# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_1017oy685_0m
_database_code_depnum_ccdc_archive 'CCDC 2086128'
loop_
_audit_author_name
_audit_author_address
'Liyao Zheng'
;Guangzhou University
China
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 O3'
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.35
_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 0.0033 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'

_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                   9.1743(5)
_cell_length_b                   9.2287(5)
_cell_length_c                   11.7068(6)
_cell_angle_alpha                71.616(2)
_cell_angle_beta                 68.548(2)
_cell_angle_gamma                85.269(2)
_cell_volume                     874.83(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.202
_cell_measurement_theta_min      2.487
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0690 before and 0.0523 after correction. The Ratio of minimum to maximum transmission is 0.8865. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10866
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.488
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2396
_reflns_number_total             3979
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3979
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.033
_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)+(0.0576P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C6(H6), C11(H11), C18(H18), C13(H13), C2(H2A), C20(H20), C21(H21),
 C19(H19), C3(H3), C5(H5), C4(H4)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.58455(16) 0.83830(15) 0.02286(14) 0.0557(4) Uani 1 1 d . . . . .
O3 O 0.53036(17) 0.29583(14) 0.33301(14) 0.0535(4) Uani 1 1 d . . . . .
O2 O 0.33127(17) 0.87029(17) 0.05887(19) 0.0737(5) Uani 1 1 d . . . . .
H2 H 0.360450 0.960541 0.026890 0.111 Uiso 1 1 calc GR . . . .
C9 C 0.4902(2) 0.5278(2) 0.20698(18) 0.0422(4) Uani 1 1 d . . . . .
C17 C 0.6855(2) 0.6903(2) 0.24055(18) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.6059(2) 0.5470(2) 0.25938(18) 0.0415(4) Uani 1 1 d . . . . .
C16 C 0.4504(2) 0.7862(2) 0.06575(19) 0.0466(5) Uani 1 1 d . . . . .
C22 C 0.8463(2) 0.7114(2) 0.1835(2) 0.0509(5) Uani 1 1 d . . . . .
H22 H 0.906578 0.633184 0.158188 0.061 Uiso 1 1 calc R . . . .
C14 C 0.4112(2) 0.6206(2) 0.12951(19) 0.0448(5) Uani 1 1 d . . . . .
C1 C 0.7149(2) 0.3452(2) 0.41796(19) 0.0485(5) Uani 1 1 d . . . . .
C10 C 0.4473(2) 0.3725(2) 0.25689(19) 0.0478(5) Uani 1 1 d . . . . .
C6 C 0.7580(3) 0.4365(3) 0.4760(2) 0.0561(6) Uani 1 1 d . . . . .
H6 H 0.732441 0.538740 0.459172 0.067 Uiso 1 1 calc R . . . .
C11 C 0.3344(3) 0.3058(2) 0.2365(2) 0.0556(5) Uani 1 1 d . . . . .
H11 H 0.312076 0.201146 0.271565 0.067 Uiso 1 1 calc R . . . .
C18 C 0.5986(3) 0.8083(2) 0.2777(2) 0.0512(5) Uani 1 1 d . . . . .
H18 H 0.490087 0.796254 0.316429 0.061 Uiso 1 1 calc R . . . .
C7 C 0.6242(2) 0.4056(2) 0.33422(19) 0.0456(5) Uani 1 1 d . . . . .
C13 C 0.2946(2) 0.5547(2) 0.1108(2) 0.0514(5) Uani 1 1 d . . . . .
H13 H 0.240513 0.617262 0.061515 0.062 Uiso 1 1 calc R . . . .
C12 C 0.2550(2) 0.3986(3) 0.1626(2) 0.0543(5) Uani 1 1 d . . . . .
C2 C 0.7528(3) 0.1916(2) 0.4465(2) 0.0598(6) Uani 1 1 d . . . . .
H2A H 0.722691 0.128292 0.410316 0.072 Uiso 1 1 calc R . . . .
C20 C 0.6715(3) 0.9439(3) 0.2577(2) 0.0660(6) Uani 1 1 d . . . . .
H20 H 0.611963 1.022275 0.283523 0.079 Uiso 1 1 calc R . . . .
C21 C 0.9192(3) 0.8476(3) 0.1635(2) 0.0629(6) Uani 1 1 d . . . . .
H21 H 1.027709 0.860203 0.125483 0.076 Uiso 1 1 calc R . . . .
C15 C 0.1275(3) 0.3330(3) 0.1385(3) 0.0706(7) Uani 1 1 d . . . . .
H15A H 0.156201 0.234386 0.127832 0.106 Uiso 1 1 calc GR . . . .
H15B H 0.114098 0.399940 0.061758 0.106 Uiso 1 1 calc GR . . . .
H15C H 0.031010 0.323032 0.210564 0.106 Uiso 1 1 calc GR . . . .
C19 C 0.8308(3) 0.9637(3) 0.2000(2) 0.0685(7) Uani 1 1 d . . . . .
H19 H 0.879131 1.055817 0.185622 0.082 Uiso 1 1 calc R . . . .
C3 C 0.8346(3) 0.1335(3) 0.5279(3) 0.0764(8) Uani 1 1 d . . . . .
H3 H 0.860771 0.031380 0.545134 0.092 Uiso 1 1 calc R . . . .
C5 C 0.8390(3) 0.3751(3) 0.5587(2) 0.0714(7) Uani 1 1 d . . . . .
H5 H 0.867133 0.436435 0.597464 0.086 Uiso 1 1 calc R . . . .
