# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_RuiGuo082020
_database_code_depnum_ccdc_archive 'CCDC 2179035'
loop_
_audit_author_name
_audit_author_address
'Steven J. Geib'
;University of Pittsburgh
United States of America
;
_audit_update_record             
;
2022-06-14 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         348.42

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   8.3486(2)
_cell_length_b                   10.8563(2)
_cell_length_c                   11.6441(2)
_cell_angle_alpha                62.4089(9)
_cell_angle_beta                 80.6019(9)
_cell_angle_gamma                88.2485(10)
_cell_volume                     921.56(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7868
_cell_measurement_theta_min      4.346
_cell_measurement_theta_max      68.154
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.025
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372

_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'

_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Bruker X8 Prospector Ultra IMuS'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            15722
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_theta_min         4.35
_diffrn_reflns_theta_max         68.29
_diffrn_reflns_theta_full        68.29
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3290
_reflns_number_gt                3010
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1221
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_number_reflns         3290
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0737P)²+0.1773P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0089(12)

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       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_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 0.46961(11) 0.48762(9) 0.17573(9) 0.0275(2) Uani d . . . 1 . .
C C1 0.13886(15) 0.30453(13) 0.26446(11) 0.0204(3) Uani d . . . 1 . .
O O2 0.31871(12) 1.25204(10) -0.24668(9) 0.0311(3) Uani d . . . 1 . .
C C2 0.03388(15) 0.35497(13) 0.17183(12) 0.0228(3) Uani d . . . 1 . .
H H2 -0.010(2) 0.4485(18) 0.1492(16) 0.029(4) Uiso d . . . 1 . .
O O3 0.55034(11) 1.19596(9) -0.33720(9) 0.0276(3) Uani d . . . 1 . .
C C3 -0.00881(17) 0.27657(14) 0.11436(12) 0.0262(3) Uani d . . . 1 . .
H H3 -0.081(2) 0.3135(19) 0.0522(19) 0.038(4) Uiso d . . . 1 . .
C C4 0.05542(17) 0.14752(14) 0.14744(13) 0.0270(3) Uani d . . . 1 . .
H H4 0.0220(18) 0.0902(16) 0.1091(15) 0.025(4) Uiso d . . . 1 . .
C C5 0.16323(16) 0.09773(14) 0.23643(12) 0.0253(3) Uani d . . . 1 . .
H H5 0.213(2) 0.0061(19) 0.2606(17) 0.032(4) Uiso d . . . 1 . .
C C6 0.20618(15) 0.17453(13) 0.29628(12) 0.0220(3) Uani d . . . 1 . .
C C7 0.32535(17) 0.12198(15) 0.39134(13) 0.0274(3) Uani d . . . 1 . .
H H7A 0.407(2) 0.2021(17) 0.3669(16) 0.029(4) Uiso d . . . 1 . .
H H7B 0.383(2) 0.0459(19) 0.3819(18) 0.037(4) Uiso d . . . 1 . .
C C8 0.24599(18) 0.07477(15) 0.53526(13) 0.0300(3) Uani d . . . 1 . .
H H8A 0.194(2) -0.0189(19) 0.5740(17) 0.034(4) Uiso d . . . 1 . .
H H8B 0.332(2) 0.067(2) 0.588(2) 0.045(5) Uiso d . . . 1 . .
C C9 0.11838(17) 0.17467(14) 0.54870(12) 0.0268(3) Uani d . . . 1 . .
H H9B 0.0956(19) 0.1558(16) 0.6408(17) 0.026(4) Uiso d . . . 1 . .
H H9A 0.015(2) 0.1530(18) 0.5257(17) 0.035(4) Uiso d . . . 1 . .
C C10 0.16506(15) 0.32679(13) 0.46130(12) 0.0231(3) Uani d . . . 1 . .
H H10 0.1868(19) 0.3837(17) 0.5034(16) 0.025(4) Uiso d . . . 1 . .
C C11 0.17329(14) 0.38721(13) 0.33105(12) 0.0207(3) Uani d . . . 1 . .
C C12 0.20879(15) 0.53965(13) 0.24479(12) 0.0207(3) Uani d . . . 1 . .
C C13 0.09438(16) 0.63682(14) 0.23949(12) 0.0236(3) Uani d . . . 1 . .
