# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_2023-11
_database_code_depnum_ccdc_archive 'CCDC 2404519'
loop_
_audit_author_name
_audit_author_address
'HUI YAO'
;China Three Gorges University
China
;
_audit_update_record             
;
2024-11-22 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-05-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H32 O4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0492 0.0322 '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                   8.6971(6)
_cell_length_b                   5.8730(4)
_cell_length_c                   12.5155(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.239(7)
_cell_angle_gamma                90
_cell_volume                     637.52(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4164
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.9450
_cell_measurement_theta_min      6.0060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1154
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4254
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.296
_diffrn_reflns_theta_min         5.099
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  31.00   0.50    0.50    --    0.00 -82.00 -90.00  116
  2  ω      2.00  31.00   0.50    0.50    --    0.00 -82.00   0.00   58
  3  ω    -45.00   0.00   0.50    0.50    --    0.00 -77.00  60.00   90
  4  ω     80.00 152.00   0.50    0.50    --   95.80  30.00  90.00  144
  5  ω     83.00 126.00   0.50    0.50    --   95.80 -82.00  30.00   86
  6  ω     25.00 105.00   0.50    0.50    --   95.80 -30.00-120.00  160
  7  ω     73.00 160.00   0.50    0.50    --   95.80  61.00-180.00  174
  8  ω      7.00  48.00   0.50    0.50    --   95.80 -82.00  30.00   82
  9  ω     79.00 145.00   0.50    0.50    --   95.80  30.00-180.00  132
 10  ω    155.00 180.00   0.50    0.50    --   95.80  82.00-120.00   50
 11  ω     90.00 145.00   0.50    0.50    --   95.80  30.00 120.00  110
 12  ω    160.00 185.00   0.50    0.50    --   95.80  30.00  30.00   50
 13  ω    -26.00  24.00   0.50    0.50    --    0.00 -82.00 150.00  100
 14  ω    -25.00   1.00   0.50    0.50    --    0.00 -82.00-180.00   52
 15  ω    -27.00  -2.00   0.50    0.50    --    0.00 -82.00 -30.00   50
 16  ω     10.00  53.00   0.50    0.50    --   95.80 -15.00  60.00   86
 17  ω    136.00 172.00   0.50    0.50    --   95.80  82.00 -30.00   72
 18  ω     72.00  98.00   0.50    0.50    --   95.80  61.00 120.00   52
 19  ω     87.00 113.00   0.50    0.50    --   95.80  82.00 -30.00   52
 20  ω     81.00 107.00   0.50    0.50    --   95.80 -61.00  60.00   52
 21  ω     94.00 129.00   0.50    0.50    --   95.80  45.00-150.00   70
 22  ω    146.00 182.00   0.50    0.50    --   95.80  45.00-150.00   72
 23  ω     27.00  53.00   0.50    0.50    --   95.80 -77.00 -60.00   52
 24  ω     82.00 120.00   0.50    0.50    --   95.80 -77.00 -60.00   76
 25  ω     39.00  65.00   0.50    0.50    --   95.80 -61.00  60.00   52
 26  ω     73.00  86.50   0.50    0.50    --   95.80  61.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127613000
_diffrn_orient_matrix_UB_12      0.1123121000
_diffrn_orient_matrix_UB_13      -0.1101957000
_diffrn_orient_matrix_UB_21      0.1716480000
_diffrn_orient_matrix_UB_22      -0.0661579000
_diffrn_orient_matrix_UB_23      0.0035794000
_diffrn_orient_matrix_UB_31      -0.0437238000
_diffrn_orient_matrix_UB_32      -0.2276666000
_diffrn_orient_matrix_UB_33      -0.0555230000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.597
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                2161
_reflns_number_total             2230
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.056(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.025
_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)+(0.1389P)²+0.0169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1576
_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 Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.d 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 0.66204(18) 0.4175(3) 0.15985(12) 0.0249(5) Uani 1 1 d . . . . .
O2 O 0.5823(2) 0.7461(4) -0.01185(13) 0.0366(6) Uani 1 1 d . . . . .
H2 H 0.509067 0.831896 -0.033187 0.055 Uiso 1 1 calc R U . . .
C1 C 0.6577(3) 0.4176(4) 0.35435(18) 0.0239(6) Uani 1 1 d . . . . .
C2 C 0.6553(3) 0.5744(4) 0.43540(18) 0.0242(5) Uani 1 1 d . . . . .
H2A H 0.597179 0.710350 0.424307 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7390(3) 0.5359(4) 0.53615(19) 0.0249(6) Uani 1 1 d . . . . .
C4 C 0.7386(3) 0.6956(5) 0.6211(2) 0.0299(6) Uani 1 1 d . . . . .
H4 H 0.681269 0.832696 0.611359 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8201(3) 0.6542(6) 0.7170(2) 0.0339(7) Uani 1 1 d . . . . .
H5 H 0.818862 0.762573 0.773260 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9056(3) 0.4521(6) 0.7326(2) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.961179 0.424755 0.799544 0.040 Uiso 1 1 calc R U . . .
