# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_X
_audit_block_doi                 10.5517/ccdc.csd.cc2h6zzp
_database_code_depnum_ccdc_archive 'CCDC 2300633'
loop_
_audit_author_name
_audit_author_address
'Yishu Bao'
;the Chinese University of Hong Kong
China
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 O'
_chemical_formula_weight         268.30

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   12.929(3)
_cell_length_b                   3.9490(8)
_cell_length_c                   13.092(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.70(3)
_cell_angle_gamma                90
_cell_volume                     649.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1388
_diffrn_reflns_av_unetI/netI     0.1749
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.601
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.578
_diffrn_reflns_point_group_measured_fraction_full 0.579
_reflns_number_total             1388
_reflns_number_gt                556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0100P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1388
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_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
O O 0.6426(4) 0.4237(16) 0.0312(4) 0.0608(17) Uani 1 1 d . . . . .
C1 C 0.7426(6) 0.579(2) 0.0732(6) 0.055(3) Uani 1 1 d . . . . .
C2 C 0.7877(6) 0.576(2) 0.1822(6) 0.050(2) Uani 1 1 d . . . . .
C3 C 0.7387(6) 0.440(2) 0.2591(6) 0.063(3) Uani 1 1 d . . . . .
H3A H 0.6733 0.3312 0.2385 0.076 Uiso 1 1 calc R U . . .
C4 C 0.7873(7) 0.468(3) 0.3636(7) 0.089(4) Uani 1 1 d . . . . .
H4A H 0.7549 0.3826 0.4144 0.107 Uiso 1 1 calc R U . . .
C5 C 0.8876(7) 0.628(3) 0.3929(7) 0.088(4) Uani 1 1 d . . . . .
H5A H 0.9216 0.6457 0.4637 0.106 Uiso 1 1 calc R U . . .
C6 C 0.9363(6) 0.759(2) 0.3175(7) 0.071(3) Uani 1 1 d . . . . .
H6A H 1.0025 0.8624 0.3387 0.085 Uiso 1 1 calc R U . . .
C7 C 0.8875(7) 0.737(2) 0.2099(7) 0.066(3) Uani 1 1 d . . . . .
C8 C 0.9371(6) 0.872(3) 0.1320(6) 0.069(3) Uani 1 1 d . . . . .
H8A H 1.0043 0.9698 0.1524 0.083 Uiso 1 1 calc R U . . .
C9 C 0.8866(5) 0.858(2) 0.0279(6) 0.053(2) Uani 1 1 d . . . . .
H9A H 0.9178 0.9536 -0.0224 0.063 Uiso 1 1 calc R U . . .
C10 C 0.7866(5) 0.697(2) -0.0025(6) 0.053(3) Uani 1 1 d . . . . .
C11 C 0.7118(6) 0.633(2) -0.0999(6) 0.052(2) Uani 1 1 d . . . . .
C12 C 0.7054(6) 0.700(2) -0.2077(6) 0.047(2) Uani 1 1 d . . . . .
C13 C 0.7835(6) 0.863(2) -0.2472(6) 0.066(3) Uani 1 1 d . . . . .
H13A H 0.8453 0.9368 -0.2005 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7719(6) 0.918(2) -0.3530(6) 0.071(3) Uani 1 1 d . . . . .
H14A H 0.8245 1.0305 -0.3773 0.085 Uiso 1 1 calc R U . . .
C15 C 0.6807(6) 0.803(2) -0.4232(6) 0.068(3) Uani 1 1 d . . . . .
H15A H 0.6743 0.8310 -0.4950 0.082 Uiso 1 1 calc R U . . .
C16 C 0.6015(5) 0.652(2) -0.3899(6) 0.064(3) Uani 1 1 d . . . . .
H16A H 0.5399 0.5871 -0.4385 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6109(6) 0.591(2) -0.2806(6) 0.059(3) Uani 1 1 d . . . . .
C18 C 0.5280(6) 0.426(3) -0.2466(6) 0.070(3) Uani 1 1 d . . . . .
H18A H 0.4671 0.3582 -0.2957 0.084 Uiso 1 1 calc R U . . .
C19 C 0.5363(5) 0.367(2) -0.1448(5) 0.059(3) Uani 1 1 d . . . . .
H19A H 0.4828 0.2565 -0.1212 0.071 Uiso 1 1 calc R U . . .
C20 C 0.6264(5) 0.477(2) -0.0769(6) 0.049(2) 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
O C20 1.397(7) . ?
O C1 1.417(8) . ?
C1 C10 1.338(9) . ?
C1 C2 1.409(9) . ?
C2 C7 1.406(9) . ?
C2 C3 1.417(9) . ?
C3 C4 1.367(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.411(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.391(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.403(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.430(10) . ?
C8 C9 1.366(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.409(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.430(9) . ?
C11 C20 1.358(9) . ?
C11 C12 1.419(9) . ?
C12 C13 1.396(9) . ?
C12 C17 1.427(8) . ?
C13 C14 1.375(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.388(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.343(9) . ?
C15 H15A 0.9300 . ?
C16 C17 1.427(9) . ?
C16 H16A 0.9300 . ?
C17 C18 1.414(10) . ?
C18 C19 1.332(8) . ?
C18 H18A 0.9300 . ?
C19 C20 1.358(8) . ?
C19 H19A 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
C20 O C1 103.4(6) . . ?
C10 C1 C2 127.2(8) . . ?