H H13 -0.010(2) 0.6081(17) 0.2964(17) 0.029(4) Uiso d . . . 1 . .
C C14 0.12414(16) 0.77709(14) 0.14966(12) 0.0237(3) Uani d . . . 1 . .
H H14 0.043(2) 0.8411(18) 0.1460(16) 0.028(4) Uiso d . . . 1 . .
C C15 0.26986(15) 0.82295(13) 0.06169(12) 0.0217(3) Uani d . . . 1 . .
C C16 0.38987(15) 0.72669(13) 0.06958(12) 0.0224(3) Uani d . . . 1 . .
H H16] 0.495(2) 0.7549(17) 0.0110(17) 0.031(4) Uiso d . . . 1 . .
C C17 0.35989(15) 0.58778(13) 0.16018(12) 0.0212(3) Uani d . . . 1 . .
C C18 0.62850(17) 0.53204(16) 0.09770(14) 0.0303(3) Uani d . . . 1 . .
H H18A 0.623(2) 0.5703(18) 0.0037(19) 0.035(4) Uiso d . . . 1 . .
H H18B 0.681(2) 0.6011(18) 0.1171(17) 0.033(4) Uiso d . . . 1 . .
H H18C 0.684(2) 0.443(2) 0.1243(18) 0.038(4) Uiso d . . . 1 . .
C C19 0.29245(16) 0.96809(14) -0.04086(12) 0.0234(3) Uani d . . . 1 . .
H H19 0.210(2) 1.0332(18) -0.0328(17) 0.034(4) Uiso d . . . 1 . .
C C20 0.41029(16) 1.02075(14) -0.14474(13) 0.0256(3) Uani d . . . 1 . .
H H20 0.492(2) 0.9691(19) -0.1617(18) 0.037(4) Uiso d . . . 1 . .
C C21 0.41747(16) 1.16760(13) -0.24477(12) 0.0237(3) Uani d . . . 1 . .
C C22 0.56879(18) 1.33731(14) -0.44370(14) 0.0300(3) Uani d . . . 1 . .
H H22A 0.578(2) 1.398(2) -0.4031(19) 0.041(5) Uiso d . . . 1 . .
H H22B 0.472(2) 1.3565(19) -0.4837(19) 0.041(5) Uiso d . . . 1 . .
C C23 0.7155(2) 1.34821(19) -0.53984(17) 0.0466(4) Uani d . . . 1 . .
H H23A 0.725(3) 1.443(2) -0.617(2) 0.054(6) Uiso d . . . 1 . .
H H23B 0.708(3) 1.282(2) -0.571(2) 0.054(6) Uiso d . . . 1 . .
H H23C 0.816(3) 1.324(2) -0.497(2) 0.063(6) Uiso d . . . 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 C17 . 1.3657(15) ?
O1 C18 . 1.4343(16) ?
C1 C2 . 1.4013(18) ?
C1 C6 . 1.4072(18) ?
C1 C11 . 1.4908(17) ?
O2 C21 . 1.2090(16) ?
C2 C3 . 1.3869(19) ?
C2 H2 . 0.997(17) ?
O3 C21 . 1.3445(16) ?
O3 C22 . 1.4510(15) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.950(19) ?
C4 C5 . 1.390(2) ?
C4 H4 . 0.986(16) ?
C5 C6 . 1.3956(19) ?
C5 H5 . 0.998(18) ?
C6 C7 . 1.5101(18) ?
C7 C8 . 1.5403(19) ?
C7 H7A . 1.024(17) ?
C7 H7B . 0.985(19) ?
C8 C9 . 1.5388(19) ?
C8 H8A . 0.982(18) ?
C8 H8B . 1.00(2) ?
C9 C10 . 1.5060(18) ?
C9 H9B . 0.980(17) ?
C9 H9A . 1.009(18) ?
C10 C11 . 1.3350(18) ?
C10 H10 . 0.985(16) ?
C11 C12 . 1.4929(17) ?
C12 C13 . 1.3878(18) ?
C12 C17 . 1.4116(18) ?
C13 C14 . 1.3920(18) ?
C13 H13 . 0.969(17) ?
C14 C15 . 1.3910(18) ?
C14 H14 . 0.949(17) ?
C15 C16 . 1.4076(17) ?
C15 C19 . 1.4649(18) ?