C7 C 0.9096(3) 0.2943(5) 0.6522(2) 0.0301(6) Uani 1 1 d . . . . .
H7 H 0.968452 0.159063 0.663582 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8259(3) 0.3324(5) 0.55145(19) 0.0256(6) Uani 1 1 d . . . . .
C9 C 0.8277(3) 0.1747(5) 0.4662(2) 0.0291(6) Uani 1 1 d . . . . .
H9 H 0.886666 0.039097 0.475472 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7454(3) 0.2148(5) 0.3705(2) 0.0291(6) Uani 1 1 d . . . . .
H10 H 0.747064 0.106136 0.314350 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5645(3) 0.4453(4) 0.24699(19) 0.0248(6) Uani 1 1 d . . . . .
H11 H 0.489220 0.316445 0.241543 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4716(3) 0.6590(5) 0.23515(18) 0.0278(6) Uani 1 1 d . . . . .
H12 H 0.389139 0.680401 0.279845 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4994(3) 0.8194(5) 0.16506(19) 0.0296(6) Uani 1 1 d . . . . .
H13 H 0.432821 0.947653 0.158062 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6339(3) 0.8045(5) 0.09590(18) 0.0285(6) Uani 1 1 d . . . . .
H14 H 0.688388 0.954413 0.096398 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7455(3) 0.6208(5) 0.13859(18) 0.0264(6) Uani 1 1 d . . . . .
H15 H 0.799366 0.675456 0.207169 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8656(3) 0.5550(6) 0.0626(2) 0.0387(7) Uani 1 1 d . . . . .
H16A H 0.940643 0.451233 0.098950 0.058 Uiso 1 1 calc R U . . .
H16B H 0.918684 0.692058 0.039963 0.058 Uiso 1 1 calc R U . . .
H16C H 0.815284 0.479093 -0.000399 0.058 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
O1 C11 1.439(3) . ?
O1 C15 1.432(3) . ?
O2 H2 0.8400 . ?
O2 C14 1.431(3) . ?
C1 C2 1.371(3) . ?
C1 C10 1.420(4) . ?
C1 C11 1.526(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.427(3) . ?
C3 C4 1.418(4) . ?
C3 C8 1.420(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.406(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.370(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.426(3) . ?
C8 C9 1.413(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.370(4) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.494(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.322(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.508(4) . ?
C14 H14 1.0000 . ?
C14 C15 1.521(4) . ?
C15 H15 1.0000 . ?
C15 C16 1.514(3) . ?
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
C15 O1 C11 112.40(18) . . ?
C14 O2 H2 109.5 . . ?
C2 C1 C10 119.7(2) . . ?
C2 C1 C11 122.9(2) . . ?
C10 C1 C11 117.3(2) . . ?
C1 C2 H2A 119.6 . . ?
C1 C2 C3 120.9(2) . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 C8 119.1(2) . . ?
C8 C3 C2 119.0(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 118.9(2) . . ?
C9 C8 C3 119.0(2) . . ?
C9 C8 C7 122.1(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C1 C10 H10 119.7 . . ?
C9 C10 C1 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
O1 C11 C1 110.54(17) . . ?
O1 C11 H11 106.4 . . ?
O1 C11 C12 111.4(2) . . ?
C1 C11 H11 106.4 . . ?
C12 C11 C1 115.2(2) . . ?
C12 C11 H11 106.4 . . ?
C11 C12 H12 118.6 . . ?
C13 C12 C11 122.7(2) . . ?
C13 C12 H12 118.6 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
O2 C14 C13 110.6(2) . . ?
O2 C14 H14 109.4 . . ?
O2 C14 C15 108.0(2) . . ?
C13 C14 H14 109.4 . . ?
C13 C14 C15 110.0(2) . . ?
C15 C14 H14 109.4 . . ?
O1 C15 C14 109.72(19) . . ?
O1 C15 H15 108.7 . . ?
O1 C15 C16 106.7(2) . . ?
C14 C15 H15 108.7 . . ?
C16 C15 C14 114.3(2) . . ?
C16 C15 H15 108.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C13 -12.1(3) . . . . ?
O2 C14 C15 O1 -73.3(2) . . . . ?
O2 C14 C15 C16 46.4(3) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C1 C2 C3 C8 0.3(3) . . . . ?
C1 C11 C12 C13 114.8(3) . . . . ?
C2 C1 C10 C9 -0.1(3) . . . . ?
C2 C1 C11 O1 128.4(2) . . . . ?
C2 C1 C11 C12 1.1(3) . . . . ?
C2 C3 C4 C5 -180.0(2) . . . . ?
C2 C3 C8 C7 179.9(2) . . . . ?
C2 C3 C8 C9 0.4(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C8 C9 C10 -0.9(4) . . . . ?
C4 C3 C8 C7 0.3(3) . . . . ?
C4 C3 C8 C9 -179.2(2) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C3 0.1(4) . . . . ?
C6 C7 C8 C9 179.6(2) . . . . ?
