# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2019Mar_sampleC
_database_code_depnum_ccdc_archive 'CCDC 2312076'
loop_
_audit_author_name
_audit_author_address
'Kiyoshi Tsuge'
;Graduate School of Science and Engineering, University of Toyama
Japan
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-03-08 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      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.08906(16)
_cell_length_b                   9.90544(18)
_cell_length_c                   20.1477(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.251(7)
_cell_angle_gamma                90.0000
_cell_volume                     1812.52(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16450
_cell_measurement_theta_min      4.39
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768.00
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.904

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            20217
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_theta_max         68.174
_diffrn_reflns_theta_min         4.392
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3298
_reflns_number_gt                3096
_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          0.0358
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0813
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     246
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0360P)²+0.5553P] 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          0.001
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.24
_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 0.0181 0.0091
;
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 0.0492 0.0322
;
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 0.20580(9) 0.27451(8) 0.64986(4) 0.0297(2) Uani 1 1 d . . . . .
O2 O 0.22265(8) 0.51077(8) 0.66420(4) 0.02786(19) Uani 1 1 d . . . . .
O3 O 0.37346(9) 0.13628(8) 0.69139(5) 0.0343(2) Uani 1 1 d . . . . .
O5 O 0.71157(9) 0.15480(9) 0.72492(4) 0.0328(2) Uani 1 1 d . . . . .
O4 O 0.42055(9) 0.60170(8) 0.71100(5) 0.0350(2) Uani 1 1 d . . . . .
C1 C 0.39050(12) 0.36482(11) 0.72971(6) 0.0241(2) Uani 1 1 d . . . . .
C2 C 0.55933(12) 0.34318(12) 0.74678(5) 0.0241(2) Uani 1 1 d . . . . .
H2 H 0.609059 0.432619 0.752882 0.029 Uiso 1 1 calc R U . . .
C3 C 0.52218(12) 0.28467(12) 0.81480(6) 0.0263(3) Uani 1 1 d . . . . .
H3 H 0.511135 0.184595 0.810380 0.032 Uiso 1 1 calc R U . . .
C4 C 0.36808(12) 0.35005(13) 0.80707(6) 0.0277(3) Uani 1 1 d . . . . .
H4A H 0.359877 0.437403 0.830518 0.033 Uiso 1 1 calc R U . . .
H4B H 0.286599 0.288693 0.818098 0.033 Uiso 1 1 calc R U . . .
C5 C 0.32365(12) 0.24819(12) 0.69031(6) 0.0251(2) Uani 1 1 d . . . . .
C6 C 0.12302(13) 0.39735(12) 0.65724(6) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.34800(12) 0.50180(12) 0.70206(6) 0.0253(2) Uani 1 1 d . . . . .
C8 C 0.03963(14) 0.41888(14) 0.59200(6) 0.0358(3) Uani 1 1 d . . . . .
H8A H 0.108872 0.420220 0.555922 0.043 Uiso 1 1 calc R U . . .
H8B H -0.013051 0.505121 0.593084 0.043 Uiso 1 1 calc R U . . .
H8C H -0.031171 0.345290 0.584536 0.043 Uiso 1 1 calc R U . . .
C9 C 0.02594(13) 0.38598(13) 0.71593(6) 0.0312(3) Uani 1 1 d . . . . .
H9A H 0.087326 0.382428 0.756979 0.037 Uiso 1 1 calc R U . . .
H9B H -0.033292 0.303506 0.711861 0.037 Uiso 1 1 calc R U . . .
H9C H -0.039354 0.464604 0.717104 0.037 Uiso 1 1 calc R U . . .
C10 C 0.64864(12) 0.25411(12) 0.70221(6) 0.0257(2) Uani 1 1 d . . . . .
C11 C 0.66034(12) 0.29244(12) 0.63100(6) 0.0270(3) Uani 1 1 d . . . . .
C12 C 0.64362(13) 0.42527(13) 0.60917(6) 0.0314(3) Uani 1 1 d . . . . .
H12 H 0.621367 0.494597 0.639776 0.038 Uiso 1 1 calc R U . . .
C13 C 0.65954(14) 0.45609(14) 0.54258(7) 0.0369(3) Uani 1 1 d . . . . .
H13 H 0.650626 0.546938 0.527853 0.044 Uiso 1 1 calc R U . . .
C14 C 0.68835(14) 0.35477(15) 0.49769(6) 0.0374(3) Uani 1 1 d . . . . .
H14 H 0.697221 0.375820 0.452019 0.045 Uiso 1 1 calc R U . . .
