# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_cl-1_autored
_database_code_depnum_ccdc_archive 'CCDC 2184325'
loop_
_audit_author_name
_audit_author_address
bbbbb
;FJIRSM
China
;
_audit_update_record             
;
2022-07-06 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 O7'
_chemical_formula_sum            'C21 H24 O7'
_chemical_formula_weight         388.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.1896(3)
_cell_length_b                   5.80260(10)
_cell_length_c                   20.7903(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.598(2)
_cell_angle_gamma                90
_cell_volume                     1941.15(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23888
_cell_measurement_theta_min      2.4630
_cell_measurement_theta_max      60.4060

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.529
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.3405
_diffrn_radiation_type           GaK\a
_diffrn_source                   'micro-focus metaljet'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            38963
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.506
_diffrn_reflns_theta_max         60.510
_diffrn_reflns_theta_full        53.543
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4411
_reflns_number_gt                3760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0545P)²+0.4410P] 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_number_reflns         4411
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_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
O18 O 0.37219(5) 0.24428(14) 0.59140(4) 0.0188(2) Uani 1 1 d . . . . .
O28 O 0.28451(5) 0.74482(14) 0.74535(5) 0.0205(2) Uani 1 1 d . . . . .
H28 H 0.265467 0.682026 0.706528 0.031 Uiso 1 1 calc R U . . .
O22 O 0.40251(6) 0.02244(14) 0.68660(4) 0.0202(2) Uani 1 1 d . . . . .
O23 O 0.27765(5) 0.48590(15) 0.64846(4) 0.0207(2) Uani 1 1 d . . . . .
O25 O 0.58456(6) 0.06936(14) 0.93157(5) 0.0217(2) Uani 1 1 d . . . . .
O14 O 0.69348(6) 0.34704(16) 0.64191(5) 0.0243(2) Uani 1 1 d . . . . .
O27 O 0.63943(6) 0.41248(16) 0.92215(5) 0.0261(2) Uani 1 1 d . . . . .
C8 C 0.53686(7) 0.38015(19) 0.75614(6) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.47697(7) 0.39573(18) 0.79298(6) 0.0145(2) Uani 1 1 d . . . . .
C7 C 0.49481(7) 0.34079(18) 0.85955(6) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.39275(7) 0.48340(18) 0.75263(6) 0.0152(2) Uani 1 1 d . . . . .
C13 C 0.53639(7) 0.54820(19) 0.70764(6) 0.0171(2) Uani 1 1 d . . . . .
H13 H 0.499242 0.674943 0.700015 0.020 Uiso 1 1 calc R U . . .
C24 C 0.58068(8) 0.28405(19) 0.90630(6) 0.0160(2) Uani 1 1 d . . . . .
C17 C 0.37816(7) 0.19882(19) 0.65555(6) 0.0158(2) Uani 1 1 d . . . . .
C3 C 0.35771(7) 0.65843(18) 0.77973(6) 0.0168(2) Uani 1 1 d . . . . .
C11 C 0.64392(8) 0.3468(2) 0.68084(6) 0.0184(2) Uani 1 1 d . . . . .
C16 C 0.34652(7) 0.40399(19) 0.68546(6) 0.0161(2) Uani 1 1 d . . . . .
C9 C 0.59140(8) 0.19513(19) 0.76529(6) 0.0174(2) Uani 1 1 d . . . . .
H9 H 0.592005 0.078066 0.797410 0.021 Uiso 1 1 calc R U . . .
C12 C 0.58921(8) 0.5324(2) 0.67067(6) 0.0196(3) Uani 1 1 d . . . . .
H12 H 0.588245 0.648539 0.638190 0.024 Uiso 1 1 calc R U . . .
C10 C 0.64503(8) 0.1775(2) 0.72857(6) 0.0189(3) Uani 1 1 d . . . . .
H10 H 0.682142 0.050690 0.736055 0.023 Uiso 1 1 calc R U . . .
C6 C 0.42879(8) 0.3479(2) 0.89223(6) 0.0177(2) Uani 1 1 d . . . . .
H6A H 0.448016 0.257205 0.935315 0.021 Uiso 1 1 calc R U . . .
H6B H 0.377428 0.274850 0.860786 0.021 Uiso 1 1 calc R U . . .
C19 C 0.40053(8) 0.0653(2) 0.55504(7) 0.0205(3) Uani 1 1 d . . . . .
H19 H 0.454571 -0.000119 0.585960 0.025 Uiso 1 1 calc R U . . .
C4 C 0.40117(8) 0.7602(2) 0.84886(7) 0.0216(3) Uani 1 1 d . . . . .
H4A H 0.370585 0.899325 0.854039 0.026 Uiso 1 1 calc R U . . .