C10 C1 O 111.9(7) . . ?
C2 C1 O 120.7(8) . . ?
C7 C2 C1 113.1(8) . . ?
C7 C2 C3 121.7(8) . . ?
C1 C2 C3 125.1(8) . . ?
C4 C3 C2 120.2(9) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 118.9(10) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 120.9(9) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C7 121.2(9) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C6 C7 C2 117.0(9) . . ?
C6 C7 C8 121.4(10) . . ?
C2 C7 C8 121.6(8) . . ?
C9 C8 C7 120.5(8) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 119.3(8) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C1 C10 C9 118.1(8) . . ?
C1 C10 C11 106.3(7) . . ?
C9 C10 C11 135.5(8) . . ?
C20 C11 C12 116.5(7) . . ?
C20 C11 C10 107.2(7) . . ?
C12 C11 C10 136.2(8) . . ?
C13 C12 C11 125.3(8) . . ?
C13 C12 C17 118.1(7) . . ?
C11 C12 C17 116.6(7) . . ?
C14 C13 C12 121.9(8) . . ?
C14 C13 H13A 119.0 . . ?
C12 C13 H13A 119.0 . . ?
C13 C14 C15 119.3(8) . . ?
C13 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
C16 C15 C14 121.5(8) . . ?
C16 C15 H15A 119.2 . . ?
C14 C15 H15A 119.2 . . ?
C15 C16 C17 120.7(8) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C18 C17 C16 120.2(8) . . ?
C18 C17 C12 121.4(7) . . ?
C16 C17 C12 118.4(7) . . ?
C19 C18 C17 120.6(8) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 116.9(8) . . ?
C18 C19 H19A 121.6 . . ?
C20 C19 H19A 121.6 . . ?
C11 C20 C19 128.0(8) . . ?
C11 C20 O 111.0(6) . . ?
C19 C20 O 120.9(8) . . ?

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
C20 O C1 C10 -3.5(9) . . . . ?
C20 O C1 C2 -179.6(7) . . . . ?
C10 C1 C2 C7 3.8(12) . . . . ?
O C1 C2 C7 179.2(8) . . . . ?
C10 C1 C2 C3 -178.4(9) . . . . ?
O C1 C2 C3 -3.0(12) . . . . ?
C7 C2 C3 C4 1.2(13) . . . . ?
C1 C2 C3 C4 -176.4(9) . . . . ?
C2 C3 C4 C5 -1.3(15) . . . . ?
C3 C4 C5 C6 0.6(15) . . . . ?
C4 C5 C6 C7 0.1(15) . . . . ?
C5 C6 C7 C2 -0.2(14) . . . . ?
C5 C6 C7 C8 179.8(9) . . . . ?
C1 C2 C7 C6 177.4(8) . . . . ?
C3 C2 C7 C6 -0.4(13) . . . . ?
C1 C2 C7 C8 -2.6(12) . . . . ?
C3 C2 C7 C8 179.5(9) . . . . ?
C6 C7 C8 C9 -177.8(9) . . . . ?
C2 C7 C8 C9 2.3(14) . . . . ?
C7 C8 C9 C10 -2.4(14) . . . . ?
C2 C1 C10 C9 -4.2(13) . . . . ?
O C1 C10 C9 -179.9(8) . . . . ?
C2 C1 C10 C11 178.0(8) . . . . ?
O C1 C10 C11 2.3(10) . . . . ?
C8 C9 C10 C1 3.2(13) . . . . ?
C8 C9 C10 C11 -179.8(10) . . . . ?
C1 C10 C11 C20 -0.1(10) . . . . ?
C9 C10 C11 C20 -177.3(10) . . . . ?
C1 C10 C11 C12 177.5(10) . . . . ?
C9 C10 C11 C12 0.3(19) . . . . ?
C20 C11 C12 C13 178.7(9) . . . . ?
C10 C11 C12 C13 1.2(16) . . . . ?
C20 C11 C12 C17 -1.1(11) . . . . ?
C10 C11 C12 C17 -178.6(10) . . . . ?
C11 C12 C13 C14 179.7(9) . . . . ?
C17 C12 C13 C14 -0.5(12) . . . . ?
C12 C13 C14 C15 -1.1(14) . . . . ?
C13 C14 C15 C16 2.9(15) . . . . ?
C14 C15 C16 C17 -2.9(14) . . . . ?
C15 C16 C17 C18 -178.7(9) . . . . ?
C15 C16 C17 C12 1.2(13) . . . . ?
C13 C12 C17 C18 -179.6(9) . . . . ?
C11 C12 C17 C18 0.2(12) . . . . ?
C13 C12 C17 C16 0.4(11) . . . . ?
C11 C12 C17 C16 -179.7(8) . . . . ?
C16 C17 C18 C19 179.8(9) . . . . ?
C12 C17 C18 C19 -0.1(14) . . . . ?
C17 C18 C19 C20 0.9(14) . . . . ?
C12 C11 C20 C19 2.1(14) . . . . ?
C10 C11 C20 C19 -179.7(9) . . . . ?
C12 C11 C20 O 179.6(8) . . . . ?
C10 C11 C20 O -2.2(10) . . . . ?
C18 C19 C20 C11 -2.0(14) . . . . ?
C18 C19 C20 O -179.3(9) . . . . ?
C1 O C20 C11 3.4(9) . . . . ?
C1 O C20 C19 -178.8(8) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.040

