# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_DCH80_20221122
_database_code_depnum_ccdc_archive 'CCDC 2261197'
loop_
_audit_author_name
_audit_author_address
'Daphaulide F'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2023-05-07 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         248.31
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.70780(10)
_cell_length_b                   14.4353(4)
_cell_length_c                   16.4245(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1353.28(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7554
_cell_measurement_theta_min      4.0772
_cell_measurement_theta_max      68.3755
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9069
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         68.37
_diffrn_reflns_theta_full        68.37
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             2470
_reflns_number_gt                2414
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0685
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_number_reflns         2470
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.1518P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.146
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9283(3) 0.60868(9) 0.57925(9) 0.0485(4) Uani d . . . 1 . .
O O2 0.07456(19) 0.32978(8) 0.39760(7) 0.0309(3) Uani d . . . 1 . .
O O3 0.71218(19) 0.48686(8) 0.54146(7) 0.0302(3) Uani d . . . 1 . .
C C1 0.7187(3) 0.70099(11) 0.43415(11) 0.0347(4) Uani d . . . 1 . .
H H3 0.85063 0.733074 0.455368 0.042 Uiso calc U . R 1 . .
H H1 0.631786 0.726853 0.390385 0.042 Uiso calc U . R 1 . .
C C2 0.6562(3) 0.62037(10) 0.46554(9) 0.0271(3) Uani d . . . 1 . .
C C3 0.4602(3) 0.55535(10) 0.44423(8) 0.0243(3) Uani d . . . 1 . .
H H4 0.326325 0.569478 0.481507 0.029 Uiso calc U . R 1 . .
C C4 0.3657(3) 0.55683(10) 0.35759(9) 0.0250(3) Uani d . . . 1 . .
H H8 0.490899 0.537337 0.319546 0.03 Uiso calc U . R 1 . .
H H7 0.31927 0.620857 0.343242 0.03 Uiso calc U . R 1 . .
C C5 0.1539(2) 0.49232(10) 0.34790(8) 0.0240(3) Uani d . . . 1 . .
H H6 0.040961 0.503865 0.393337 0.029 Uiso calc U . R 1 . .
C C6 0.0243(3) 0.50217(11) 0.26544(9) 0.0296(3) Uani d . . . 1 . .
H H15 -0.130459 0.470325 0.27098 0.036 Uiso calc U . R 1 . .
C C7 0.1746(4) 0.44413(12) 0.20749(10) 0.0365(4) Uani d . . . 1 . .
H H2 0.312073 0.47989 0.188464 0.044 Uiso calc U . R 1 . .
H H12 0.082188 0.424154 0.159595 0.044 Uiso calc U . R 1 . .
C C8 0.7844(3) 0.57577(11) 0.53416(10) 0.0309(3) Uani d . . . 1 . .
C C9 0.5654(3) 0.46279(10) 0.47142(9) 0.0240(3) Uani d . . . 1 . .
H H5 0.667995 0.438531 0.426912 0.029 Uiso calc U . R 1 . .
C C10 0.3875(3) 0.38886(10) 0.49372(9) 0.0278(3) Uani d . . . 1 . .
H H20 0.246664 0.417645 0.518193 0.033 Uiso calc U . R 1 . .
H H19 0.455532 0.345088 0.533639 0.033 Uiso calc U . R 1 . .
C C11 0.3225(3) 0.33814(10) 0.41577(9) 0.0269(3) Uani d . . . 1 . .
C C12 0.2202(3) 0.38972(10) 0.34686(9) 0.0253(3) Uani d . . . 1 . .
C C13 -0.0230(3) 0.60017(12) 0.23578(10) 0.0382(4) Uani d . . . 1 . .
H H10 0.125734 0.630591 0.222658 0.057 Uiso calc U . R 1 . .
H H9 -0.103606 0.635169 0.278564 0.057 Uiso calc U . R 1 . .
H H11 -0.12178 0.597926 0.187009 0.057 Uiso calc U . R 1 . .
C C14 0.2517(3) 0.36042(11) 0.25814(10) 0.0334(4) Uani d . . . 1 . .
H H13 0.153459 0.305749 0.245566 0.04 Uiso calc U . R 1 . .
H H14 0.417531 0.344861 0.246921 0.04 Uiso calc U . R 1 . .
C C15 0.4642(3) 0.25194(11) 0.40048(11) 0.0345(4) Uani d . . . 1 . .
H H16 0.439225 0.207909 0.445059 0.052 Uiso calc U . R 1 . .
H H17 0.630771 0.268071 0.397448 0.052 Uiso calc U . R 1 . .