C4 C 0.8782(3) 0.2240(4) 0.5839(3) 0.0829(8) Uani 1 1 d . . . . .
H4 H 0.933845 0.183625 0.638492 0.100 Uiso 1 1 calc R . . . .


_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 C16 1.221(2) . ?
O3 C10 1.373(2) . ?
O3 C7 1.390(2) . ?
O2 H2 0.8200 . ?
O2 C16 1.299(2) . ?
C9 C8 1.452(3) . ?
C9 C14 1.404(3) . ?
C9 C10 1.395(3) . ?
C17 C8 1.479(3) . ?
C17 C22 1.380(3) . ?
C17 C18 1.383(3) . ?
C8 C7 1.360(3) . ?
C16 C14 1.482(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.385(3) . ?
C14 C13 1.387(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.463(3) . ?
C1 C2 1.395(3) . ?
C10 C11 1.373(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C20 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.396(3) . ?
C12 C15 1.511(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.367(3) . ?
C21 H21 0.9300 . ?
C21 C19 1.371(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 H19 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.371(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(4) . ?
C4 H4 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
C10 O3 C7 106.19(14) . . ?
C16 O2 H2 109.5 . . ?
C14 C9 C8 137.75(17) . . ?
C10 C9 C8 105.79(16) . . ?
C10 C9 C14 116.37(18) . . ?
C22 C17 C8 121.50(17) . . ?
C22 C17 C18 118.38(18) . . ?
C18 C17 C8 120.11(17) . . ?
C9 C8 C17 127.99(16) . . ?
C7 C8 C9 106.09(16) . . ?
C7 C8 C17 125.89(17) . . ?
O1 C16 O2 123.08(18) . . ?
O1 C16 C14 122.21(17) . . ?
O2 C16 C14 114.71(17) . . ?
C17 C22 H22 119.5 . . ?
C17 C22 C21 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C9 C14 C16 121.89(17) . . ?
C13 C14 C9 118.93(18) . . ?
C13 C14 C16 119.18(18) . . ?
C6 C1 C7 121.14(18) . . ?
C6 C1 C2 118.7(2) . . ?
C2 C1 C7 120.10(19) . . ?
O3 C10 C9 110.40(17) . . ?
C11 C10 O3 124.52(18) . . ?
C11 C10 C9 125.05(19) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C10 C11 H11 120.9 . . ?
C10 C11 C12 118.11(19) . . ?
C12 C11 H11 120.9 . . ?
C17 C18 H18 119.7 . . ?
C20 C18 C17 120.6(2) . . ?
C20 C18 H18 119.7 . . ?
O3 C7 C1 113.75(16) . . ?
C8 C7 O3 111.49(16) . . ?
C8 C7 C1 134.71(18) . . ?
C14 C13 H13 118.5 . . ?
C14 C13 C12 122.9(2) . . ?
C12 C13 H13 118.5 . . ?
C11 C12 C13 118.61(19) . . ?
C11 C12 C15 120.8(2) . . ?
C13 C12 C15 120.6(2) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2A 119.9 . . ?
C18 C20 H20 119.8 . . ?
C19 C20 C18 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C22 C21 H21 120.1 . . ?
C19 C21 C22 119.7(2) . . ?
C19 C21 H21 120.1 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20 C19 C21 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C21 C19 H19 120.0 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?

_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_811_0m
_database_code_depnum_ccdc_archive 'CCDC 2086131'
loop_
_audit_author_name
_audit_author_address
'Liyao Zheng'
;Guangzhou University
China
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_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 0.0033 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'

_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                   4.627(2)
_cell_length_b                   7.831(3)
_cell_length_c                   17.418(6)
_cell_angle_alpha                79.477(11)
_cell_angle_beta                 87.815(12)
_cell_angle_gamma                77.297(12)
_cell_volume                     605.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.005
_cell_measurement_theta_min      2.716
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1063 before and 0.0766 after correction. The Ratio of minimum to maximum transmission is 0.6742. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5990
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.107
_diffrn_reflns_theta_max         25.107
_diffrn_reflns_theta_min         2.710
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1366
_reflns_number_total             2141
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0717
_refine_ls_restrained_S_all      1.034
_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)+(0.0946P)²+0.3670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.2182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.4401(5) 0.3121(2) 0.24570(12) 0.0459(6) Uani 1 1 d . . . . .
O3 O -0.0427(5) 0.9503(3) 0.26383(13) 0.0511(7) Uani 1 1 d . . . . .
H3 H -0.085321 1.037620 0.287079 0.077 Uiso 1 1 calc GR . . . .
O2 O 0.7763(5) 0.2349(3) 0.33911(13) 0.0553(7) Uani 1 1 d . . . . .
C3 C 0.2519(6) 0.6538(3) 0.28026(16) 0.0333(7) Uani 1 1 d . . . . .
C4 C 0.4793(6) 0.5291(3) 0.32490(17) 0.0356(7) Uani 1 1 d . . . . .
C6 C 0.6213(7) 0.5666(4) 0.38784(17) 0.0425(8) Uani 1 1 d . . . . .
H6 H 0.771900 0.477393 0.416100 0.051 Uiso 1 1 calc R . . . .
C9 C 0.1749(7) 0.8228(4) 0.30378(17) 0.0386(7) Uani 1 1 d . . . . .
C2 C 0.1176(6) 0.6009(4) 0.21580(17) 0.0358(7) Uani 1 1 d . . . . .
C8 C 0.3195(7) 0.8583(4) 0.36547(18) 0.0413(8) Uani 1 1 d . . . . .
