# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1971464'
loop_
_audit_author_name
_audit_author_address
'Qifeng Wang'
;Jilin University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-11-19 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            'C28 H16 O3'
_chemical_formula_weight         400.41

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      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   8.6460(10)
_cell_length_b                   9.6188(11)
_cell_length_c                   12.4676(14)
_cell_angle_alpha                98.358(2)
_cell_angle_beta                 108.221(2)
_cell_angle_gamma                99.589(2)
_cell_volume                     949.28(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    711
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      21.1

_exptl_crystal_description       column
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            6958
_diffrn_reflns_av_unetI/netI     0.1437
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.759
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4561
_reflns_number_gt                1657
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0981P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4561
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1648
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.2225
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_restrained_S_all      0.843
_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
C1 C 0.2968(4) 0.2910(4) 0.0832(3) 0.0387(8) Uani 1 1 d . . . . .
C2 C 0.4655(4) 0.3317(4) 0.0724(3) 0.0377(8) Uani 1 1 d . . . . .
C3 C 0.5781(5) 0.4540(4) 0.1432(3) 0.0548(11) Uani 1 1 d . . . . .
H3 H 0.544904 0.516049 0.191750 0.066 Uiso 1 1 calc R U . . .
C4 C 0.7406(5) 0.4858(4) 0.1432(3) 0.0578(11) Uani 1 1 d . . . . .
H4 H 0.816759 0.568107 0.191846 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7873(5) 0.3939(5) 0.0701(3) 0.0552(11) Uani 1 1 d . . . . .
H5 H 0.896462 0.413133 0.070380 0.066 Uiso 1 1 calc R U . . .
C6 C 0.6752(5) 0.2751(4) -0.0025(3) 0.0440(9) Uani 1 1 d . . . . .
H6 H 0.708993 0.215038 -0.051932 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5106(4) 0.2407(4) -0.0048(3) 0.0366(8) Uani 1 1 d . . . . .
C8 C 0.3865(4) 0.1136(4) -0.0868(3) 0.0371(8) Uani 1 1 d . . . . .
C9 C 0.4295(5) 0.0150(4) -0.1587(3) 0.0429(9) Uani 1 1 d . . . . .
H9 H 0.540448 0.026950 -0.154406 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3114(5) -0.1009(4) -0.2368(3) 0.0571(11) Uani 1 1 d . . . . .
H10 H 0.343659 -0.165281 -0.284195 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1458(5) -0.1215(5) -0.2447(4) 0.0605(11) Uani 1 1 d . . . . .
H11 H 0.066647 -0.199837 -0.296689 0.073 Uiso 1 1 calc R U . . .
C12 C 0.0994(5) -0.0251(4) -0.1750(3) 0.0516(10) Uani 1 1 d . . . . .
H12 H -0.012075 -0.037681 -0.180679 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2173(4) 0.0913(4) -0.0961(3) 0.0390(8) Uani 1 1 d . . . . .
C14 C 0.1627(5) 0.1921(4) -0.0223(3) 0.0447(9) Uani 1 1 d . . . . .
C15 C 0.2483(4) 0.4190(4) 0.2314(3) 0.0382(8) Uani 1 1 d . . . . .
C16 C 0.2909(4) 0.3008(4) 0.2655(3) 0.0382(8) Uani 1 1 d . . . . .
C17 C 0.3036(4) 0.2726(4) 0.3740(3) 0.0386(8) Uani 1 1 d . . . . .
C18 C 0.3476(5) 0.1479(4) 0.4103(3) 0.0475(10) Uani 1 1 d . . . . .
H18 H 0.369714 0.078313 0.360555 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3577(5) 0.1295(5) 0.5198(3) 0.0617(12) Uani 1 1 d . . . . .
H19 H 0.390202 0.048946 0.544793 0.074 Uiso 1 1 calc R U . . .
C20 C 0.3200(6) 0.2296(5) 0.5917(4) 0.0670(13) Uani 1 1 d . . . . .
H20 H 0.323043 0.214491 0.664275 0.080 Uiso 1 1 calc R U . . .
C21 C 0.2780(5) 0.3516(4) 0.5583(3) 0.0580(11) Uani 1 1 d . . . . .
H21 H 0.254145 0.417990 0.609448 0.070 Uiso 1 1 calc R U . . .
C22 C 0.2698(4) 0.3798(4) 0.4510(3) 0.0420(9) Uani 1 1 d . . . . .
C23 C 0.2246(4) 0.5088(4) 0.4146(3) 0.0427(9) Uani 1 1 d . . . . .
C24 C 0.1850(5) 0.6150(4) 0.4817(3) 0.0556(11) Uani 1 1 d . . . . .
H24 H 0.187679 0.605128 0.555361 0.067 Uiso 1 1 calc R U . . .
C25 C 0.1420(5) 0.7339(4) 0.4435(3) 0.0587(11) Uani 1 1 d . . . . .
H25 H 0.114713 0.802014 0.491279 0.070 Uiso 1 1 calc R U . . .
C26 C 0.1379(5) 0.7555(4) 0.3367(4) 0.0584(11) Uani 1 1 d . . . . .
H26 H 0.111556 0.838682 0.313131 0.070 Uiso 1 1 calc R U . . .
C27 C 0.1731(4) 0.6534(4) 0.2649(3) 0.0465(9) Uani 1 1 d . . . . .
H27 H 0.169718 0.666629 0.191858 0.056 Uiso 1 1 calc R U . . .
C28 C 0.2144(4) 0.5286(4) 0.3012(3) 0.0382(8) Uani 1 1 d . . . . .
O1 O 0.3131(3) 0.2101(2) 0.1769(2) 0.0457(7) Uani 1 1 d . . . . .
O2 O 0.2408(3) 0.4161(3) 0.1187(2) 0.0471(7) Uani 1 1 d . . . . .
O3 O 0.0164(3) 0.1942(3) -0.0414(2) 0.0673(9) Uani 1 1 d . . . . .