H H18 0.414932 0.223721 0.34899 0.052 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.204(2) ?
O2 C11 . 1.4514(18) ?
O2 C12 . 1.4610(18) ?
O3 C8 . 1.353(2) ?
O3 C9 . 1.4650(18) ?
C1 C2 . 1.322(2) ?
C1 H3 . 0.95 ?
C1 H1 . 0.95 ?
C2 C8 . 1.490(2) ?
C2 C3 . 1.502(2) ?
C3 C4 . 1.522(2) ?
C3 C9 . 1.5314(19) ?
C3 H4 . 1.0 ?
C4 C5 . 1.535(2) ?
C4 H8 . 0.99 ?
C4 H7 . 0.99 ?
C5 C12 . 1.529(2) ?
C5 C6 . 1.5497(19) ?
C5 H6 . 1.0 ?
C6 C13 . 1.520(2) ?
C6 C7 . 1.531(2) ?
C6 H15 . 1.0 ?
C7 C14 . 1.532(2) ?
C7 H2 . 0.99 ?
C7 H12 . 0.99 ?
C9 C10 . 1.518(2) ?
C9 H5 . 1.0 ?
C10 C11 . 1.521(2) ?
C10 H20 . 0.99 ?
C10 H19 . 0.99 ?
C11 C12 . 1.475(2) ?
C11 C15 . 1.505(2) ?
C12 C14 . 1.528(2) ?
C13 H10 . 0.98 ?
C13 H9 . 0.98 ?
C13 H11 . 0.98 ?
C14 H13 . 0.99 ?
C14 H14 . 0.99 ?
C15 H16 . 0.98 ?
C15 H17 . 0.98 ?
C15 H18 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O2 C12 . . 60.87(9) ?
C8 O3 C9 . . 109.23(12) ?
C2 C1 H3 . . 120.0 ?
C2 C1 H1 . . 120.0 ?
H3 C1 H1 . . 120.0 ?
C1 C2 C8 . . 122.89(15) ?
C1 C2 C3 . . 131.33(15) ?
C8 C2 C3 . . 105.78(13) ?
C2 C3 C4 . . 118.23(12) ?
C2 C3 C9 . . 100.67(11) ?
C4 C3 C9 . . 115.08(11) ?
C2 C3 H4 . . 107.4 ?
C4 C3 H4 . . 107.4 ?
C9 C3 H4 . . 107.4 ?
C3 C4 C5 . . 111.57(11) ?
C3 C4 H8 . . 109.3 ?
C5 C4 H8 . . 109.3 ?
C3 C4 H7 . . 109.3 ?
C5 C4 H7 . . 109.3 ?
H8 C4 H7 . . 108.0 ?
C12 C5 C4 . . 113.20(12) ?
C12 C5 C6 . . 101.37(11) ?
C4 C5 C6 . . 114.27(12) ?
C12 C5 H6 . . 109.2 ?
C4 C5 H6 . . 109.2 ?
C6 C5 H6 . . 109.2 ?
C13 C6 C7 . . 114.19(14) ?
C13 C6 C5 . . 116.76(13) ?
C7 C6 C5 . . 103.05(12) ?
C13 C6 H15 . . 107.4 ?
C7 C6 H15 . . 107.4 ?
C5 C6 H15 . . 107.4 ?
C6 C7 C14 . . 104.79(13) ?
C6 C7 H2 . . 110.8 ?
C14 C7 H2 . . 110.8 ?
C6 C7 H12 . . 110.8 ?
C14 C7 H12 . . 110.8 ?
H2 C7 H12 . . 108.9 ?
O1 C8 O3 . . 121.84(16) ?
O1 C8 C2 . . 129.04(15) ?
O3 C8 C2 . . 109.12(13) ?
O3 C9 C10 . . 111.09(11) ?
O3 C9 C3 . . 104.26(11) ?
C10 C9 C3 . . 114.92(12) ?
O3 C9 H5 . . 108.8 ?
C10 C9 H5 . . 108.8 ?
C3 C9 H5 . . 108.8 ?
C9 C10 C11 . . 107.36(12) ?
C9 C10 H20 . . 110.2 ?
C11 C10 H20 . . 110.2 ?
C9 C10 H19 . . 110.2 ?
C11 C10 H19 . . 110.2 ?
H20 C10 H19 . . 108.5 ?
O2 C11 C12 . . 59.89(9) ?
O2 C11 C15 . . 114.89(12) ?
C12 C11 C15 . . 120.12(14) ?
O2 C11 C10 . . 116.80(13) ?
C12 C11 C10 . . 119.97(13) ?
C15 C11 C10 . . 114.04(13) ?