C15 C 0.70429(14) 0.22266(14) 0.51927(6) 0.0355(3) Uani 1 1 d . . . . .
H15 H 0.723587 0.153271 0.488243 0.043 Uiso 1 1 calc R U . . .
C16 C 0.69229(13) 0.19112(13) 0.58568(6) 0.0310(3) Uani 1 1 d . . . . .
H16 H 0.705760 0.100698 0.600415 0.037 Uiso 1 1 calc R U . . .
C17 C 0.62208(13) 0.31425(12) 0.87446(6) 0.0284(3) Uani 1 1 d . . . . .
C18 C 0.77401(14) 0.30682(14) 0.86982(7) 0.0366(3) Uani 1 1 d . . . . .
H18 H 0.814951 0.287539 0.828207 0.044 Uiso 1 1 calc R U . . .
C19 C 0.86637(16) 0.32724(16) 0.92523(8) 0.0459(4) Uani 1 1 d . . . . .
H19 H 0.970035 0.322635 0.921176 0.055 Uiso 1 1 calc R U . . .
C20 C 0.80921(18) 0.35419(15) 0.98626(7) 0.0457(4) Uani 1 1 d . . . . .
H20 H 0.872836 0.367091 1.024276 0.055 Uiso 1 1 calc R U . . .
C21 C 0.65897(19) 0.36217(15) 0.99143(7) 0.0459(4) Uani 1 1 d . . . . .
H21 H 0.618588 0.380850 1.033231 0.055 Uiso 1 1 calc R U . . .
C22 C 0.56606(16) 0.34306(14) 0.93586(7) 0.0389(3) Uani 1 1 d . . . . .
H22 H 0.462562 0.349846 0.939987 0.047 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    'SHELXT Version 2018/2 (Sheldrick, 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 C5 1.3457(14) . ?
O1 C6 1.4414(14) . ?
O2 C7 1.3489(14) . ?
O2 C6 1.4464(14) . ?
O3 C5 1.1973(14) . ?
O5 C10 1.2181(14) . ?
O4 C7 1.1988(14) . ?
C1 C7 1.5111(16) . ?
C1 C5 1.5153(16) . ?
C1 C2 1.5740(15) . ?
C1 C4 1.5866(15) . ?
C2 C10 1.5168(16) . ?
C2 C3 1.5377(15) . ?
C2 H2 1.0000 . ?
C3 C17 1.5065(16) . ?
C3 C4 1.5454(16) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C8 1.5066(16) . ?
C6 C9 1.5071(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4921(16) . ?
C11 C12 1.3937(17) . ?
C11 C16 1.3950(17) . ?
C12 C13 1.3890(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3826(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3858(18) . ?
C17 C18 1.3897(18) . ?
C18 C19 1.3850(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C5 O1 C6 120.49(9) . . ?
C7 O2 C6 121.02(9) . . ?
C7 C1 C5 113.58(9) . . ?
C7 C1 C2 115.83(9) . . ?
C5 C1 C2 112.21(9) . . ?
C7 C1 C4 113.84(9) . . ?
C5 C1 C4 112.34(9) . . ?
C2 C1 C4 86.25(8) . . ?
C10 C2 C3 116.73(10) . . ?
C10 C2 C1 119.32(9) . . ?
C3 C2 C1 89.98(8) . . ?
C10 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C17 C3 C2 119.43(10) . . ?
C17 C3 C4 120.95(10) . . ?
C2 C3 C4 88.98(8) . . ?
C17 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C3 C4 C1 89.24(8) . . ?
C3 C4 H4A 113.8 . . ?
C1 C4 H4A 113.8 . . ?
C3 C4 H4B 113.8 . . ?
C1 C4 H4B 113.8 . . ?
H4A C4 H4B 111.0 . . ?
O3 C5 O1 118.80(10) . . ?
O3 C5 C1 123.56(10) . . ?
O1 C5 C1 117.57(10) . . ?
O1 C6 O2 109.77(9) . . ?
O1 C6 C8 106.03(10) . . ?
O2 C6 C8 105.44(10) . . ?
O1 C6 C9 110.00(10) . . ?
O2 C6 C9 111.45(10) . . ?
C8 C6 C9 113.90(10) . . ?
O4 C7 O2 118.55(10) . . ?
O4 C7 C1 123.69(10) . . ?
O2 C7 C1 117.75(10) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 C11 121.10(10) . . ?
O5 C10 C2 120.12(10) . . ?
C11 C10 C2 118.77(10) . . ?
C12 C11 C16 119.71(11) . . ?
