# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_TD83_5_5Ac
_database_code_depnum_ccdc_archive 'CCDC 2141535'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Yoshimura'
;Kanazawa University
Japan
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H20 O5'
_chemical_formula_moiety         'C22 H20 O5'
_chemical_formula_weight         364.40
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.0739(11)
_cell_length_b                   10.3439(14)
_cell_length_c                   11.7531(15)
_cell_angle_alpha                86.740(6)
_cell_angle_beta                 88.944(6)
_cell_angle_gamma                73.863(5)
_cell_volume                     941.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2400
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      27.04
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384.00
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.191
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            9273
_diffrn_reflns_av_unetI/netI     0.2273
_diffrn_reflns_av_R_equivalents  0.1753
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         1.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4291
_reflns_number_gt                1408
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2630
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.3431
_refine_ls_wR_factor_gt          0.2296
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4291
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1659P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.3112(4) 0.3333(4) 0.2090(3) 0.0508(10) Uani 1 1 d . . . . .
O2 O 0.2699(5) 0.5367(4) 0.4405(3) 0.0650(12) Uani 1 1 d . . . . .
O3 O 0.0865(5) 0.3407(4) 0.3394(3) 0.0540(11) Uani 1 1 d . . . . .
O4 O 0.2928(5) 0.2353(4) 0.4620(3) 0.0650(12) Uani 1 1 d . . . . .
O5 O 0.6679(6) 0.0975(4) 0.3444(4) 0.0825(14) Uani 1 1 d . . . . .
C1 C 0.4877(6) 0.2881(6) 0.2483(4) 0.0462(13) Uani 1 1 d . . . . .
C2 C 0.6038(8) 0.3203(6) 0.1509(5) 0.0666(18) Uani 1 1 d . . . . .
H2A H 0.720736 0.262394 0.159032 0.080 Uiso 1 1 calc R U . . .
H2B H 0.559650 0.307921 0.077353 0.080 Uiso 1 1 calc R U . . .
C3 C 0.5990(9) 0.4657(7) 0.1624(5) 0.078(2) Uani 1 1 d . . . . .
H3A H 0.493211 0.525804 0.131224 0.094 Uiso 1 1 calc R U . . .
H3B H 0.696603 0.486632 0.124100 0.094 Uiso 1 1 calc R U . . .
C4 C 0.6079(8) 0.4763(6) 0.2901(5) 0.0611(17) Uani 1 1 d . . . . .
H4A H 0.557109 0.568361 0.310985 0.073 Uiso 1 1 calc R U . . .
H4B H 0.726447 0.446952 0.316199 0.073 Uiso 1 1 calc R U . . .
C5 C 0.5038(7) 0.3824(6) 0.3418(4) 0.0499(14) Uani 1 1 d . . . . .
H5 H 0.563058 0.330062 0.408597 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3198(7) 0.4533(5) 0.3706(4) 0.0463(13) Uani 1 1 d . . . . .
C7 C 0.1994(7) 0.4156(5) 0.2849(4) 0.0437(13) Uani 1 1 d . . . . .
C8 C 0.0793(7) 0.5358(6) 0.2271(4) 0.0465(13) Uani 1 1 d . . . . .
C9 C -0.0518(7) 0.6205(6) 0.2903(5) 0.0555(15) Uani 1 1 d . . . . .
H9 H -0.064893 0.598425 0.367108 0.067 Uiso 1 1 calc R U . . .
C10 C -0.1605(8) 0.7349(7) 0.2412(6) 0.0714(18) Uani 1 1 d . . . . .
H10 H -0.243730 0.791493 0.285219 0.086 Uiso 1 1 calc R U . . .
C11 C -0.1469(9) 0.7669(7) 0.1254(7) 0.0726(19) Uani 1 1 d . . . . .
H11 H -0.223273 0.843239 0.091575 0.087 Uiso 1 1 calc R U . . .
C12 C -0.0217(10) 0.6863(7) 0.0616(6) 0.0739(19) Uani 1 1 d . . . . .
H12 H -0.012004 0.708265 -0.015596 0.089 Uiso 1 1 calc R U . . .
C13 C 0.0921(8) 0.5711(6) 0.1116(5) 0.0579(16) Uani 1 1 d . . . . .
H13 H 0.177617 0.517014 0.067395 0.069 Uiso 1 1 calc R U . . .
C14 C 0.1531(8) 0.2496(6) 0.4246(5) 0.0501(14) Uani 1 1 d . . . . .