C16 C17 . 1.3831(18) ?
C16 H16] . 0.975(18) ?
C18 H18A . 0.983(19) ?
C18 H18B . 1.009(18) ?
C18 H18C . 0.994(19) ?
C19 C20 . 1.3278(19) ?
C19 H19 . 0.999(18) ?
C20 C21 . 1.4713(18) ?
C20 H20 . 0.93(2) ?
C22 C23 . 1.485(2) ?
C22 H22A . 0.98(2) ?
C22 H22B . 0.97(2) ?
C23 H23A . 1.00(2) ?
C23 H23B . 0.94(2) ?
C23 H23C . 1.01(2) ?

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
C17 O1 C18 . . 117.25(10) ?
C2 C1 C6 . . 119.49(11) ?
C2 C1 C11 . . 119.52(11) ?
C6 C1 C11 . . 120.96(11) ?
C3 C2 C1 . . 120.93(12) ?
C3 C2 H2 . . 121.2(9) ?
C1 C2 H2 . . 117.9(9) ?
C21 O3 C22 . . 115.44(10) ?
C4 C3 C2 . . 119.50(12) ?
C4 C3 H3 . . 121.6(11) ?
C2 C3 H3 . . 118.9(11) ?
C3 C4 C5 . . 120.24(12) ?
C3 C4 H4 . . 119.5(9) ?
C5 C4 H4 . . 120.2(9) ?
C4 C5 C6 . . 121.03(12) ?
C4 C5 H5 . . 121.9(10) ?
C6 C5 H5 . . 117.1(10) ?
C5 C6 C1 . . 118.76(12) ?
C5 C6 C7 . . 121.24(11) ?
C1 C6 C7 . . 119.99(12) ?
C6 C7 C8 . . 113.60(11) ?
C6 C7 H7A . . 108.2(9) ?
C8 C7 H7A . . 106.3(9) ?
C6 C7 H7B . . 108.6(11) ?
C8 C7 H7B . . 111.0(11) ?
H7A C7 H7B . . 109.1(14) ?
C9 C8 C7 . . 112.40(11) ?
C9 C8 H8A . . 108.8(10) ?
C7 C8 H8A . . 110.4(10) ?
C9 C8 H8B . . 109.6(11) ?
C7 C8 H8B . . 109.3(11) ?
H8A C8 H8B . . 106.1(15) ?
C10 C9 C8 . . 114.78(11) ?
C10 C9 H9B . . 109.8(9) ?
C8 C9 H9B . . 108.6(9) ?
C10 C9 H9A . . 107.9(10) ?
C8 C9 H9A . . 107.8(10) ?
H9B C9 H9A . . 107.8(13) ?
C11 C10 C9 . . 122.75(11) ?
C11 C10 H10 . . 119.4(9) ?
C9 C10 H10 . . 117.9(9) ?
C10 C11 C1 . . 120.74(11) ?
C10 C11 C12 . . 123.03(11) ?
C1 C11 C12 . . 116.17(10) ?
C13 C12 C17 . . 118.10(11) ?
C13 C12 C11 . . 122.12(11) ?
C17 C12 C11 . . 119.69(11) ?
C12 C13 C14 . . 121.29(12) ?
C12 C13 H13 . . 120.7(10) ?
C14 C13 H13 . . 118.0(10) ?
C15 C14 C13 . . 120.38(12) ?
C15 C14 H14 . . 119.8(10) ?
C13 C14 H14 . . 119.7(10) ?
C14 C15 C16 . . 118.98(11) ?
C14 C15 C19 . . 119.61(11) ?
C16 C15 C19 . . 121.35(11) ?
C17 C16 C15 . . 120.15(11) ?
C17 C16 H16] . . 118.3(10) ?
C15 C16 H16] . . 121.6(10) ?
O1 C17 C16 . . 124.15(11) ?
O1 C17 C12 . . 114.90(11) ?
C16 C17 C12 . . 120.95(11) ?
O1 C18 H18A . . 110.8(10) ?
O1 C18 H18B . . 110.1(10) ?
H18A C18 H18B . . 111.8(14) ?
O1 C18 H18C . . 102.7(10) ?
H18A C18 H18C . . 107.3(15) ?
H18B C18 H18C . . 113.8(14) ?
C20 C19 C15 . . 126.37(12) ?