H4B H 0.457531 0.809136 0.851906 0.026 Uiso 1 1 calc R U . . .
C26 C 0.66508(8) -0.0032(2) 0.97806(7) 0.0256(3) Uani 1 1 d . . . . .
H26A H 0.706656 0.020378 0.956344 0.038 Uiso 1 1 calc R U . . .
H26B H 0.663030 -0.166921 0.988957 0.038 Uiso 1 1 calc R U . . .
H26C H 0.680201 0.087619 1.020438 0.038 Uiso 1 1 calc R U . . .
C15 C 0.75310(9) 0.1643(2) 0.65387(7) 0.0254(3) Uani 1 1 d . . . . .
H15A H 0.786628 0.186974 0.624788 0.038 Uiso 1 1 calc R U . . .
H15B H 0.724019 0.016246 0.642724 0.038 Uiso 1 1 calc R U . . .
H15C H 0.789379 0.164918 0.702287 0.038 Uiso 1 1 calc R U . . .
C5 C 0.40890(9) 0.5942(2) 0.90829(7) 0.0237(3) Uani 1 1 d . . . . .
H5A H 0.453422 0.649053 0.950313 0.028 Uiso 1 1 calc R U . . .
H5B H 0.356111 0.593865 0.917399 0.028 Uiso 1 1 calc R U . . .
C20 C 0.33624(9) -0.1234(2) 0.53204(7) 0.0269(3) Uani 1 1 d . . . . .
H20A H 0.329631 -0.196031 0.572367 0.040 Uiso 1 1 calc R U . . .
H20B H 0.354310 -0.239177 0.505957 0.040 Uiso 1 1 calc R U . . .
H20C H 0.283022 -0.057548 0.502863 0.040 Uiso 1 1 calc R U . . .
C21 C 0.41320(10) 0.1914(2) 0.49593(8) 0.0297(3) Uani 1 1 d . . . . .
H21A H 0.361229 0.266878 0.468167 0.045 Uiso 1 1 calc R U . . .
H21B H 0.429770 0.081357 0.467366 0.045 Uiso 1 1 calc R U . . .
H21C H 0.456820 0.307702 0.513913 0.045 Uiso 1 1 calc R U . . .


_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
O18 C17 1.3275(14) . ?
O18 C19 1.4652(13) . ?
O28 C3 1.3086(15) . ?
O22 C17 1.2039(14) . ?
O23 C16 1.2563(15) . ?
O25 C24 1.3445(14) . ?
O25 C26 1.4444(15) . ?
O14 C11 1.3662(14) . ?
O14 C15 1.4341(15) . ?
O27 C24 1.2041(15) . ?
C8 C9 1.3937(16) . ?
C8 C13 1.4007(16) . ?
C8 C1 1.4863(15) . ?
C1 C7 1.3463(16) . ?
C1 C2 1.4845(16) . ?
C7 C24 1.4908(17) . ?
C7 C6 1.5145(15) . ?
C2 C3 1.3966(15) . ?
C2 C16 1.4190(17) . ?
C13 C12 1.3837(16) . ?
C17 C16 1.5290(15) . ?
C3 C4 1.4889(18) . ?
C11 C10 1.3917(17) . ?
C11 C12 1.3964(16) . ?
C9 C10 1.3922(16) . ?
C6 C5 1.5335(16) . ?
C19 C20 1.5089(18) . ?
C19 C21 1.5104(18) . ?
C4 C5 1.5351(19) . ?

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
C17 O18 C19 117.08(9) . . ?
C24 O25 C26 115.84(10) . . ?
C11 O14 C15 116.93(9) . . ?
C9 C8 C13 117.89(10) . . ?
C9 C8 C1 122.08(10) . . ?
C13 C8 C1 119.93(10) . . ?
C7 C1 C2 119.09(10) . . ?
C7 C1 C8 124.53(11) . . ?
C2 C1 C8 116.37(10) . . ?
C1 C7 C24 122.53(10) . . ?
C1 C7 C6 121.27(11) . . ?
C24 C7 C6 116.09(10) . . ?
C3 C2 C16 117.48(11) . . ?
C3 C2 C1 119.64(11) . . ?
C16 C2 C1 122.83(10) . . ?
C12 C13 C8 121.00(11) . . ?
O27 C24 O25 123.03(12) . . ?
O27 C24 C7 125.76(11) . . ?
O25 C24 C7 111.16(10) . . ?
O22 C17 O18 126.66(11) . . ?
O22 C17 C16 123.38(10) . . ?
O18 C17 C16 109.94(9) . . ?
O28 C3 C2 121.78(11) . . ?
O28 C3 C4 115.78(10) . . ?
C2 C3 C4 122.44(11) . . ?
O14 C11 C10 124.64(11) . . ?