H8 H 0.263980 0.973316 0.378861 0.050 Uiso 1 1 calc R . . . .
C7 C 0.5432(7) 0.7323(4) 0.40879(18) 0.0418(8) Uani 1 1 d . . . . .
C5 C 0.5778(7) 0.3522(4) 0.30531(18) 0.0422(8) Uani 1 1 d . . . . .
C1 C 0.2138(7) 0.4343(4) 0.20152(18) 0.0408(8) Uani 1 1 d . . . . .
C13 C 0.1169(8) 0.3448(4) 0.1405(2) 0.0532(9) Uani 1 1 d . . . . .
H13A H -0.058493 0.424855 0.112754 0.064 Uiso 1 1 calc R . . . .
H13B H 0.056094 0.234997 0.166737 0.064 Uiso 1 1 calc R . . . .
C12 C 0.0182(8) 0.8476(4) 0.0984(2) 0.0582(10) Uani 1 1 d . . . . .
H12A H -0.140323 0.931485 0.066749 0.087 Uiso 1 1 calc GR . . . .
H12B H 0.145419 0.774043 0.065199 0.087 Uiso 1 1 calc GR . . . .
H12C H 0.136391 0.913731 0.122286 0.087 Uiso 1 1 calc GR . . . .
C11 C -0.1177(7) 0.7283(4) 0.16257(19) 0.0454(8) Uani 1 1 d . . . . .
H11A H -0.256070 0.803409 0.193953 0.054 Uiso 1 1 calc R . . . .
H11B H -0.232517 0.659258 0.138287 0.054 Uiso 1 1 calc R . . . .
C10 C 0.6895(8) 0.7772(5) 0.4765(2) 0.0575(10) Uani 1 1 d . . . . .
H10A H 0.550791 0.783912 0.520315 0.086 Uiso 1 1 calc GR . . . .
H10B H 0.745483 0.892069 0.460323 0.086 Uiso 1 1 calc GR . . . .
H10C H 0.867011 0.684578 0.492610 0.086 Uiso 1 1 calc GR . . . .
C14 C 0.3536(10) 0.2972(6) 0.0815(2) 0.0834(14) Uani 1 1 d . . . . .
H14A H 0.411257 0.405584 0.054091 0.125 Uiso 1 1 calc GR . . . .
H14B H 0.277034 0.239421 0.043727 0.125 Uiso 1 1 calc GR . . . .
H14C H 0.526676 0.215820 0.108266 0.125 Uiso 1 1 calc GR . . . .


_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 1.357(4) . ?
O1 C1 1.398(3) . ?
O3 H3 0.8400 . ?
O3 C9 1.361(3) . ?
O2 C5 1.227(3) . ?
C3 C4 1.413(4) . ?
C3 C9 1.424(4) . ?
C3 C2 1.467(4) . ?
C4 C6 1.406(4) . ?
C4 C5 1.458(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C9 C8 1.387(4) . ?
C2 C1 1.349(4) . ?
C2 C11 1.517(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.397(4) . ?
C7 C10 1.513(4) . ?
C1 C13 1.507(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.506(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C11 1.530(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 C1 122.7(2) . . ?
C9 O3 H3 109.5 . . ?
C4 C3 C9 114.8(3) . . ?
C4 C3 C2 119.1(3) . . ?
C9 C3 C2 126.1(3) . . ?
C3 C4 C5 119.4(3) . . ?
C6 C4 C3 123.4(3) . . ?
C6 C4 C5 117.2(3) . . ?
C4 C6 H6 119.8 . . ?
C7 C6 C4 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
O3 C9 C3 118.5(3) . . ?
O3 C9 C8 120.5(3) . . ?
C8 C9 C3 121.0(3) . . ?
C3 C2 C11 122.7(2) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 C11 118.5(3) . . ?
C9 C8 H8 118.5 . . ?
C9 C8 C7 122.9(3) . . ?
C7 C8 H8 118.5 . . ?
C6 C7 C8 117.4(3) . . ?
C6 C7 C10 121.9(3) . . ?
C8 C7 C10 120.7(3) . . ?
O1 C5 C4 118.2(3) . . ?
O2 C5 O1 116.9(3) . . ?
O2 C5 C4 124.9(3) . . ?
O1 C1 C13 108.0(2) . . ?
C2 C1 O1 121.8(3) . . ?
C2 C1 C13 130.2(3) . . ?
C1 C13 H13A 108.9 . . ?
C1 C13 H13B 108.9 . . ?
C1 C13 C14 113.5(3) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
C2 C11 C12 111.8(3) . . ?
C2 C11 H11A 109.3 . . ?
C2 C11 H11B 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_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_zz
_database_code_depnum_ccdc_archive 'CCDC 2086130'
loop_
_audit_author_name
_audit_author_address
'Liyao Zheng'
;Guangzhou University
China
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Cl O4'
_chemical_formula_sum            'C23 H17 Cl O4'
_chemical_formula_weight         392.82
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9608(17)
_cell_length_b                   5.8335(7)
_cell_length_c                   26.640(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.150(8)
_cell_angle_gamma                90
_cell_volume                     1858.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2442
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.578
_cell_measurement_theta_min      2.288
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1201 before and 0.0619 after correction. The Ratio of minimum to maximum transmission is 0.8978. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16062
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.527
_diffrn_reflns_theta_min         2.286
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2349
_reflns_number_total             3806
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.063
_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)+(0.0398P)²+0.5781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1285
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C2(H2), C5(H5), C6(H6), C17(H17), C19(H19), C22(H22),
 C13(H13), C11(H11)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.08677(6) 1.22750(13) 0.53578(3) 0.0432(3) Uani 1 1 d . . . . .