C20 C19 H19 . . 116.9(10) ?
C15 C19 H19 . . 116.7(10) ?
C19 C20 C21 . . 121.74(12) ?
C19 C20 H20 . . 123.7(11) ?
C21 C20 H20 . . 114.5(11) ?
O2 C21 O3 . . 123.81(12) ?
O2 C21 C20 . . 125.98(12) ?
O3 C21 C20 . . 110.21(11) ?
O3 C22 C23 . . 108.30(12) ?
O3 C22 H22A . . 106.2(11) ?
C23 C22 H22A . . 112.7(11) ?
O3 C22 H22B . . 108.1(11) ?
C23 C22 H22B . . 111.2(11) ?
H22A C22 H22B . . 110.2(15) ?
C22 C23 H23A . . 109.1(12) ?
C22 C23 H23B . . 111.0(13) ?
H23A C23 H23B . . 108.1(18) ?
C22 C23 H23C . . 111.3(13) ?
H23A C23 H23C . . 113.1(17) ?
H23B C23 H23C . . 104.2(18) ?

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
C6 C1 C2 C3 . . . . 2.16(18) ?
C11 C1 C2 C3 . . . . -175.85(11) ?
C1 C2 C3 C4 . . . . -1.07(19) ?
C2 C3 C4 C5 . . . . -0.7(2) ?
C3 C4 C5 C6 . . . . 1.43(19) ?
C4 C5 C6 C1 . . . . -0.33(18) ?
C4 C5 C6 C7 . . . . -178.99(11) ?
C2 C1 C6 C5 . . . . -1.43(17) ?
C11 C1 C6 C5 . . . . 176.55(10) ?
C2 C1 C6 C7 . . . . 177.24(11) ?
C11 C1 C6 C7 . . . . -4.78(17) ?
C5 C6 C7 C8 . . . . -108.66(14) ?
C1 C6 C7 C8 . . . . 72.70(16) ?
C6 C7 C8 C9 . . . . -42.10(17) ?
C7 C8 C9 C10 . . . . -40.53(16) ?
C8 C9 C10 C11 . . . . 70.15(17) ?
C9 C10 C11 C1 . . . . -1.15(19) ?
C9 C10 C11 C12 . . . . 175.85(11) ?
C2 C1 C11 C10 . . . . 132.20(13) ?
C6 C1 C11 C10 . . . . -45.78(17) ?
C2 C1 C11 C12 . . . . -45.00(15) ?
C6 C1 C11 C12 . . . . 137.02(12) ?
C10 C11 C12 C13 . . . . -74.21(17) ?
C1 C11 C12 C13 . . . . 102.92(13) ?
C10 C11 C12 C17 . . . . 109.20(14) ?
C1 C11 C12 C17 . . . . -73.67(14) ?
C17 C12 C13 C14 . . . . 2.74(18) ?
C11 C12 C13 C14 . . . . -173.91(11) ?
C12 C13 C14 C15 . . . . 0.63(19) ?
C13 C14 C15 C16 . . . . -3.30(18) ?
C13 C14 C15 C19 . . . . 173.77(11) ?
C14 C15 C16 C17 . . . . 2.57(18) ?
C19 C15 C16 C17 . . . . -174.45(11) ?
C18 O1 C17 C16 . . . . 3.63(18) ?
C18 O1 C17 C12 . . . . -176.42(11) ?
C15 C16 C17 O1 . . . . -179.22(11) ?
C15 C16 C17 C12 . . . . 0.84(18) ?
C13 C12 C17 O1 . . . . 176.58(10) ?
C11 C12 C17 O1 . . . . -6.69(16) ?
C13 C12 C17 C16 . . . . -3.47(17) ?
C11 C12 C17 C16 . . . . 173.26(11) ?
C14 C15 C19 C20 . . . . -167.16(13) ?
C16 C15 C19 C20 . . . . 9.8(2) ?
C15 C19 C20 C21 . . . . 177.51(12) ?
C22 O3 C21 O2 . . . . -0.71(18) ?
C22 O3 C21 C20 . . . . 178.41(11) ?
C19 C20 C21 O2 . . . . -2.8(2) ?
C19 C20 C21 O3 . . . . 178.10(12) ?
C21 O3 C22 C23 . . . . -176.91(13) ?