_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
C1 O2 1.432(4) . ?
C1 O1 1.479(4) . ?
C1 C2 1.500(5) . ?
C1 C14 1.515(5) . ?
C2 C3 1.375(5) . ?
C2 C7 1.396(4) . ?
C3 C4 1.388(5) . ?
C4 C5 1.375(5) . ?
C5 C6 1.359(5) . ?
C6 C7 1.396(5) . ?
C7 C8 1.484(5) . ?
C8 C9 1.386(4) . ?
C8 C13 1.408(5) . ?
C9 C10 1.385(5) . ?
C10 C11 1.382(5) . ?
C11 C12 1.372(5) . ?
C12 C13 1.390(5) . ?
C13 C14 1.474(5) . ?
C14 O3 1.216(4) . ?
C15 C16 1.338(4) . ?
C15 O2 1.382(4) . ?
C15 C28 1.397(4) . ?
C16 O1 1.387(4) . ?
C16 C17 1.393(4) . ?
C17 C18 1.410(4) . ?
C17 C22 1.435(4) . ?
C18 C19 1.380(5) . ?
C19 C20 1.369(5) . ?
C20 C21 1.368(5) . ?
C21 C22 1.386(5) . ?
C22 C23 1.454(5) . ?
C23 C24 1.382(5) . ?
C23 C28 1.431(4) . ?
C24 C25 1.365(5) . ?
C25 C26 1.368(5) . ?
C26 C27 1.369(5) . ?
C27 C28 1.404(4) . ?

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
O2 C1 O1 105.8(2) . . ?
O2 C1 C2 111.3(3) . . ?
O1 C1 C2 108.0(3) . . ?
O2 C1 C14 110.5(3) . . ?
O1 C1 C14 105.4(3) . . ?
C2 C1 C14 115.3(3) . . ?
C3 C2 C7 120.5(3) . . ?
C3 C2 C1 119.7(3) . . ?
C7 C2 C1 119.7(3) . . ?
C2 C3 C4 120.7(4) . . ?
C5 C4 C3 119.0(4) . . ?
C6 C5 C4 120.5(4) . . ?
C5 C6 C7 121.8(3) . . ?
C2 C7 C6 117.4(3) . . ?
C2 C7 C8 120.7(3) . . ?
C6 C7 C8 121.8(3) . . ?
C9 C8 C13 117.3(3) . . ?
C9 C8 C7 122.3(3) . . ?
C13 C8 C7 120.3(3) . . ?
C10 C9 C8 121.6(3) . . ?
C11 C10 C9 120.4(4) . . ?
C12 C11 C10 119.3(4) . . ?
C11 C12 C13 120.7(4) . . ?
C12 C13 C8 120.7(3) . . ?
C12 C13 C14 119.1(3) . . ?
C8 C13 C14 120.2(3) . . ?
O3 C14 C13 122.5(4) . . ?
O3 C14 C1 120.2(3) . . ?
C13 C14 C1 117.2(3) . . ?
C16 C15 O2 110.9(3) . . ?
C16 C15 C28 123.8(3) . . ?
O2 C15 C28 125.3(3) . . ?
C15 C16 O1 110.7(3) . . ?
C15 C16 C17 123.6(3) . . ?
O1 C16 C17 125.6(3) . . ?
C16 C17 C18 123.9(3) . . ?
C16 C17 C22 116.1(3) . . ?
C18 C17 C22 120.0(3) . . ?
C19 C18 C17 119.8(4) . . ?
C20 C19 C18 120.2(4) . . ?
C21 C20 C19 120.9(4) . . ?
C20 C21 C22 122.4(4) . . ?
C21 C22 C17 116.8(3) . . ?
C21 C22 C23 122.8(3) . . ?
C17 C22 C23 120.4(3) . . ?
C24 C23 C28 116.3(3) . . ?
C24 C23 C22 124.2(3) . . ?
C28 C23 C22 119.5(3) . . ?
C25 C24 C23 122.1(4) . . ?
C24 C25 C26 121.7(4) . . ?
C25 C26 C27 119.2(3) . . ?
C26 C27 C28 120.2(3) . . ?
C15 C28 C27 123.1(3) . . ?
C15 C28 C23 116.5(3) . . ?
C27 C28 C23 120.4(3) . . ?
C16 O1 C1 105.2(2) . . ?
C15 O2 C1 106.7(2) . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.067



