .
H10 H 0.483823 -0.175106 0.829616 0.084 Uiso 1 1 calc R U . . .
C18 C 0.5722(4) 0.07688(15) 0.7140(4) 0.0688(10) Uani 1 1 d . . . . .
H18 H 0.608783 0.079142 0.649838 0.083 Uiso 1 1 calc R U . . .
C17 C 0.6726(5) 0.09185(17) 0.8399(4) 0.0833(11) Uani 1 1 d . . . . .
H17 H 0.776159 0.102795 0.860374 0.100 Uiso 1 1 calc R U . . .
C20 C 0.2396(4) 0.20561(16) 0.2410(3) 0.0774(10) Uani 1 1 d . . . . .
H20 H 0.278377 0.223476 0.324997 0.093 Uiso 1 1 calc R U . . .
C19 C 0.1931(3) 0.13427(16) 0.2172(3) 0.0604(9) Uani 1 1 d . . . . .
C21 C 0.2287(4) 0.25044(17) 0.1407(4) 0.0893(12) Uani 1 1 d . . . . .
H21 H 0.261174 0.298273 0.157392 0.107 Uiso 1 1 calc R U . . .
C24 C 0.1341(4) 0.10901(18) 0.0916(4) 0.0812(11) Uani 1 1 d . . . . .
H24 H 0.101466 0.061244 0.074139 0.097 Uiso 1 1 calc R U . . .
C23 C 0.1234(4) 0.1545(2) -0.0086(3) 0.0930(12) Uani 1 1 d . . . . .
H23 H 0.084292 0.137185 -0.092950 0.112 Uiso 1 1 calc R U . . .
C22 C 0.1706(4) 0.2249(2) 0.0169(4) 0.0944(13) Uani 1 1 d . . . . .
H22 H 0.163012 0.255444 -0.050348 0.113 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
O1 C4 1.378(3) . ?
O1 C5 1.389(3) . ?
C1 C2 1.378(3) . ?
C1 C5 1.449(4) . ?
C1 C6 1.474(3) . ?
C6 C7 1.397(4) . ?
C6 C11 1.402(4) . ?
C5 O2 1.219(3) . ?
C4 C3 1.329(4) . ?
C4 C19 1.464(4) . ?
C3 C2 1.425(3) . ?
C3 H3 0.9300 . ?
C2 C13 1.492(4) . ?
C9 C10 1.382(4) . ?
C9 C8 1.390(4) . ?
C9 C12 1.504(4) . ?
C8 C7 1.380(4) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C16 C17 1.362(5) . ?
C16 C15 1.383(5) . ?
C16 H16 0.9300 . ?
C15 C14 1.375(4) . ?
C15 H15 0.9300 . ?
C14 C13 1.381(4) . ?
C14 H14 0.9300 . ?
C13 C18 1.381(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 C10 1.370(4) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C18 C17 1.377(4) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C20 C21 1.379(4) . ?
C20 C19 1.382(4) . ?
C20 H20 0.9300 . ?
C19 C24 1.381(4) . ?
C21 C22 1.364(4) . ?
C21 H21 0.9300 . ?
C24 C23 1.385(4) . ?
C24 H24 0.9300 . ?
C23 C22 1.368(4) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?

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
C4 O1 C5 121.5(3) . . ?
C2 C1 C5 118.7(3) . . ?
C2 C1 C6 123.8(3) . . ?
C5 C1 C6 117.4(3) . . ?
C7 C6 C11 117.7(3) . . ?
C7 C6 C1 120.7(3) . . ?
C11 C6 C1 121.6(3) . . ?
O2 C5 O1 114.1(3) . . ?
O2 C5 C1 127.5(3) . . ?
O1 C5 C1 118.4(3) . . ?
C3 C4 O1 120.2(3) . . ?
C3 C4 C19 127.8(3) . . ?
O1 C4 C19 112.0(3) . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 C13 123.9(3) . . ?
C3 C2 C13 116.7(3) . . ?
C10 C9 C8 117.1(3) . . ?
C10 C9 C12 121.0(3) . . ?
C8 C9 C12 121.9(3) . . ?
C7 C8 C9 122.6(3) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C13 C18 118.2(3) . . ?
C14 C13 C2 121.3(3) . . ?
C18 C13 C2 120.5(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 C6 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C17 C18 C13 121.9(3) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
C16 C17 C18 119.6(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C24 C19 C20 119.0(3) . . ?
C24 C19 C4 120.7(3) . . ?
C20 C19 C4 120.3(3) . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C24 C23 120.3(3) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C21 C22 C23 120.3(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?

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
C2 C1 C6 C7 138.7(3) . . . . ?
C5 C1 C6 C7 -44.6(3) . . . . ?
C2 C1 C6 C11 -42.3(4) . . . . ?
C5 C1 C6 C11 134.5(3) . . . . ?
C4 O1 C5 O2 -175.9(2) . . . . ?
C4 O1 C5 C1 2.9(3) . . . . ?
C2 C1 C5 O2 178.3(3) . . . . ?
C6 C1 C5 O2 1.4(4) . . . . ?
C2 C1 C5 O1 -0.4(4) . . . . ?
C6 C1 C5 O1 -177.3(2) . . . . ?
C5 O1 C4 C3 -3.1(4) . . . . ?
C5 O1 C4 C19 177.2(2) . . . . ?
O1 C4 C3 C2 0.7(4) . . . . ?
C19 C4 C3 C2 -179.7(3) . . . . ?
C5 C1 C2 C3 -1.9(4) . . . . ?
C6 C1 C2 C3 174.8(2) . . . . ?
C5 C1 C2 C13 178.4(2) . . . . ?
C6 C1 C2 C13 -4.9(4) . . . . ?
C4 C3 C2 C1 1.8(4) . . . . ?
C4 C3 C2 C13 -178.5(3) . . . . ?
C10 C9 C8 C7 -0.6(5) . . . . ?
C12 C9 C8 C7 179.8(3) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C11 C6 C7 C8 1.7(4) . . . . ?
C1 C6 C7 C8 -179.2(2) . . . . ?
C17 C16 C15 C14 2.4(5) . . . . ?
C16 C15 C14 C13 -1.6(5) . . . . ?
C15 C14 C13 C18 -0.9(4) . . . . ?
C15 C14 C13 C2 -179.1(2) . . . . ?
C1 C2 C13 C14 -55.1(4) . . . . ?
C3 C2 C13 C14 125.3(3) . . . . ?
C1 C2 C13 C18 126.7(3) . . . . ?
C3 C2 C13 C18 -52.9(3) . . . . ?
C7 C6 C11 C10 -1.8(4) . . . . ?
C1 C6 C11 C10 179.2(2) . . . . ?
C6 C11 C10 C9 0.6(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C12 C9 C10 C11 -179.8(3) . . . . ?
C14 C13 C18 C17 2.5(4) . . . . ?
C2 C13 C18 C17 -179.2(3) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C13 C18 C17 C16 -1.7(5) . . . . ?
C21 C20 C19 C24 -0.7(4) . . . . ?
C21 C20 C19 C4 176.4(3) . . . . ?
C3 C4 C19 C24 158.9(3) . . . . ?
O1 C4 C19 C24 -21.4(4) . . . . ?
C3 C4 C19 C20 -18.1(4) . . . . ?
O1 C4 C19 C20 161.5(2) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C19 C24 C23 0.6(5) . . . . ?
C4 C19 C24 C23 -176.5(3) . . . . ?
C19 C24 C23 C22 -0.4(5) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C24 C23 C22 C21 0.3(5) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