O2 O 0.47593(15) 0.3316(3) 0.69705(7) 0.0270(5) Uani 1 1 d . . . . .
O3 O 0.48792(16) 0.9318(3) 0.55881(7) 0.0344(5) Uani 1 1 d . . . . .
O1 O 0.02988(15) 0.3239(3) 0.82553(7) 0.0351(5) Uani 1 1 d . . . . .
O4 O 0.58387(17) 0.7382(4) 0.50030(7) 0.0386(5) Uani 1 1 d . . . . .
H4 H 0.563966 0.848810 0.482188 0.058 Uiso 1 1 calc GR . . . .
C8 C 0.3855(2) 0.4763(5) 0.68941(10) 0.0249(6) Uani 1 1 d . . . . .
C14 C 0.5703(2) 0.5754(5) 0.58101(10) 0.0253(6) Uani 1 1 d . . . . .
C4 C 0.3162(2) 0.7518(5) 0.62103(10) 0.0227(6) Uani 1 1 d . . . . .
C10 C 0.5463(2) 0.3589(5) 0.65663(10) 0.0248(6) Uani 1 1 d . . . . .
C9 C 0.5048(2) 0.5279(5) 0.62432(10) 0.0251(6) Uani 1 1 d . . . . .
C18 C 0.2958(2) 0.4437(5) 0.72626(10) 0.0244(6) Uani 1 1 d . . . . .
C7 C 0.3987(2) 0.5995(5) 0.64596(10) 0.0242(6) Uani 1 1 d . . . . .
C20 C 0.3002(2) 0.2605(5) 0.75985(10) 0.0281(7) Uani 1 1 d . . . . .
H20 H 0.364210 0.164113 0.759823 0.034 Uiso 1 1 calc R . . . .
C3 C 0.2703(2) 0.6861(5) 0.57551(10) 0.0269(7) Uani 1 1 d . . . . .
H3 H 0.288615 0.540740 0.561740 0.032 Uiso 1 1 calc R . . . .
C2 C 0.1979(2) 0.8299(5) 0.54977(11) 0.0308(7) Uani 1 1 d . . . . .
H2 H 0.166190 0.783292 0.518664 0.037 Uiso 1 1 calc R . . . .
C5 C 0.2871(2) 0.9637(5) 0.64073(10) 0.0286(7) Uani 1 1 d . . . . .
H5 H 0.317332 1.009419 0.672189 0.034 Uiso 1 1 calc R . . . .
C21 C 0.1203(2) 0.3523(5) 0.79417(10) 0.0277(7) Uani 1 1 d . . . . .
C15 C 0.5426(2) 0.7642(5) 0.54581(10) 0.0264(6) Uani 1 1 d . . . . .
C6 C 0.2151(2) 1.1102(5) 0.61559(11) 0.0310(7) Uani 1 1 d . . . . .
H6 H 0.195474 1.254580 0.629504 0.037 Uiso 1 1 calc R . . . .
C17 C 0.2000(2) 0.5834(5) 0.72833(10) 0.0316(7) Uani 1 1 d . . . . .
H17 H 0.193871 0.710985 0.706346 0.038 Uiso 1 1 calc R . . . .
C1 C 0.1724(2) 1.0412(5) 0.56978(11) 0.0296(7) Uani 1 1 d . . . . .
C19 C 0.2144(2) 0.2141(5) 0.79334(10) 0.0311(7) Uani 1 1 d . . . . .
H19 H 0.220167 0.087569 0.815657 0.037 Uiso 1 1 calc R . . . .
C22 C 0.1142(2) 0.5380(5) 0.76194(11) 0.0333(7) Uani 1 1 d . . . . .
H22 H 0.050668 0.635608 0.762827 0.040 Uiso 1 1 calc R . . . .
C13 C 0.6659(2) 0.4446(5) 0.57234(11) 0.0315(7) Uani 1 1 d . . . . .
H13 H 0.708852 0.474741 0.543129 0.038 Uiso 1 1 calc R . . . .
C11 C 0.6408(2) 0.2311(5) 0.64869(10) 0.0305(7) Uani 1 1 d . . . . .
H11 H 0.664329 0.118951 0.672319 0.037 Uiso 1 1 calc R . . . .
C12 C 0.7012(2) 0.2707(5) 0.60493(10) 0.0319(7) Uani 1 1 d . . . . .
C23 C 0.0305(3) 0.1298(6) 0.85841(12) 0.0440(9) Uani 1 1 d . . . . .
H23A H 0.035671 -0.011131 0.838529 0.066 Uiso 1 1 calc GR . . . .
H23B H -0.038546 0.127844 0.878094 0.066 Uiso 1 1 calc GR . . . .
H23C H 0.094973 0.139850 0.881106 0.066 Uiso 1 1 calc GR . . . .
C16 C 0.8028(3) 0.1293(6) 0.59229(12) 0.0511(10) Uani 1 1 d . . . . .
H16A H 0.779961 -0.005801 0.572971 0.077 Uiso 1 1 calc GR . . . .
H16B H 0.839785 0.080290 0.623360 0.077 Uiso 1 1 calc GR . . . .
H16C H 0.854760 0.221637 0.572333 0.077 Uiso 1 1 calc GR . . . .


_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
Cl1 C1 1.745(3) . ?
