# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc26x0x2
_database_code_depnum_ccdc_archive 'CCDC 2052724'
loop_
_audit_author_name
_audit_author_address
aaa
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-12-28 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0451(17)
_cell_length_b                   7.3918(17)
_cell_length_c                   12.782(3)
_cell_angle_alpha                76.201(3)
_cell_angle_beta                 81.124(3)
_cell_angle_gamma                73.395(3)
_cell_volume                     616.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6292
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2159
_reflns_number_gt                1918
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0703P)²+0.1220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.30(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2159
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58702(13) 0.40300(14) 0.32350(8) 0.0452(3) Uani 1 1 d . . .
O2 O 0.85798(15) 0.27584(17) 0.40806(9) 0.0591(4) Uani 1 1 d . . .
O3 O 0.59993(16) -0.05246(16) 0.78640(8) 0.0553(3) Uani 1 1 d . . .
C1 C 0.8066(3) -0.0897(3) 0.79660(14) 0.0618(5) Uani 1 1 d . . .
H1A H 0.8366 -0.1679 0.8666 0.093 Uiso 1 1 calc R . .
H1B H 0.8403 0.0302 0.7885 0.093 Uiso 1 1 calc R . .
H1C H 0.8821 -0.1564 0.7416 0.093 Uiso 1 1 calc R . .
C2 C 0.5303(2) 0.05614(19) 0.69162(11) 0.0433(4) Uani 1 1 d . . .
C3 C 0.3249(2) 0.0967(2) 0.68740(12) 0.0485(4) Uani 1 1 d . . .
H3A H 0.2468 0.0511 0.7479 0.058 Uiso 1 1 calc R . .
C4 C 0.2364(2) 0.2022(2) 0.59603(11) 0.0464(4) Uani 1 1 d . . .
H4A H 0.0996 0.2271 0.5950 0.056 Uiso 1 1 calc R . .
C5 C 0.35142(19) 0.27309(18) 0.50372(11) 0.0375(3) Uani 1 1 d . . .
C6 C 0.2680(2) 0.38210(19) 0.40521(11) 0.0413(4) Uani 1 1 d . . .
H6A H 0.1314 0.4111 0.4015 0.050 Uiso 1 1 calc R . .
C7 C 0.38415(19) 0.44254(18) 0.31865(11) 0.0393(3) Uani 1 1 d . . .
C8 C 0.6803(2) 0.30139(19) 0.41413(11) 0.0415(3) Uani 1 1 d . . .
C9 C 0.55598(19) 0.23244(18) 0.50913(10) 0.0373(3) Uani 1 1 d . . .
C10 C 0.6467(2) 0.12408(19) 0.60220(11) 0.0415(4) Uani 1 1 d . . .
H10A H 0.7835 0.0982 0.6038 0.050 Uiso 1 1 calc R . .
C11 C 0.3228(2) 0.55227(19) 0.21170(11) 0.0434(4) Uani 1 1 d . . .
C12 C 0.1296(2) 0.5827(2) 0.18610(13) 0.0558(4) Uani 1 1 d . . .
H12A H 0.0383 0.5331 0.2371 0.067 Uiso 1 1 calc R . .
C13 C 0.0720(3) 0.6858(3) 0.08575(15) 0.0703(5) Uani 1 1 d . . .
H13A H -0.0575 0.7053 0.0697 0.084 Uiso 1 1 calc R . .
C14 C 0.2059(3) 0.7597(3) 0.00954(14) 0.0747(6) Uani 1 1 d . . .
H14A H 0.1671 0.8286 -0.0581 0.090 Uiso 1 1 calc R . .
C15 C 0.3953(3) 0.7315(3) 0.03349(14) 0.0736(6) Uani 1 1 d . . .
H15A H 0.4853 0.7821 -0.0180 0.088 Uiso 1 1 calc R . .
C16 C 0.4556(3) 0.6282(2) 0.13393(13) 0.0575(4) Uani 1 1 d . . .
H16A H 0.5855 0.6098 0.1492 0.069 Uiso 1 1 calc R . .


_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 C8 1.3695(17) . ?