C15 C 0.0317(8) 0.1673(7) 0.4638(5) 0.0703(18) Uani 1 1 d . . . . .
H15A H -0.073471 0.197449 0.421027 0.084 Uiso 1 1 calc R U . . .
H15B H 0.084990 0.073867 0.451865 0.084 Uiso 1 1 calc R U . . .
H15C H 0.006678 0.178605 0.543398 0.084 Uiso 1 1 calc R U . . .
C16 C 0.5398(8) 0.1400(6) 0.2880(5) 0.0565(15) Uani 1 1 d . . . . .
C17 C 0.4371(7) 0.0464(6) 0.2590(5) 0.0519(14) Uani 1 1 d . . . . .
C18 C 0.4271(8) -0.0554(6) 0.3376(5) 0.0599(16) Uani 1 1 d . . . . .
H18 H 0.483638 -0.064146 0.407082 0.072 Uiso 1 1 calc R U . . .
C19 C 0.3346(9) -0.1438(7) 0.3144(6) 0.079(2) Uani 1 1 d . . . . .
H19 H 0.325470 -0.210117 0.369113 0.095 Uiso 1 1 calc R U . . .
C20 C 0.2573(11) -0.1348(8) 0.2129(8) 0.104(3) Uani 1 1 d . . . . .
H20 H 0.194633 -0.195034 0.198231 0.125 Uiso 1 1 calc R U . . .
C21 C 0.2693(12) -0.0375(8) 0.1297(8) 0.113(3) Uani 1 1 d . . . . .
H21 H 0.218982 -0.034254 0.058679 0.136 Uiso 1 1 calc R U . . .
C22 C 0.3567(10) 0.0541(7) 0.1537(6) 0.084(2) Uani 1 1 d . . . . .
H22 H 0.362402 0.121708 0.099415 0.101 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C7 1.402(6) . ?
O1 C1 1.446(6) . ?
O2 C6 1.207(6) . ?
O3 C14 1.345(6) . ?
O3 C7 1.469(6) . ?
O4 C14 1.185(6) . ?
O5 C16 1.201(7) . ?
C1 C16 1.520(8) . ?
C1 C5 1.540(7) . ?
C1 C2 1.546(7) . ?
C2 C3 1.507(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.516(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.545(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.505(7) . ?
C5 H5 0.9800 . ?
C6 C7 1.551(7) . ?
C7 C8 1.485(8) . ?
C8 C13 1.395(7) . ?
C8 C9 1.403(7) . ?
C9 C10 1.366(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.361(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.517(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.495(8) . ?
C17 C18 1.379(7) . ?
C17 C22 1.396(8) . ?
C18 C19 1.373(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.343(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(9) . ?
C21 H21 0.9300 . ?
C22 H22 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
C7 O1 C1 113.3(4) . . ?
C14 O3 C7 117.6(4) . . ?
O1 C1 C16 112.3(4) . . ?
O1 C1 C5 106.5(4) . . ?
C16 C1 C5 113.4(4) . . ?
O1 C1 C2 107.7(4) . . ?
C16 C1 C2 112.6(5) . . ?
C5 C1 C2 103.9(4) . . ?
C3 C2 C1 105.1(4) . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C2 C3 C4 103.2(5) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 C5 104.8(5) . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C1 103.8(4) . . ?
C6 C5 C4 114.3(5) . . ?
C1 C5 C4 107.0(4) . . ?
C6 C5 H5 110.5 . . ?
C1 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
O2 C6 C5 127.2(5) . . ?
O2 C6 C7 123.6(5) . . ?
C5 C6 C7 108.8(4) . . ?
O1 C7 O3 109.3(4) . . ?
O1 C7 C8 113.0(4) . . ?
O3 C7 C8 104.5(4) . . ?
O1 C7 C6 104.7(4) . . ?
O3 C7 C6 112.9(4) . . ?
C8 C7 C6 112.6(4) . . ?
C13 C8 C9 117.5(6) . . ?
C13 C8 C7 122.9(5) . . ?
C9 C8 C7 119.5(5) . . ?
C10 C9 C8 121.3(6) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.1(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.0(7) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.8(6) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
O4 C14 O3 122.7(5) . . ?
O4 C14 C15 124.8(6) . . ?
O3 C14 C15 112.5(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C17 119.3(6) . . ?
O5 C16 C1 118.5(5) . . ?
C17 C16 C1 122.2(5) . . ?
C18 C17 C22 118.5(6) . . ?