O14 C11 C12 115.89(10) . . ?
C10 C11 C12 119.48(11) . . ?
O23 C16 C2 124.10(10) . . ?
O23 C16 C17 116.04(11) . . ?
C2 C16 C17 119.79(10) . . ?
C10 C9 C8 121.69(11) . . ?
C13 C12 C11 120.37(11) . . ?
C11 C10 C9 119.57(11) . . ?
C7 C6 C5 112.50(9) . . ?
O18 C19 C20 109.79(10) . . ?
O18 C19 C21 104.22(10) . . ?
C20 C19 C21 113.13(12) . . ?
C3 C4 C5 113.59(10) . . ?
C6 C5 C4 111.86(10) . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_cl-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2184544'
loop_
_audit_author_name
_audit_author_address
dfgtr
;FJIRSM
China
;
_audit_update_record             
;
2022-07-07 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2022-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 O5'
_chemical_formula_sum            'C23 H20 O5'
_chemical_formula_weight         376.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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                   8.6573(7)
_cell_length_b                   10.0811(7)
_cell_length_c                   12.3197(11)
_cell_angle_alpha                84.259(7)
_cell_angle_beta                 69.811(8)
_cell_angle_gamma                69.254(7)
_cell_volume                     943.40(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.4360
_cell_measurement_theta_min      4.0700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12253
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.334
_diffrn_reflns_theta_min         4.078
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3960
_reflns_number_total             4188
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0099(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+0.3717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0861
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
1.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C21(H21), C20(H20), C19(H19), C13(H13),
 C22(H22), C12(H12), C14(H14)
1.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
1.d Idealised tetrahedral OH refined as rotating group:
 O28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O27 O 0.52761(9) 0.34682(7) -0.04268(6) 0.01411(16) Uani 1 1 d . . . . .
O10 O 0.92943(9) 0.36904(7) -0.04570(6) 0.01499(16) Uani 1 1 d . . . . .
O28 O 0.75595(9) 0.52102(7) -0.14611(6) 0.01563(16) Uani 1 1 d . . . . .
H28 H 0.676648 0.572397 -0.090321 0.023 Uiso 1 1 calc R U . . .
O24 O 0.53919(10) 0.20059(8) 0.44797(6) 0.01803(17) Uani 1 1 d . . . . .
O26 O 0.35420(10) 0.42631(8) 0.47557(6) 0.02095(18) Uani 1 1 d . . . . .
C4 C 0.59152(12) 0.28108(10) 0.19849(8) 0.01289(19) Uani 1 1 d . . . . .
C11 C 0.90385(12) 0.28185(10) -0.21419(8) 0.01344(19) Uani 1 1 d . . . . .
C23 C 0.47439(13) 0.33273(10) 0.41333(8) 0.0145(2) Uani 1 1 d . . . . .
C15 C 1.09886(13) 0.05094(11) -0.29738(9) 0.0189(2) Uani 1 1 d . . . . .
H15 H 1.178529 -0.040287 -0.290780 0.023 Uiso 1 1 calc R U . . .
C2 C 0.65775(12) 0.34276(10) -0.02111(8) 0.01215(19) Uani 1 1 d . . . . .
C5 C 0.57331(13) 0.35509(10) 0.29068(9) 0.0143(2) Uani 1 1 d . . . . .
C16 C 1.01939(13) 0.14750(11) -0.20466(9) 0.0167(2) Uani 1 1 d . . . . .
H16 H 1.043987 0.121731 -0.134512 0.020 Uiso 1 1 calc R U . . .
C18 C 0.59952(13) 0.05370(11) 0.12867(9) 0.0161(2) Uani 1 1 d . . . . .
H18 H 0.713662 0.042277 0.075995 0.019 Uiso 1 1 calc R U . . .
C21 C 0.26338(14) 0.08941(11) 0.27737(9) 0.0189(2) Uani 1 1 d . . . . .
H21 H 0.147333 0.102295 0.327441 0.023 Uiso 1 1 calc R U . . .
C20 C 0.35702(15) -0.03116(12) 0.20598(9) 0.0207(2) Uani 1 1 d . . . . .
H20 H 0.305944 -0.101163 0.208322 0.025 Uiso 1 1 calc R U . . .
C6 C 0.64095(14) 0.47769(11) 0.27588(9) 0.0186(2) Uani 1 1 d . . . . .
H6A H 0.582187 0.536148 0.348223 0.022 Uiso 1 1 calc R U . . .
H6B H 0.607711 0.537954 0.213386 0.022 Uiso 1 1 calc R U . . .
C8 C 0.94654(14) 0.32010(12) 0.14785(9) 0.0193(2) Uani 1 1 d . . . . .