O2 C12 C11 . . 59.25(9) ?
O2 C12 C14 . . 116.56(12) ?
C11 C12 C14 . . 123.06(13) ?
O2 C12 C5 . . 115.24(12) ?
C11 C12 C5 . . 125.33(13) ?
C14 C12 C5 . . 107.94(12) ?
C6 C13 H10 . . 109.5 ?
C6 C13 H9 . . 109.5 ?
H10 C13 H9 . . 109.5 ?
C6 C13 H11 . . 109.5 ?
H10 C13 H11 . . 109.5 ?
H9 C13 H11 . . 109.5 ?
C12 C14 C7 . . 105.41(12) ?
C12 C14 H13 . . 110.7 ?
C7 C14 H13 . . 110.7 ?
C12 C14 H14 . . 110.7 ?
C7 C14 H14 . . 110.7 ?
H13 C14 H14 . . 108.8 ?
C11 C15 H16 . . 109.5 ?
C11 C15 H17 . . 109.5 ?
H16 C15 H17 . . 109.5 ?
C11 C15 H18 . . 109.5 ?
H16 C15 H18 . . 109.5 ?
H17 C15 H18 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . 26.2(2) ?
C8 C2 C3 C4 . . . . -153.48(13) ?
C1 C2 C3 C9 . . . . 152.36(17) ?
C8 C2 C3 C9 . . . . -27.28(14) ?
C2 C3 C4 C5 . . . . -175.35(12) ?
C9 C3 C4 C5 . . . . 65.75(16) ?
C3 C4 C5 C12 . . . . -74.00(15) ?
C3 C4 C5 C6 . . . . 170.62(11) ?
C12 C5 C6 C13 . . . . -167.03(14) ?
C4 C5 C6 C13 . . . . -44.92(18) ?
C12 C5 C6 C7 . . . . -41.02(15) ?
C4 C5 C6 C7 . . . . 81.08(16) ?
C13 C6 C7 C14 . . . . 165.68(14) ?
C5 C6 C7 C14 . . . . 38.04(17) ?
C9 O3 C8 O1 . . . . -171.47(16) ?
C9 O3 C8 C2 . . . . 9.38(16) ?
C1 C2 C8 O1 . . . . 13.7(3) ?
C3 C2 C8 O1 . . . . -166.63(18) ?
C1 C2 C8 O3 . . . . -167.25(15) ?
C3 C2 C8 O3 . . . . 12.43(16) ?
C8 O3 C9 C10 . . . . -151.37(13) ?
C8 O3 C9 C3 . . . . -27.04(15) ?
C2 C3 C9 O3 . . . . 32.54(13) ?
C4 C3 C9 O3 . . . . 160.82(12) ?
C2 C3 C9 C10 . . . . 154.38(13) ?
C4 C3 C9 C10 . . . . -77.34(16) ?
O3 C9 C10 C11 . . . . -155.04(12) ?
C3 C9 C10 C11 . . . . 86.90(15) ?
C12 O2 C11 C15 . . . . -111.75(15) ?
C12 O2 C11 C10 . . . . 110.73(14) ?
C9 C10 C11 O2 . . . . -128.19(13) ?
C9 C10 C11 C12 . . . . -59.14(17) ?
C9 C10 C11 C15 . . . . 93.94(15) ?
C11 O2 C12 C14 . . . . 114.34(15) ?
C11 O2 C12 C5 . . . . -117.61(15) ?
C15 C11 C12 O2 . . . . 103.06(15) ?
C10 C11 C12 O2 . . . . -105.50(15) ?
O2 C11 C12 C14 . . . . -103.51(15) ?
C15 C11 C12 C14 . . . . -0.4(2) ?
C10 C11 C12 C14 . . . . 150.99(15) ?
O2 C11 C12 C5 . . . . 100.75(15) ?
C15 C11 C12 C5 . . . . -156.19(14) ?
C10 C11 C12 C5 . . . . -4.8(2) ?
C4 C5 C12 O2 . . . . 134.30(13) ?
C6 C5 C12 O2 . . . . -102.86(13) ?
C4 C5 C12 C11 . . . . 65.32(18) ?
C6 C5 C12 C11 . . . . -171.83(13) ?
C4 C5 C12 C14 . . . . -93.46(14) ?
C6 C5 C12 C14 . . . . 29.39(15) ?
O2 C12 C14 C7 . . . . 125.00(15) ?
C11 C12 C14 C7 . . . . -165.89(15) ?
C5 C12 C14 C7 . . . . -6.52(17) ?
C6 C7 C14 C12 . . . . -19.58(18) ?