C18 C17 C16 118.7(5) . . ?
C22 C17 C16 122.7(5) . . ?
C19 C18 C17 120.7(6) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.1(7) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.2(8) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 119.0(7) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C17 120.5(7) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?

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
C7 O1 C1 C16 106.7(5) . . . . ?
C7 O1 C1 C5 -17.9(5) . . . . ?
C7 O1 C1 C2 -128.8(4) . . . . ?
O1 C1 C2 C3 83.5(6) . . . . ?
C16 C1 C2 C3 -152.3(5) . . . . ?
C5 C1 C2 C3 -29.3(6) . . . . ?
C1 C2 C3 C4 40.6(7) . . . . ?
C2 C3 C4 C5 -35.7(6) . . . . ?
O1 C1 C5 C6 14.6(5) . . . . ?
C16 C1 C5 C6 -109.4(5) . . . . ?
C2 C1 C5 C6 128.1(5) . . . . ?
O1 C1 C5 C4 -106.6(5) . . . . ?
C16 C1 C5 C4 129.4(5) . . . . ?
C2 C1 C5 C4 6.9(6) . . . . ?
C3 C4 C5 C6 -96.8(6) . . . . ?
C3 C4 C5 C1 17.6(6) . . . . ?
C1 C5 C6 O2 179.6(5) . . . . ?
C4 C5 C6 O2 -64.2(7) . . . . ?
C1 C5 C6 C7 -7.3(5) . . . . ?
C4 C5 C6 C7 108.8(5) . . . . ?
C1 O1 C7 O3 -108.4(4) . . . . ?
C1 O1 C7 C8 135.8(4) . . . . ?
C1 O1 C7 C6 12.9(5) . . . . ?
C14 O3 C7 O1 78.0(5) . . . . ?
C14 O3 C7 C8 -160.8(4) . . . . ?
C14 O3 C7 C6 -38.1(6) . . . . ?
O2 C6 C7 O1 170.7(5) . . . . ?
C5 C6 C7 O1 -2.7(5) . . . . ?
O2 C6 C7 O3 -70.5(7) . . . . ?
C5 C6 C7 O3 116.1(5) . . . . ?
O2 C6 C7 C8 47.5(7) . . . . ?
C5 C6 C7 C8 -125.8(5) . . . . ?
O1 C7 C8 C13 -7.6(7) . . . . ?
O3 C7 C8 C13 -126.3(5) . . . . ?
C6 C7 C8 C13 110.8(5) . . . . ?
O1 C7 C8 C9 173.7(4) . . . . ?
O3 C7 C8 C9 55.0(6) . . . . ?
C6 C7 C8 C9 -67.9(6) . . . . ?
C13 C8 C9 C10 -1.4(8) . . . . ?
C7 C8 C9 C10 177.4(5) . . . . ?
C8 C9 C10 C11 2.4(9) . . . . ?
C9 C10 C11 C12 -2.0(9) . . . . ?
C10 C11 C12 C13 0.6(10) . . . . ?
C11 C12 C13 C8 0.4(9) . . . . ?
C9 C8 C13 C12 0.0(8) . . . . ?
C7 C8 C13 C12 -178.8(5) . . . . ?
C7 O3 C14 O4 5.7(7) . . . . ?
C7 O3 C14 C15 -173.0(4) . . . . ?
O1 C1 C16 O5 -164.4(5) . . . . ?
C5 C1 C16 O5 -43.6(7) . . . . ?
C2 C1 C16 O5 73.9(7) . . . . ?
O1 C1 C16 C17 15.7(7) . . . . ?
C5 C1 C16 C17 136.5(5) . . . . ?
C2 C1 C16 C17 -106.0(6) . . . . ?
O5 C16 C17 C18 34.5(8) . . . . ?
C1 C16 C17 C18 -145.6(5) . . . . ?
O5 C16 C17 C22 -142.7(7) . . . . ?
C1 C16 C17 C22 37.2(8) . . . . ?
C22 C17 C18 C19 -2.5(9) . . . . ?
C16 C17 C18 C19 -179.8(5) . . . . ?
C17 C18 C19 C20 2.2(10) . . . . ?
C18 C19 C20 C21 0.3(13) . . . . ?
C19 C20 C21 C22 -2.4(14) . . . . ?
C20 C21 C22 C17 2.1(13) . . . . ?
C18 C17 C22 C21 0.3(10) . . . . ?
C16 C17 C22 C21 177.5(7) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5a'