H8A H 1.062107 0.330531 0.107449 0.023 Uiso 1 1 calc R U . . .
H8B H 0.966842 0.224436 0.181174 0.023 Uiso 1 1 calc R U . . .
C19 C 0.52546(15) -0.04895(11) 0.13124(9) 0.0197(2) Uani 1 1 d . . . . .
H19 H 0.589870 -0.130973 0.082033 0.024 Uiso 1 1 calc R U . . .
C7 C 0.83983(15) 0.43352(13) 0.24694(9) 0.0233(2) Uani 1 1 d . . . . .
H7A H 0.869762 0.395701 0.317177 0.028 Uiso 1 1 calc R U . . .
H7B H 0.874598 0.518588 0.224670 0.028 Uiso 1 1 calc R U . . .
C25 C 0.45167(16) 0.17466(12) 0.56762(9) 0.0238(2) Uani 1 1 d . . . . .
H25A H 0.480847 0.223260 0.618780 0.036 Uiso 1 1 calc R U . . .
H25B H 0.490417 0.072457 0.580953 0.036 Uiso 1 1 calc R U . . .
H25C H 0.324677 0.210766 0.583894 0.036 Uiso 1 1 calc R U . . .
C9 C 0.85502(13) 0.33291(10) 0.06281(8) 0.0144(2) Uani 1 1 d . . . . .
C13 C 0.94541(15) 0.22127(12) -0.40923(9) 0.0227(2) Uani 1 1 d . . . . .
H13 H 0.919757 0.246322 -0.479088 0.027 Uiso 1 1 calc R U . . .
C17 C 0.50860(13) 0.17360(10) 0.20245(8) 0.0133(2) Uani 1 1 d . . . . .
C22 C 0.33792(13) 0.19135(11) 0.27620(9) 0.0157(2) Uani 1 1 d . . . . .
H22 H 0.272901 0.273197 0.325557 0.019 Uiso 1 1 calc R U . . .
C3 C 0.69976(13) 0.31192(10) 0.08380(8) 0.0133(2) Uani 1 1 d . . . . .
C12 C 0.86597(14) 0.31871(11) -0.31668(9) 0.0187(2) Uani 1 1 d . . . . .
H12 H 0.786298 0.409900 -0.323367 0.022 Uiso 1 1 calc R U . . .
C1 C 0.80955(12) 0.38345(10) -0.11131(8) 0.0131(2) Uani 1 1 d . . . . .
C14 C 1.06185(14) 0.08777(12) -0.39994(9) 0.0205(2) Uani 1 1 d . . . . .
H14 H 1.116075 0.021801 -0.463342 0.025 Uiso 1 1 calc R U . . .


_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
O27 C2 1.2302(12) . ?
O10 C9 1.3450(12) . ?
O10 C1 1.4833(11) . ?
O28 H28 0.8400 . ?
O28 C1 1.3730(12) . ?
O24 C23 1.3391(12) . ?
O24 C25 1.4517(12) . ?
O26 C23 1.2080(13) . ?
C4 C5 1.3542(14) . ?
C4 C17 1.4861(13) . ?
C4 C3 1.4750(13) . ?
C11 C16 1.3921(14) . ?
C11 C12 1.3948(14) . ?
C11 C1 1.5084(13) . ?
C23 C5 1.4976(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.3897(15) . ?
C15 C14 1.3921(16) . ?
C2 C3 1.4365(13) . ?
C2 C1 1.5533(13) . ?
C5 C6 1.5158(13) . ?
C16 H16 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.3901(14) . ?
C18 C17 1.3996(14) . ?
C21 H21 0.9500 . ?
C21 C20 1.3899(16) . ?
C21 C22 1.3904(14) . ?
C20 H20 0.9500 . ?
C20 C19 1.3883(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5345(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5503(16) . ?
C8 C9 1.4884(13) . ?
C19 H19 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C9 C3 1.3671(13) . ?
C13 H13 0.9500 . ?
C13 C12 1.3936(15) . ?
C13 C14 1.3886(16) . ?
C17 C22 1.3998(14) . ?
C22 H22 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14 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
C9 O10 C1 107.93(7) . . ?
C1 O28 H28 109.5 . . ?
C23 O24 C25 115.07(8) . . ?
C5 C4 C17 125.64(9) . . ?
C5 C4 C3 117.30(9) . . ?
C3 C4 C17 117.04(8) . . ?
C16 C11 C12 119.78(9) . . ?
C16 C11 C1 120.18(9) . . ?
C12 C11 C1 119.89(9) . . ?
O24 C23 C5 112.87(8) . . ?
O26 C23 O24 123.87(9) . . ?
O26 C23 C5 123.18(9) . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 120.07(10) . . ?
C14 C15 H15 120.0 . . ?