O2 C8 1.386(3) . ?
O2 C10 1.377(3) . ?
O3 C15 1.227(3) . ?
O1 C21 1.379(3) . ?
O1 C23 1.432(3) . ?
O4 H4 0.8400 . ?
O4 C15 1.319(3) . ?
C8 C18 1.469(4) . ?
C8 C7 1.372(4) . ?
C14 C9 1.423(4) . ?
C14 C15 1.483(4) . ?
C14 C13 1.395(4) . ?
C4 C7 1.484(4) . ?
C4 C3 1.384(4) . ?
C4 C5 1.388(4) . ?
C10 C9 1.399(4) . ?
C10 C11 1.371(4) . ?
C9 C7 1.456(4) . ?
C18 C20 1.395(4) . ?
C18 C17 1.407(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.389(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C21 C19 1.384(4) . ?
C21 C22 1.384(4) . ?
C6 H6 0.9500 . ?
C6 C1 1.381(4) . ?
C17 H17 0.9500 . ?
C17 C22 1.389(4) . ?
C19 H19 0.9500 . ?
C22 H22 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.400(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(4) . ?
C12 C16 1.507(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C10 O2 C8 107.0(2) . . ?
C21 O1 C23 117.6(2) . . ?
C15 O4 H4 109.5 . . ?
O2 C8 C18 113.2(2) . . ?
C7 C8 O2 110.6(2) . . ?
C7 C8 C18 135.9(2) . . ?
C9 C14 C15 122.3(2) . . ?
C13 C14 C9 118.8(2) . . ?
C13 C14 C15 118.9(3) . . ?
C3 C4 C7 119.3(2) . . ?
C3 C4 C5 118.6(2) . . ?
C5 C4 C7 122.1(2) . . ?
O2 C10 C9 110.2(2) . . ?
C11 C10 O2 124.3(2) . . ?
C11 C10 C9 125.4(3) . . ?
C14 C9 C7 138.3(2) . . ?
C10 C9 C14 116.1(2) . . ?
C10 C9 C7 105.5(2) . . ?
C20 C18 C8 120.1(2) . . ?
C20 C18 C17 116.6(3) . . ?
C17 C18 C8 123.2(2) . . ?
C8 C7 C4 127.8(3) . . ?
C8 C7 C9 106.6(2) . . ?
C9 C7 C4 125.0(2) . . ?
C18 C20 H20 118.8 . . ?
C19 C20 C18 122.3(3) . . ?
C19 C20 H20 118.8 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C3 C2 H2 120.4 . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.4 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
O1 C21 C19 125.3(3) . . ?
O1 C21 C22 115.5(3) . . ?
C22 C21 C19 119.2(3) . . ?
O3 C15 O4 123.5(2) . . ?
O3 C15 C14 122.1(3) . . ?
O4 C15 C14 114.3(3) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C18 C17 H17 119.4 . . ?
C22 C17 C18 121.2(3) . . ?
C22 C17 H17 119.4 . . ?
C2 C1 Cl1 119.1(2) . . ?
C2 C1 C6 121.4(3) . . ?
C6 C1 Cl1 119.5(2) . . ?
C20 C19 H19 120.0 . . ?
C21 C19 C20 119.9(3) . . ?
C21 C19 H19 120.0 . . ?
C21 C22 C17 120.7(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C14 C13 H13 118.7 . . ?
C14 C13 C12 122.7(3) . . ?
C12 C13 H13 118.7 . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 118.0(3) . . ?
C12 C11 H11 121.0 . . ?
C13 C12 C16 120.0(3) . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 C16 121.1(3) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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_oy_0m
_database_code_depnum_ccdc_archive 'CCDC 2086129'
loop_
_audit_author_name
_audit_author_address
'Liyao Zheng'
;Guangzhou University
China
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 O3'
_chemical_formula_sum            'C21 H14 O3'
_chemical_formula_weight         314.32
_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 0.0033 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.1028(3)
_cell_length_b                   13.2506(5)
_cell_length_c                   18.8577(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.524(2)
_cell_angle_gamma                90
_cell_volume                     1520.19(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3334
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.264
_cell_measurement_theta_min      3.075
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1126 before and 0.0695 after correction. The Ratio of minimum to maximum transmission is 0.9259. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17213
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_min         2.167
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2099
_reflns_number_total             3121
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.041
_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)+(0.0430P)²+0.4135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1157
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C17(H17), C20(H20), C19(H19), C14(H14), C2(H2), C10(H10), C5(H5),
 C13(H13), C11(H11), C4(H4), C3(H3), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3 O 0.1779(2) 0.45848(9) 0.18673(7) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.2431(2) 0.43845(10) 0.07451(7) 0.0365(4) Uani 1 1 d . . . . .
O1 O 0.9435(2) 0.64766(11) 0.05180(7) 0.0374(4) Uani 1 1 d . . . . .
H1 H 0.901821 0.617847 0.013795 0.056 Uiso 1 1 calc GR . . . .
C21 C 0.5027(3) 0.60407(13) 0.20791(9) 0.0238(4) Uani 1 1 d . . . . .
C1 C 0.3680(3) 0.64448(13) 0.32942(10) 0.0248(4) Uani 1 1 d . . . . .
C7 C 0.3552(3) 0.58288(13) 0.26279(9) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.2047(3) 0.50869(13) 0.25203(10) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.1934(3) 0.70723(14) 0.34287(10) 0.0292(5) Uani 1 1 d . . . . .
H6 H 0.068256 0.710245 0.309625 0.035 Uiso 1 1 calc R . . . .
