# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_240526a
_database_code_depnum_ccdc_archive 'CCDC 2381765'
loop_
_audit_author_name
_audit_author_address
'Liao Minghong '
;Guizhou University
China
;
_audit_update_record             
;
2024-09-04 deposited with the CCDC.	2025-01-14 downloaded from the CCDC.
;
_audit_creation_date             2024-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 O2'
_chemical_formula_sum            'C15 H10 O2'
_chemical_formula_weight         222.23
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4203(11)
_cell_length_b                   8.0074(11)
_cell_length_c                   10.4911(13)
_cell_angle_alpha                72.384(6)
_cell_angle_beta                 88.735(8)
_cell_angle_gamma                65.864(5)
_cell_volume                     538.47(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    963
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1800
_cell_measurement_theta_min      4.0980
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3610
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         3.454
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.3148
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1151
_reflns_number_total             1901
_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       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+0.0183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1435
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.2625(3) 0.0614(2) 0.45907(18) 0.0772(6) Uani 1 1 d . . . . .
O2 O 0.3474(3) -0.0438(2) 0.72835(17) 0.0786(6) Uani 1 1 d . . . . .
C1 C 0.2726(3) 0.1783(3) 0.5068(2) 0.0510(6) Uani 1 1 d . . . . .
C2 C 0.3139(3) 0.1210(3) 0.6602(2) 0.0514(6) Uani 1 1 d . . . . .
C3 C 0.3109(3) 0.2678(3) 0.7183(2) 0.0445(6) Uani 1 1 d . . . . .
C4 C 0.2792(3) 0.4542(3) 0.6356(2) 0.0396(6) Uani 1 1 d . . . . .
C5 C 0.2447(3) 0.5081(3) 0.4866(2) 0.0387(5) Uani 1 1 d . . . . .
C6 C 0.2434(3) 0.3749(3) 0.4252(2) 0.0435(6) Uani 1 1 d . . . . .
C7 C 0.2102(4) 0.4288(4) 0.2856(2) 0.0551(7) Uani 1 1 d . . . . .
H7 H 0.210583 0.339619 0.245683 0.066 Uiso 1 1 calc R U . . .
C8 C 0.1769(4) 0.6120(4) 0.2065(2) 0.0560(7) Uani 1 1 d . . . . .
H8 H 0.155657 0.645758 0.113312 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1745(3) 0.7480(3) 0.2643(2) 0.0494(6) Uani 1 1 d . . . . .
C10 C 0.2079(3) 0.6941(3) 0.4033(2) 0.0437(6) Uani 1 1 d . . . . .
H10 H 0.205696 0.784854 0.442221 0.052 Uiso 1 1 calc R U . . .
C11 C 0.3389(4) 0.2191(3) 0.8576(2) 0.0554(7) Uani 1 1 d . . . . .
H11 H 0.356885 0.096136 0.911352 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3404(4) 0.3494(4) 0.9170(2) 0.0631(8) Uani 1 1 d . . . . .
H12 H 0.359775 0.314877 1.010319 0.076 Uiso 1 1 calc R U . . .
C13 C 0.3128(4) 0.5321(4) 0.8374(2) 0.0586(7) Uani 1 1 d . . . . .
H13 H 0.315179 0.620625 0.877064 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2816(3) 0.5839(3) 0.6983(2) 0.0490(6) Uani 1 1 d . . . . .
H14 H 0.261797 0.707941 0.645783 0.059 Uiso 1 1 calc R U . . .
C15 C 0.1301(4) 0.9523(4) 0.1792(2) 0.0708(8) Uani 1 1 d . . . . .
H15A H -0.010991 1.029206 0.165480 0.106 Uiso 1 1 calc R U . . .
H15B H 0.179069 0.952558 0.093705 0.106 Uiso 1 1 calc R U . . .
H15C H 0.193842 1.005264 0.224170 0.106 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 C1 1.214(3) . ?
O2 C2 1.218(2) . ?
C1 C2 1.535(3) . ?
C1 C6 1.474(3) . ?
C2 C3 1.472(3) . ?
C3 C4 1.405(3) . ?
C3 C11 1.390(3) . ?
C4 C5 1.488(3) . ?
C4 C14 1.393(3) . ?
C5 C6 1.407(3) . ?
C5 C10 1.395(3) . ?
C6 C7 1.392(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(3) . ?
C9 C10 1.386(3) . ?
C9 C15 1.506(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.372(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O1 C1 C2 118.7(2) . . ?
O1 C1 C6 123.5(2) . . ?
C6 C1 C2 117.8(2) . . ?
O2 C2 C1 118.5(2) . . ?
O2 C2 C3 123.0(2) . . ?
C3 C2 C1 118.55(18) . . ?
C4 C3 C2 121.1(2) . . ?
C11 C3 C2 118.66(19) . . ?
C11 C3 C4 120.3(2) . . ?
C3 C4 C5 120.4(2) . . ?
C14 C4 C3 117.57(19) . . ?
C14 C4 C5 122.06(17) . . ?
C6 C5 C4 121.20(17) . . ?
C10 C5 C4 121.0(2) . . ?
C10 C5 C6 117.74(19) . . ?
C5 C6 C1 120.92(19) . . ?
C7 C6 C1 118.9(2) . . ?
C7 C6 C5 120.16(19) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C15 121.3(2) . . ?
C10 C9 C8 118.73(19) . . ?
C10 C9 C15 120.0(2) . . ?
C5 C10 H10 118.9 . . ?
C9 C10 C5 122.1(2) . . ?
C9 C10 H10 118.9 . . ?
C3 C11 H11 119.5 . . ?
C12 C11 C3 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C4 C14 H14 119.3 . . ?
C13 C14 C4 121.46(19) . . ?
C13 C14 H14 119.3 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C1 C2 O2 4.5(4) . . . . ?
O1 C1 C2 C3 -175.4(2) . . . . ?
O1 C1 C6 C5 176.0(2) . . . . ?
O1 C1 C6 C7 -2.6(4) . . . . ?
O2 C2 C3 C4 177.5(2) . . . . ?
O2 C2 C3 C11 -2.9(4) . . . . ?
C1 C2 C3 C4 -2.6(3) . . . . ?
C1 C2 C3 C11 177.0(2) . . . . ?
C1 C6 C7 C8 178.2(2) . . . . ?
C2 C1 C6 C5 -2.8(3) . . . . ?
C2 C1 C6 C7 178.6(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 C14 -179.0(2) . . . . ?
C2 C3 C11 C12 179.1(2) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 C10 178.35(19) . . . . ?
C3 C4 C14 C13 -0.4(3) . . . . ?
C3 C11 C12 C13 0.3(4) . . . . ?
C4 C3 C11 C12 -1.4(4) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 179.81(19) . . . . ?
C4 C5 C10 C9 -179.74(19) . . . . ?
C5 C4 C14 C13 179.6(2) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C1 C2 O2 -176.6(2) . . . . ?
C6 C1 C2 C3 3.4(3) . . . . ?
C6 C5 C10 C9 -1.2(3) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C7 C8 C9 C15 -177.5(2) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C10 C5 C6 C1 -177.40(19) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
C11 C3 C4 C5 -178.61(19) . . . . ?
C11 C3 C4 C14 1.4(3) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C4 -0.7(4) . . . . ?
C14 C4 C5 C6 179.8(2) . . . . ?
C14 C4 C5 C10 -1.7(3) . . . . ?
C15 C9 C10 C5 178.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