O27 C2 C3 130.98(9) . . ?
O27 C2 C1 122.17(8) . . ?
C3 C2 C1 106.76(8) . . ?
C4 C5 C23 124.15(9) . . ?
C4 C5 C6 121.57(9) . . ?
C23 C5 C6 114.11(8) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.24(9) . . ?
C15 C16 H16 119.9 . . ?
C19 C18 H18 119.5 . . ?
C19 C18 C17 121.04(10) . . ?
C17 C18 H18 119.5 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.63(10) . . ?
C22 C21 H21 119.7 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.77(9) . . ?
C19 C20 H20 120.1 . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C5 C6 C7 114.59(9) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C9 C8 C7 112.05(9) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.76(10) . . ?
C20 C19 H19 120.1 . . ?
C6 C7 C8 113.49(8) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O10 C9 C8 118.05(8) . . ?
O10 C9 C3 115.62(8) . . ?
C3 C9 C8 126.33(9) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.39(10) . . ?
C18 C17 C4 119.90(9) . . ?
C18 C17 C22 118.63(9) . . ?
C22 C17 C4 121.45(9) . . ?
C21 C22 C17 120.13(10) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C2 C3 C4 128.55(9) . . ?
C9 C3 C4 124.15(9) . . ?
C9 C3 C2 106.89(8) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.76(10) . . ?
C13 C12 H12 120.1 . . ?
O10 C1 C11 109.25(7) . . ?
O10 C1 C2 102.72(7) . . ?
O28 C1 O10 108.93(7) . . ?
O28 C1 C11 110.82(8) . . ?
O28 C1 C2 112.77(8) . . ?
C11 C1 C2 111.98(8) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.77(10) . . ?
C13 C14 H14 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20220602CL-2_autored
_database_code_depnum_ccdc_archive 'CCDC 2184326'
loop_
_audit_author_name
_audit_author_address
abcccc
;FJIRSM
China
;
_audit_update_record             
;
2022-07-06 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2022-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N0 O3'
_chemical_formula_sum            'C21 H18 N0 O3'
_chemical_formula_weight         318.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.44830(10)
_cell_length_b                   9.97000(10)
_cell_length_c                   9.7662(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.501(2)
_cell_angle_gamma                90
_cell_volume                     808.48(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    28096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.4560
_cell_measurement_theta_min      4.4640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33268
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.433
_diffrn_reflns_theta_min         4.479
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3538
_reflns_number_total             3678
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.0804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
1.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C24(H24), C23(H23), C20(H20), C21(H21), C22(H22),
 C13(H13), C14(H14), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O17 O 0.34242(15) 0.47347(14) 1.02271(14) 0.0241(3) Uani 1 1 d . . . . .
O18 O 0.33867(15) 0.30393(16) 0.40251(15) 0.0291(3) Uani 1 1 d . . . . .
C9 C 0.38018(19) 0.32625(19) 0.5380(2) 0.0208(4) Uani 1 1 d . . . . .
C6 C 0.34453(18) 0.39193(18) 0.79575(19) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.1353(2) 0.65041(18) 0.6920(2) 0.0200(4) Uani 1 1 d . . . . .
H11 H 0.073913 0.576024 0.694807 0.024 Uiso 1 1 calc R U . . .
C7 C 0.35154(18) 0.49301(17) 0.70944(19) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.28523(19) 0.62954(18) 0.69875(19) 0.0171(3) Uani 1 1 d . . . . .
C16 C 0.28339(18) 0.39749(17) 0.91214(19) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.3722(2) 0.74044(19) 0.6916(2) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.473010 0.727184 0.694041 0.026 Uiso 1 1 calc R U . . .
C2 C 0.62484(19) 0.45762(18) 0.7167(2) 0.0200(4) Uani 1 1 d . . . . .
H2A H 0.670127 0.399083 0.665308 0.024 Uiso 1 1 calc R U . . .
H2B H 0.668053 0.549099 0.722303 0.024 Uiso 1 1 calc R U . . .
C24 C 0.1407(2) 0.25813(18) 1.0210(2) 0.0207(3) Uani 1 1 d . . . . .
H24 H 0.209134 0.294931 1.120853 0.025 Uiso 1 1 calc R U . . .
C19 C 0.15546(19) 0.29928(17) 0.89140(19) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.0257(2) 0.16345(19) 1.0029(2) 0.0248(4) Uani 1 1 d . . . . .
H23 H 0.016354 0.134624 1.090984 0.030 Uiso 1 1 calc R U . . .
C3 C 0.68043(19) 0.40647(19) 0.8818(2) 0.0218(4) Uani 1 1 d . . . . .
H3A H 0.799264 0.398447 0.935776 0.026 Uiso 1 1 calc R U . . .