C17 C 0.6244(3) 0.56338(13) 0.09079(10) 0.0277(4) Uani 1 1 d . . . . .
H17 H 0.606099 0.525435 0.047994 0.033 Uiso 1 1 calc R . . . .
C15 C 0.2968(3) 0.48010(14) 0.13042(10) 0.0274(4) Uani 1 1 d . . . . .
C16 C 0.4790(3) 0.55024(13) 0.14350(10) 0.0254(4) Uani 1 1 d . . . . .
C20 C 0.6750(3) 0.67486(13) 0.21569(10) 0.0258(4) Uani 1 1 d . . . . .
H20 H 0.692965 0.714304 0.257820 0.031 Uiso 1 1 calc R . . . .
C19 C 0.8178(3) 0.68808(14) 0.16368(10) 0.0280(4) Uani 1 1 d . . . . .
H19 H 0.933122 0.736093 0.170432 0.034 Uiso 1 1 calc R . . . .
C9 C 0.0505(3) 0.46565(13) 0.30022(10) 0.0260(4) Uani 1 1 d . . . . .
C18 C 0.7950(3) 0.63159(14) 0.10088(10) 0.0279(4) Uani 1 1 d . . . . .
C14 C -0.1487(3) 0.42533(13) 0.27171(11) 0.0292(5) Uani 1 1 d . . . . .
H14 H -0.184473 0.427519 0.221787 0.035 Uiso 1 1 calc R . . . .
C2 C 0.5524(3) 0.64267(14) 0.37780(10) 0.0303(5) Uani 1 1 d . . . . .
H2 H 0.674796 0.601536 0.368924 0.036 Uiso 1 1 calc R . . . .
C10 C 0.0999(3) 0.45974(14) 0.37400(11) 0.0322(5) Uani 1 1 d . . . . .
H10 H 0.235339 0.485871 0.394558 0.039 Uiso 1 1 calc R . . . .
C5 C 0.1992(3) 0.76520(15) 0.40382(11) 0.0360(5) Uani 1 1 d . . . . .
H5 H 0.078263 0.807391 0.412434 0.043 Uiso 1 1 calc R . . . .
C13 C -0.2946(3) 0.38224(14) 0.31543(11) 0.0344(5) Uani 1 1 d . . . . .
H13 H -0.429849 0.355380 0.295317 0.041 Uiso 1 1 calc R . . . .
C11 C -0.0471(4) 0.41614(14) 0.41703(11) 0.0364(5) Uani 1 1 d . . . . .
H11 H -0.011912 0.412373 0.466941 0.044 Uiso 1 1 calc R . . . .
C4 C 0.3808(4) 0.76180(15) 0.45223(11) 0.0373(5) Uani 1 1 d . . . . .
H4 H 0.384566 0.801078 0.494451 0.045 Uiso 1 1 calc R . . . .
C3 C 0.5573(3) 0.70111(15) 0.43910(11) 0.0358(5) Uani 1 1 d . . . . .
H3 H 0.682825 0.699321 0.472226 0.043 Uiso 1 1 calc R . . . .
C12 C -0.2451(4) 0.37799(15) 0.38790(12) 0.0382(5) Uani 1 1 d . . . . .
H12 H -0.346543 0.348984 0.417744 0.046 Uiso 1 1 calc R . . . .


_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
O3 C8 1.398(2) . ?
O3 C15 1.363(2) . ?
O2 C15 1.212(2) . ?
O1 H1 0.8400 . ?
O1 C18 1.362(2) . ?
C21 C7 1.452(3) . ?
C21 C16 1.406(2) . ?
C21 C20 1.408(2) . ?
C1 C7 1.495(2) . ?
C1 C6 1.391(3) . ?
C1 C2 1.392(3) . ?
C7 C8 1.350(2) . ?
C8 C9 1.473(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.394(3) . ?
C17 C18 1.380(3) . ?
C15 C16 1.455(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.373(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.399(3) . ?
C9 C14 1.396(3) . ?
C9 C10 1.402(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C12 H12 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
C15 O3 C8 123.64(14) . . ?
C18 O1 H1 109.5 . . ?
C16 C21 C7 119.38(16) . . ?
C16 C21 C20 116.92(17) . . ?
C20 C21 C7 123.69(16) . . ?
C6 C1 C7 119.30(16) . . ?
C6 C1 C2 118.84(17) . . ?
C2 C1 C7 121.84(16) . . ?
C21 C7 C1 119.94(16) . . ?
C8 C7 C21 119.12(17) . . ?
C8 C7 C1 120.93(17) . . ?
O3 C8 C9 108.86(15) . . ?
C7 C8 O3 120.65(17) . . ?
C7 C8 C9 130.48(17) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.99(18) . . ?
C5 C6 H6 119.5 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 119.93(17) . . ?
O3 C15 C16 116.67(16) . . ?
O2 C15 O3 117.25(16) . . ?
O2 C15 C16 126.07(18) . . ?
C21 C16 C15 119.68(17) . . ?
C17 C16 C21 121.65(17) . . ?
C17 C16 C15 118.66(17) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 C21 121.41(17) . . ?
C19 C20 H20 119.3 . . ?
C20 C19 H19 119.7 . . ?
C20 C19 C18 120.69(17) . . ?
C18 C19 H19 119.7 . . ?
C14 C9 C8 119.32(17) . . ?
C14 C9 C10 118.23(18) . . ?
C10 C9 C8 122.39(17) . . ?