C12 C11 C10 122.18(11) . . ?
C16 C11 C10 118.09(11) . . ?
C13 C12 C11 119.87(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.12(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.04(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.41(12) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 119.82(12) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C22 C17 C18 118.15(12) . . ?
C22 C17 C3 121.42(11) . . ?
C18 C17 C3 120.36(11) . . ?
C19 C18 C17 120.70(13) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.60(14) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 119.22(13) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.34(14) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.98(13) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?

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
_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 C1 C2 C10 -106.71(12) . . . . ?
C5 C1 C2 C10 25.95(14) . . . . ?
C4 C1 C2 C10 138.57(10) . . . . ?
C7 C1 C2 C3 132.25(10) . . . . ?
C5 C1 C2 C3 -95.09(10) . . . . ?
C4 C1 C2 C3 17.53(8) . . . . ?
C10 C2 C3 C17 93.29(13) . . . . ?
C1 C2 C3 C17 -143.46(10) . . . . ?
C10 C2 C3 C4 -141.22(10) . . . . ?
C1 C2 C3 C4 -17.98(8) . . . . ?
C17 C3 C4 C1 142.04(11) . . . . ?
C2 C3 C4 C1 17.83(8) . . . . ?
C7 C1 C4 C3 -134.08(10) . . . . ?
C5 C1 C4 C3 95.05(10) . . . . ?
C2 C1 C4 C3 -17.44(8) . . . . ?
C6 O1 C5 O3 166.35(10) . . . . ?
C6 O1 C5 C1 -16.54(15) . . . . ?
C7 C1 C5 O3 157.95(11) . . . . ?
C2 C1 C5 O3 24.19(16) . . . . ?
C4 C1 C5 O3 -71.05(14) . . . . ?
C7 C1 C5 O1 -19.01(14) . . . . ?
C2 C1 C5 O1 -152.77(9) . . . . ?
C4 C1 C5 O1 111.99(11) . . . . ?
C5 O1 C6 O2 46.30(13) . . . . ?
C5 O1 C6 C8 159.73(10) . . . . ?
C5 O1 C6 C9 -76.68(12) . . . . ?
C7 O2 C6 O1 -41.47(13) . . . . ?
C7 O2 C6 C8 -155.28(10) . . . . ?
C7 O2 C6 C9 80.65(12) . . . . ?
C6 O2 C7 O4 -173.57(10) . . . . ?
C6 O2 C7 C1 7.67(15) . . . . ?
C5 C1 C7 O4 -155.34(11) . . . . ?
C2 C1 C7 O4 -23.31(16) . . . . ?
C4 C1 C7 O4 74.41(14) . . . . ?
C5 C1 C7 O2 23.36(14) . . . . ?
C2 C1 C7 O2 155.38(9) . . . . ?
C4 C1 C7 O2 -106.89(11) . . . . ?
C3 C2 C10 O5 -14.35(15) . . . . ?
C1 C2 C10 O5 -120.76(12) . . . . ?
C3 C2 C10 C11 167.05(10) . . . . ?
C1 C2 C10 C11 60.64(14) . . . . ?
O5 C10 C11 C12 -153.69(11) . . . . ?
C2 C10 C11 C12 24.89(16) . . . . ?
O5 C10 C11 C16 24.90(16) . . . . ?
C2 C10 C11 C16 -156.52(10) . . . . ?
C16 C11 C12 C13 -0.32(17) . . . . ?
C10 C11 C12 C13 178.25(11) . . . . ?
C11 C12 C13 C14 1.59(18) . . . . ?
C12 C13 C14 C15 -1.28(19) . . . . ?
C13 C14 C15 C16 -0.31(19) . . . . ?
C14 C15 C16 C11 1.58(18) . . . . ?
C12 C11 C16 C15 -1.26(17) . . . . ?
C10 C11 C16 C15 -179.89(10) . . . . ?
C2 C3 C17 C22 139.25(12) . . . . ?
C4 C3 C17 C22 30.93(17) . . . . ?
C2 C3 C17 C18 -43.87(16) . . . . ?
C4 C3 C17 C18 -152.19(12) . . . . ?
C22 C17 C18 C19 0.2(2) . . . . ?
C3 C17 C18 C19 -176.75(12) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C18 C19 C20 C21 -0.7(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C18 C17 C22 C21 -0.9(2) . . . . ?
C3 C17 C22 C21 176.08(12) . . . . ?
C20 C21 C22 C17 0.7(2) . . . . ?


#==============================================================================
# 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
#==============================================================================