H3B H 0.651411 0.473604 0.938865 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4246(2) 0.26199(17) 0.7912(2) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.385892 0.189466 0.835903 0.022 Uiso 1 1 calc R U . . .
C20 C 0.05223(19) 0.24650(19) 0.7449(2) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.061682 0.274110 0.656480 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6085(2) 0.27151(18) 0.8891(2) 0.0217(4) Uani 1 1 d . . . . .
H4A H 0.638675 0.252322 0.999084 0.026 Uiso 1 1 calc R U . . .
H4B H 0.657538 0.200999 0.853724 0.026 Uiso 1 1 calc R U . . .
C1 C 0.43744(19) 0.46151(18) 0.6148(2) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.408131 0.531277 0.532080 0.021 Uiso 1 1 calc R U . . .
O1 O 0.37818(14) 0.22683(13) 0.62929(15) 0.0223(3) Uani 1 1 d . . . . .
C21 C -0.0645(2) 0.1535(2) 0.7282(2) 0.0255(4) Uani 1 1 d . . . . .
H21 H -0.136623 0.119303 0.627891 0.031 Uiso 1 1 calc R U . . .
C22 C -0.0759(2) 0.11050(19) 0.8571(2) 0.0252(4) Uani 1 1 d . . . . .
H22 H -0.153446 0.044651 0.845875 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1653(2) 0.8893(2) 0.6763(2) 0.0282(4) Uani 1 1 d . . . . .
H13 H 0.124927 0.977671 0.669692 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3131(2) 0.86936(19) 0.6809(2) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.373434 0.943983 0.676739 0.032 Uiso 1 1 calc R U . . .
C12 C 0.0765(2) 0.7801(2) 0.6813(2) 0.0258(4) Uani 1 1 d . . . . .
H12 H -0.024811 0.794019 0.677356 0.031 Uiso 1 1 calc R U . . .


_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
O17 C16 1.215(2) . ?
O18 C9 1.208(2) . ?
C9 C1 1.512(2) . ?
C9 O1 1.339(2) . ?
C6 C7 1.336(2) . ?
C6 C16 1.502(2) . ?
C6 C5 1.512(2) . ?
C11 C10 1.402(2) . ?
C11 C12 1.391(3) . ?
C7 C10 1.481(2) . ?
C7 C1 1.525(2) . ?
C10 C15 1.399(2) . ?
C16 C19 1.492(2) . ?
C15 C14 1.386(3) . ?
C2 C3 1.526(2) . ?
C2 C1 1.564(2) . ?
C24 C19 1.399(2) . ?
C24 C23 1.386(3) . ?
C19 C20 1.394(2) . ?
C23 C22 1.387(3) . ?
C3 C4 1.524(2) . ?
C5 C4 1.535(2) . ?
C5 O1 1.467(2) . ?
C20 C21 1.390(2) . ?
C21 C22 1.382(3) . ?
C13 C14 1.390(3) . ?
C13 C12 1.389(3) . ?

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
O18 C9 C1 124.04(18) . . ?
O18 C9 O1 119.50(17) . . ?
O1 C9 C1 116.46(14) . . ?
C7 C6 C16 127.06(16) . . ?
C7 C6 C5 116.86(14) . . ?
C16 C6 C5 115.64(15) . . ?
C12 C11 C10 119.98(17) . . ?
C6 C7 C10 126.24(15) . . ?
C6 C7 C1 115.33(15) . . ?
C10 C7 C1 118.42(15) . . ?
C11 C10 C7 121.58(15) . . ?
C15 C10 C11 119.01(16) . . ?
C15 C10 C7 119.39(14) . . ?
O17 C16 C6 121.09(15) . . ?
O17 C16 C19 121.89(15) . . ?
C19 C16 C6 116.89(14) . . ?
C14 C15 C10 120.74(16) . . ?
C3 C2 C1 113.25(14) . . ?
C23 C24 C19 119.69(17) . . ?
C24 C19 C16 119.58(15) . . ?
C20 C19 C16 120.77(15) . . ?
C20 C19 C24 119.65(16) . . ?
C24 C23 C22 120.45(17) . . ?
C4 C3 C2 114.09(15) . . ?
C6 C5 C4 111.25(14) . . ?
O1 C5 C6 109.87(13) . . ?
O1 C5 C4 110.69(13) . . ?
C21 C20 C19 119.97(16) . . ?
C3 C4 C5 115.00(14) . . ?
C9 C1 C7 108.43(14) . . ?
C9 C1 C2 108.78(13) . . ?
C7 C1 C2 112.83(14) . . ?
C9 O1 C5 116.63(13) . . ?
C22 C21 C20 120.16(17) . . ?
C21 C22 C23 120.04(17) . . ?