O1 C7 1.3827(16) . ?
O2 C8 1.2043(17) . ?
O3 C2 1.3592(17) . ?
O3 C1 1.423(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C10 1.3799(19) . ?
C2 C3 1.398(2) . ?
C3 C4 1.369(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.4055(19) . ?
C4 H4A 0.9300 . ?
C5 C9 1.3948(19) . ?
C5 C6 1.4332(19) . ?
C6 C7 1.3369(19) . ?
C6 H6A 0.9300 . ?
C7 C11 1.4719(19) . ?
C8 C9 1.4606(18) . ?
C9 C10 1.3974(19) . ?
C10 H10A 0.9300 . ?
C11 C16 1.388(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.381(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.362(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.388(2) . ?
C15 H15A 0.9300 . ?
C16 H16A 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
C8 O1 C7 123.27(10) . . ?
C2 O3 C1 117.68(12) . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 C10 124.87(13) . . ?
O3 C2 C3 115.57(12) . . ?
C10 C2 C3 119.56(13) . . ?
C4 C3 C2 121.35(13) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 120.31(13) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C9 C5 C4 117.79(13) . . ?
C9 C5 C6 119.26(12) . . ?
C4 C5 C6 122.95(13) . . ?
C7 C6 C5 120.75(13) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 O1 120.29(12) . . ?
C6 C7 C11 127.46(13) . . ?
O1 C7 C11 112.25(11) . . ?
O2 C8 O1 116.97(12) . . ?
O2 C8 C9 125.83(13) . . ?
O1 C8 C9 117.20(12) . . ?
C5 C9 C10 121.99(12) . . ?
C5 C9 C8 119.22(12) . . ?
C10 C9 C8 118.78(12) . . ?
C2 C10 C9 119.00(13) . . ?
C2 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C16 C11 C12 118.31(14) . . ?
C16 C11 C7 120.96(14) . . ?
C12 C11 C7 120.74(13) . . ?
C13 C12 C11 120.73(16) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C14 C13 C12 120.17(18) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 119.79(16) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.77(17) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C11 C16 C15 120.23(17) . . ?
C11 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?

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
C1 O3 C2 C10 3.9(2) . . . . ?
C1 O3 C2 C3 -176.96(12) . . . . ?
O3 C2 C3 C4 -178.99(12) . . . . ?
C10 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C9 -0.1(2) . . . . ?
C3 C4 C5 C6 179.13(12) . . . . ?
C9 C5 C6 C7 0.9(2) . . . . ?
C4 C5 C6 C7 -178.39(13) . . . . ?
C5 C6 C7 O1 -1.0(2) . . . . ?
C5 C6 C7 C11 178.91(12) . . . . ?
C8 O1 C7 C6 0.43(19) . . . . ?
C8 O1 C7 C11 -179.47(11) . . . . ?
C7 O1 C8 O2 179.76(12) . . . . ?
C7 O1 C8 C9 0.22(18) . . . . ?
C4 C5 C9 C10 0.4(2) . . . . ?
C6 C5 C9 C10 -178.89(11) . . . . ?
C4 C5 C9 C8 179.08(12) . . . . ?
C6 C5 C9 C8 -0.22(19) . . . . ?
O2 C8 C9 C5 -179.80(13) . . . . ?
O1 C8 C9 C5 -0.30(18) . . . . ?
O2 C8 C9 C10 -1.1(2) . . . . ?
O1 C8 C9 C10 178.41(11) . . . . ?
O3 C2 C10 C9 179.18(12) . . . . ?
C3 C2 C10 C9 0.0(2) . . . . ?
C5 C9 C10 C2 -0.4(2) . . . . ?
C8 C9 C10 C2 -179.03(11) . . . . ?
C6 C7 C11 C16 171.03(14) . . . . ?
O1 C7 C11 C16 -9.08(19) . . . . ?
C6 C7 C11 C12 -8.9(2) . . . . ?
O1 C7 C11 C12 171.02(12) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C7 C11 C12 C13 179.96(14) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C7 C11 C16 C15 -179.94(14) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066