O1 C18 C17 122.93(17) . . ?
O1 C18 C19 117.70(17) . . ?
C17 C18 C19 119.36(18) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.69(19) . . ?
C13 C14 H14 119.7 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.91(18) . . ?
C3 C2 H2 120.0 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.45(19) . . ?
C11 C10 H10 119.8 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.94(19) . . ?
C4 C5 H5 120.0 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.47(19) . . ?
C12 C13 H13 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.81(19) . . ?
C3 C4 H4 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.50(19) . . ?
C4 C3 H3 119.7 . . ?
C13 C12 C11 119.70(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 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_oy742
_database_code_depnum_ccdc_archive 'CCDC 2086132'
loop_
_audit_author_name
_audit_author_address
'Liyao Zheng'
;Guangzhou University
China
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 O5'
_chemical_formula_sum            'C25 H20 O5'
_chemical_formula_weight         400.41
_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 0.0033 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1604(17)
_cell_length_b                   26.865(4)
_cell_length_c                   7.3080(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.982(5)
_cell_angle_gamma                90
_cell_volume                     1886.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4923
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.090
_cell_measurement_theta_min      2.251
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1312 before and 0.0760 after correction. The Ratio of minimum to maximum transmission is 0.7188. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18045
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.120
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2517
_reflns_number_total             3807
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.072
_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)+(0.0679P)²+1.3451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C22(H22), C4(H4), C15(H15), C7(H7), C3(H3), C6(H6), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O4 O 0.5818(2) 0.58800(6) 0.2663(3) 0.0361(5) Uani 1 1 d . . . . .
O2 O 0.5964(2) 0.32956(7) 0.4199(3) 0.0375(5) Uani 1 1 d . . . . .
O3 O 0.1419(2) 0.50788(7) -0.0466(3) 0.0396(5) Uani 1 1 d . . . . .
O5 O 0.7854(2) 0.53439(7) 0.4780(3) 0.0379(5) Uani 1 1 d . . . . .
O1 O -0.0405(2) 0.26954(7) 0.0508(3) 0.0458(6) Uani 1 1 d . . . . .
C19 C 0.4690(3) 0.45811(9) 0.2574(4) 0.0299(6) Uani 1 1 d . . . . .
C16 C 0.7673(3) 0.44722(9) 0.4815(4) 0.0278(6) Uani 1 1 d . . . . .
C18 C 0.5594(3) 0.50090(9) 0.3037(4) 0.0288(6) Uani 1 1 d . . . . .
C9 C 0.5292(3) 0.40984(9) 0.3355(4) 0.0299(6) Uani 1 1 d . . . . .
C21 C 0.2777(3) 0.50819(10) 0.0676(4) 0.0307(6) Uani 1 1 d . . . . .
C10 C 0.6737(3) 0.40809(9) 0.4334(4) 0.0307(6) Uani 1 1 d . . . . .
C17 C 0.7095(3) 0.49777(9) 0.4246(4) 0.0286(6) Uani 1 1 d . . . . .
C23 C 0.4984(3) 0.54694(9) 0.2257(4) 0.0299(6) Uani 1 1 d . . . . .
C20 C 0.3320(3) 0.46228(10) 0.1400(4) 0.0306(6) Uani 1 1 d . . . . .
H20 H 0.274795 0.433478 0.108752 0.037 Uiso 1 1 calc R . . . .
C22 C 0.3596(3) 0.55070(10) 0.1119(4) 0.0328(7) Uani 1 1 d . . . . .
H22 H 0.320907 0.582209 0.064633 0.039 Uiso 1 1 calc R . . . .
C4 C 0.2349(3) 0.35780(10) 0.3071(4) 0.0338(7) Uani 1 1 d . . . . .
H4 H 0.247189 0.387625 0.380660 0.041 Uiso 1 1 calc R . . . .
C15 C 0.9056(3) 0.43552(10) 0.5810(4) 0.0317(7) Uani 1 1 d . . . . .
H15 H 0.972740 0.461430 0.616515 0.038 Uiso 1 1 calc R . . . .
C8 C 0.4834(3) 0.36152(10) 0.3329(4) 0.0340(7) Uani 1 1 d . . . . .
C5 C 0.3484(3) 0.33687(10) 0.2681(4) 0.0321(7) Uani 1 1 d . . . . .
C2 C 0.0857(3) 0.29272(10) 0.1312(4) 0.0354(7) Uani 1 1 d . . . . .
C11 C 0.7134(3) 0.35938(10) 0.4835(4) 0.0343(7) Uani 1 1 d . . . . .
C7 C 0.1990(3) 0.27008(10) 0.0981(4) 0.0378(7) Uani 1 1 d . . . . .
H7 H 0.186914 0.239556 0.028921 0.045 Uiso 1 1 calc R . . . .
C3 C 0.1048(3) 0.33604(10) 0.2410(4) 0.0339(7) Uani 1 1 d . . . . .
H3 H 0.028829 0.350566 0.270413 0.041 Uiso 1 1 calc R . . . .
C13 C 0.9478(3) 0.38592(10) 0.6300(4) 0.0332(7) Uani 1 1 d . . . . .
C6 C 0.3280(3) 0.29171(10) 0.1650(4) 0.0381(7) Uani 1 1 d . . . . .
H6 H 0.404733 0.276022 0.141375 0.046 Uiso 1 1 calc R . . . .
C14 C 1.0971(3) 0.37411(10) 0.7364(4) 0.0385(7) Uani 1 1 d . . . . .