C12 C13 C14 120.05(17) . . ?
C15 C14 C13 119.88(17) . . ?
C13 C12 C11 120.32(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20220602-CL-3_autored
_database_code_depnum_ccdc_archive 'CCDC 2184475'
loop_
_audit_author_name
_audit_author_address
aaaaa
;FJIRSM
China
;
_audit_update_record             
;
2022-07-06 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O4'
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.593
_cell_length_b                   15.25490(10)
_cell_length_c                   17.53070(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.1820(10)
_cell_angle_gamma                90
_cell_volume                     1760.442(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38509
_cell_measurement_theta_min      3.3280
_cell_measurement_theta_max      60.3770

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.464
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.3405
_diffrn_radiation_type           GaK\a
_diffrn_source                   'micro-focus metaljet'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            69133
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.341
_diffrn_reflns_theta_max         60.478
_diffrn_reflns_theta_full        53.543
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4034
_reflns_number_gt                3547
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0489P)²+0.5929P] 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_number_reflns         4034
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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
O17 O 0.63169(12) 0.60172(5) 0.46869(5) 0.02005(18) Uani 1 1 d . . . . .
O15 O 0.26499(12) 0.96527(5) 0.61951(4) 0.02162(18) Uani 1 1 d . . . . .
O20 O 0.15842(12) 0.94508(5) 0.48128(5) 0.02317(18) Uani 1 1 d . . . . .
H20 H 0.158247 0.966294 0.525491 0.035 Uiso 1 1 calc R U . . .
O19 O 0.93871(12) 0.66618(6) 0.47723(5) 0.02482(19) Uani 1 1 d . . . . .
C16 C 0.75574(16) 0.67091(7) 0.47846(6) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.51896(15) 0.76970(7) 0.54425(6) 0.0154(2) Uani 1 1 d . . . . .
C7 C 0.40041(16) 0.85257(7) 0.54564(6) 0.0162(2) Uani 1 1 d . . . . .
C2 C 0.64276(15) 0.75458(7) 0.48687(6) 0.0165(2) Uani 1 1 d . . . . .
C8 C 0.48513(16) 0.70700(7) 0.60744(6) 0.0154(2) Uani 1 1 d . . . . .
C9 C 0.28818(16) 0.69442(7) 0.63128(6) 0.0181(2) Uani 1 1 d . . . . .
H9 H 0.177479 0.724348 0.605932 0.022 Uiso 1 1 calc R U . . .
C6 C 0.28331(16) 0.87726(7) 0.48134(6) 0.0179(2) Uani 1 1 d . . . . .
C21 C 0.55397(16) 0.89527(7) 0.67683(6) 0.0172(2) Uani 1 1 d . . . . .
C5 C 0.28896(17) 0.82953(8) 0.40718(6) 0.0199(2) Uani 1 1 d . . . . .
H5A H 0.180900 0.852915 0.371324 0.024 Uiso 1 1 calc R U . . .
H5B H 0.259702 0.766752 0.415736 0.024 Uiso 1 1 calc R U . . .
C13 C 0.64507(16) 0.66223(7) 0.64563(6) 0.0179(2) Uani 1 1 d . . . . .
H13 H 0.779717 0.670034 0.630147 0.022 Uiso 1 1 calc R U . . .
C22 C 0.49988(17) 0.90123(7) 0.75267(6) 0.0211(2) Uani 1 1 d . . . . .
H22 H 0.362750 0.912551 0.763540 0.025 Uiso 1 1 calc R U . . .
C14 C 0.39635(16) 0.90627(7) 0.61343(6) 0.0169(2) Uani 1 1 d . . . . .
C26 C 0.75698(17) 0.88175(7) 0.66141(6) 0.0201(2) Uani 1 1 d . . . . .
H26 H 0.795478 0.878765 0.610053 0.024 Uiso 1 1 calc R U . . .
C12 C 0.60946(17) 0.60637(7) 0.70606(6) 0.0206(2) Uani 1 1 d . . . . .
H12 H 0.719560 0.576011 0.731375 0.025 Uiso 1 1 calc R U . . .
C10 C 0.25319(17) 0.63849(8) 0.69172(6) 0.0211(2) Uani 1 1 d . . . . .
H10 H 0.118652 0.630195 0.707148 0.025 Uiso 1 1 calc R U . . .
C11 C 0.41302(18) 0.59471(7) 0.72967(6) 0.0214(2) Uani 1 1 d . . . . .
H11 H 0.388799 0.557109 0.771392 0.026 Uiso 1 1 calc R U . . .
C4 C 0.49505(17) 0.83771(8) 0.37041(6) 0.0204(2) Uani 1 1 d . . . . .
H4A H 0.504501 0.896463 0.346895 0.024 Uiso 1 1 calc R U . . .
H4B H 0.501473 0.793605 0.329186 0.024 Uiso 1 1 calc R U . . .
C3 C 0.67829(16) 0.82454(7) 0.42790(6) 0.0194(2) Uani 1 1 d . . . . .
H3A H 0.798548 0.808308 0.399579 0.023 Uiso 1 1 calc R U . . .
H3B H 0.708695 0.880717 0.454407 0.023 Uiso 1 1 calc R U . . .
C24 C 0.84701(18) 0.87656(8) 0.79621(7) 0.0237(2) Uani 1 1 d . . . . .
H24 H 0.946975 0.869533 0.836906 0.028 Uiso 1 1 calc R U . . .
C25 C 0.90274(17) 0.87267(8) 0.72118(7) 0.0239(2) Uani 1 1 d . . . . .
H25 H 1.041017 0.863756 0.710629 0.029 Uiso 1 1 calc R U . . .
C23 C 0.64574(19) 0.89069(8) 0.81208(6) 0.0241(2) Uani 1 1 d . . . . .
H23 H 0.607910 0.893135 0.863541 0.029 Uiso 1 1 calc R U . . .
C18 C 0.72967(19) 0.51764(8) 0.46007(8) 0.0287(3) Uani 1 1 d . . . . .
H18A H 0.830052 0.522127 0.421070 0.043 Uiso 1 1 calc R U . . .
H18B H 0.627494 0.473555 0.444451 0.043 Uiso 1 1 calc R U . . .
H18C H 0.797776 0.500310 0.508861 0.043 Uiso 1 1 calc R U . . .


_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
O17 C16 1.3404(13) . ?
O17 C18 1.4478(14) . ?
O15 C14 1.2577(13) . ?
O20 C6 1.3222(13) . ?
O19 C16 1.2098(13) . ?
C16 C2 1.4893(15) . ?
C1 C2 1.3500(14) . ?
C1 C7 1.4872(14) . ?
C1 C8 1.4897(14) . ?
C7 C6 1.3826(15) . ?
C7 C14 1.4447(15) . ?
C2 C3 1.5131(14) . ?
C8 C13 1.3957(15) . ?
C8 C9 1.3991(14) . ?
C9 C10 1.3896(16) . ?
C6 C5 1.4925(15) . ?
C21 C26 1.3953(15) . ?
C21 C22 1.3985(15) . ?
C21 C14 1.4883(15) . ?
C5 C4 1.5408(15) . ?
C13 C12 1.3897(15) . ?
C22 C23 1.3871(16) . ?
C26 C25 1.3888(16) . ?
C12 C11 1.3926(16) . ?
C10 C11 1.3860(16) . ?
C4 C3 1.5427(15) . ?
C24 C25 1.3865(17) . ?
C24 C23 1.3876(17) . ?

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
C16 O17 C18 116.00(9) . . ?
O19 C16 O17 123.55(10) . . ?
O19 C16 C2 123.88(10) . . ?
O17 C16 C2 112.50(9) . . ?
C2 C1 C7 119.83(9) . . ?
C2 C1 C8 124.48(10) . . ?
C7 C1 C8 115.67(9) . . ?
C6 C7 C14 118.76(10) . . ?
C6 C7 C1 119.23(9) . . ?
C14 C7 C1 121.94(9) . . ?
C1 C2 C16 123.13(10) . . ?
C1 C2 C3 120.76(10) . . ?
C16 C2 C3 116.08(9) . . ?
C13 C8 C9 118.59(10) . . ?
C13 C8 C1 122.04(9) . . ?
C9 C8 C1 119.33(9) . . ?
C10 C9 C8 120.53(10) . . ?
O20 C6 C7 122.23(10) . . ?
O20 C6 C5 115.25(9) . . ?
C7 C6 C5 122.51(10) . . ?
C26 C21 C22 119.45(10) . . ?
C26 C21 C14 120.63(10) . . ?
C22 C21 C14 119.89(10) . . ?
C6 C5 C4 112.96(9) . . ?
C12 C13 C8 120.70(10) . . ?
C23 C22 C21 120.23(11) . . ?
O15 C14 C7 121.31(10) . . ?
O15 C14 C21 118.22(9) . . ?
C7 C14 C21 120.42(9) . . ?
C25 C26 C21 119.97(10) . . ?
C13 C12 C11 120.27(10) . . ?
C11 C10 C9 120.52(10) . . ?
C10 C11 C12 119.38(10) . . ?
C5 C4 C3 113.13(9) . . ?
C2 C3 C4 113.13(9) . . ?
C25 C24 C23 120.23(11) . . ?
C24 C25 C26 120.19(11) . . ?
C22 C23 C24 119.89(11) . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043