H14A H 1.156810 0.398885 0.704158 0.058 Uiso 1 1 calc GR . . . .
H14B H 1.119198 0.340941 0.698791 0.058 Uiso 1 1 calc GR . . . .
H14C H 1.112965 0.374756 0.876068 0.058 Uiso 1 1 calc GR . . . .
C25 C 0.0743(3) 0.55469(10) -0.1062(4) 0.0368(7) Uani 1 1 d . . . . .
H25A H -0.021933 0.548955 -0.189018 0.055 Uiso 1 1 calc GR . . . .
H25B H 0.124019 0.573353 -0.178604 0.055 Uiso 1 1 calc GR . . . .
H25C H 0.074436 0.573816 0.008022 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.8495(3) 0.34679(10) 0.5814(4) 0.0376(7) Uani 1 1 d . . . . .
H12 H 0.876219 0.313247 0.614795 0.045 Uiso 1 1 calc R . . . .
C24 C 0.5241(3) 0.63496(10) 0.1888(4) 0.0404(7) Uani 1 1 d . . . . .
H24A H 0.487110 0.632794 0.047327 0.061 Uiso 1 1 calc GR . . . .
H24B H 0.596715 0.660538 0.226463 0.061 Uiso 1 1 calc GR . . . .
H24C H 0.448848 0.643753 0.239310 0.061 Uiso 1 1 calc GR . . . .
C1 C -0.1607(4) 0.29290(12) 0.0712(6) 0.0554(9) Uani 1 1 d . . . . .
H1A H -0.243432 0.273194 0.003608 0.083 Uiso 1 1 calc GR . . . .
H1B H -0.170296 0.326396 0.015272 0.083 Uiso 1 1 calc GR . . . .
H1C H -0.151202 0.295194 0.208750 0.083 Uiso 1 1 calc GR . . . .


_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
O4 C23 1.363(3) . ?
O4 C24 1.428(3) . ?
O2 C8 1.409(3) . ?
O2 C11 1.383(3) . ?
O3 C21 1.361(3) . ?
O3 C25 1.431(3) . ?
O5 C17 1.233(3) . ?
O1 C2 1.374(3) . ?
O1 C1 1.423(4) . ?
C19 C18 1.442(4) . ?
C19 C9 1.467(4) . ?
C19 C20 1.382(4) . ?
C16 C10 1.384(4) . ?
C16 C17 1.484(3) . ?
C16 C15 1.392(4) . ?
C18 C17 1.495(4) . ?
C18 C23 1.417(4) . ?
C9 C10 1.409(4) . ?
C9 C8 1.377(4) . ?
C21 C20 1.384(4) . ?
C21 C22 1.388(4) . ?
C10 C11 1.383(4) . ?
C23 C22 1.389(4) . ?
C20 H20 0.9500 . ?
C22 H22 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.394(4) . ?
C4 C3 1.380(4) . ?
C15 H15 0.9500 . ?
C15 C13 1.410(4) . ?
C8 C5 1.457(4) . ?
C5 C6 1.408(4) . ?
C2 C7 1.391(4) . ?
C2 C3 1.391(4) . ?
C11 C12 1.376(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.370(4) . ?
C3 H3 0.9500 . ?
C13 C14 1.496(4) . ?
C13 C12 1.413(4) . ?
C6 H6 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C12 H12 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C23 O4 C24 118.8(2) . . ?
C11 O2 C8 106.5(2) . . ?
C21 O3 C25 118.2(2) . . ?
C2 O1 C1 118.0(2) . . ?
C18 C19 C9 117.4(3) . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 C9 121.4(2) . . ?
C10 C16 C17 116.6(2) . . ?
C10 C16 C15 117.0(2) . . ?
C15 C16 C17 126.4(2) . . ?
C19 C18 C17 122.9(2) . . ?
C23 C18 C19 116.1(3) . . ?
C23 C18 C17 121.0(2) . . ?
C10 C9 C19 117.4(2) . . ?
C8 C9 C19 137.0(3) . . ?
C8 C9 C10 105.5(2) . . ?
O3 C21 C20 115.3(2) . . ?
O3 C21 C22 124.0(2) . . ?
C20 C21 C22 120.6(3) . . ?
C16 C10 C9 128.3(2) . . ?
C11 C10 C16 122.3(3) . . ?
C11 C10 C9 109.4(2) . . ?
O5 C17 C16 119.4(2) . . ?
O5 C17 C18 123.7(2) . . ?
C16 C17 C18 116.8(2) . . ?
O4 C23 C18 117.3(3) . . ?
O4 C23 C22 120.6(2) . . ?
C22 C23 C18 122.0(2) . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C21 C22 C23 119.7(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C16 C15 C13 121.2(3) . . ?
C13 C15 H15 119.4 . . ?
O2 C8 C5 114.4(2) . . ?
C9 C8 O2 110.3(2) . . ?
C9 C8 C5 135.3(3) . . ?
C4 C5 C8 120.3(2) . . ?
C4 C5 C6 118.0(3) . . ?
C6 C5 C8 121.6(3) . . ?
O1 C2 C7 116.0(2) . . ?
O1 C2 C3 124.2(3) . . ?
C3 C2 C7 119.9(3) . . ?
O2 C11 C10 108.3(3) . . ?
C12 C11 O2 129.9(2) . . ?
C12 C11 C10 121.8(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C15 C13 C14 120.4(3) . . ?
C15 C13 C12 120.5(3) . . ?
C12 C13 C14 119.1(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C11 C12 C13 117.1(3) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 H12 121.4 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