C7 C8 C9 C10 179.6(2) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C8 C9 C10 C1 0.7(4) . . . . ?
C10 C1 C2 C3 -0.4(3) . . . . ?
C10 C1 C11 O1 -54.0(3) . . . . ?
C10 C1 C11 C12 178.7(2) . . . . ?
C11 O1 C15 C14 -67.1(2) . . . . ?
C11 O1 C15 C16 168.59(18) . . . . ?
C11 C1 C2 C3 177.1(2) . . . . ?
C11 C1 C10 C9 -177.7(2) . . . . ?
C11 C12 C13 C14 -3.7(4) . . . . ?
C12 C13 C14 O2 105.2(3) . . . . ?
C12 C13 C14 C15 -13.9(3) . . . . ?
C13 C14 C15 O1 47.4(3) . . . . ?
C13 C14 C15 C16 167.2(2) . . . . ?
C15 O1 C11 C1 -81.7(2) . . . . ?
C15 O1 C11 C12 47.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.291
_oxdiff_exptl_absorpt_empirical_full_min 0.510
####################################################################### 
# 
# 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_2023-77
_database_code_depnum_ccdc_archive 'CCDC 2404613'
loop_
_audit_author_name
_audit_author_address
'HUI YAO'
;China Three Gorges University
China
;
_audit_update_record             
;
2024-11-22 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_audit_creation_date             2024-11-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 O2'
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26
_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 0.0181 0.0091 '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 0.0492 0.0322 '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                   10.87836(11)
_cell_length_b                   4.91995(6)
_cell_length_c                   21.8073(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.9801(9)
_cell_angle_gamma                90
_cell_volume                     1166.45(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6493
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.7080
_cell_measurement_theta_min      2.0130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7566
_diffrn_reflns_point_group_measured_fraction_full 0.730
_diffrn_reflns_point_group_measured_fraction_max 0.682
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.161
_diffrn_reflns_theta_min         2.027
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  68.00   0.50    0.70    --  106.53 -57.00-120.00   68
  2  ω     34.00  60.00   0.50    0.70    --  106.53 -57.00 -90.00   52
  3  ω     34.00  62.00   0.50    0.70    --  106.53 -57.00 -30.00   56
  4  ω     70.00 104.00   0.50    0.70    --  106.53 -77.00   0.00   68
  5  ω     42.00  67.00   0.50    0.70    --  106.53 -57.00  60.00   50
  6  ω     39.00  67.00   0.50    0.70    --  106.53 -57.00 150.00   56
  7  ω     38.00  67.00   0.50    0.70    --  106.53 -57.00 -60.00   58
  8  ω     37.00  68.00   0.50    0.70    --  106.53 -57.00-150.00   62
  9  ω     34.00  62.00   0.50    0.70    --  106.53 -57.00-180.00   56
 10  ω     61.00 101.00   0.50    0.70    --  106.53 -99.00-120.00   80
 11  ω    -23.00  31.00   0.50    0.50    --   48.15 -35.00 -38.00  108
 12  ω    -33.00  25.00   0.50    0.50    --  -48.15  35.00 118.00  116
 13  ω     46.00 119.00   0.50    0.50    --   48.15  35.00 118.00  146
 14  ω    119.00 145.00   0.50    0.70    --  106.53  35.00 118.00   52
 15  ω    -39.00   2.00   0.50    0.50    --  -48.15  38.00 -90.00   82
 16  ω    -63.00 -32.00   0.50    0.70    -- -104.00  57.00-120.00   62
 17  ω    -64.00 -39.00   0.50    0.70    -- -104.00  57.00 -90.00   50
 18  ω    -63.00 -33.00   0.50    0.70    -- -104.00  57.00 -30.00   60
 19  ω    -64.00 -35.00   0.50    0.70    -- -104.00  57.00  60.00   58
 20  ω    -62.00 -32.00   0.50    0.70    -- -104.00  57.00 120.00   60
 21  ω   -168.00 -93.00   0.50    0.70    -- -104.00 -19.00  30.00  150
 22  ω   -173.00-101.00   0.50    0.70    -- -104.00 -35.00 -38.00  144
 23  ω   -119.00 -37.00   0.50    0.50    --  -48.15 -35.00 -38.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1157795000
_diffrn_orient_matrix_UB_12      -0.1080346000
_diffrn_orient_matrix_UB_13      -0.0306422000
_diffrn_orient_matrix_UB_21      -0.0795421000
_diffrn_orient_matrix_UB_22      -0.0915711000
_diffrn_orient_matrix_UB_23      -0.0560714000
_diffrn_orient_matrix_UB_31      0.0186156000
_diffrn_orient_matrix_UB_32      0.2791967000
_diffrn_orient_matrix_UB_33      -0.0302661000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.275
_reflns_Friedel_fraction_full    0.384
_reflns_Friedel_fraction_max     0.334
_reflns_number_gt                3230
_reflns_number_total             3375
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_coef       0.0109(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.079
_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)+(0.0844P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1180
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C26(H26), C29(H29)
1.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C30(H30A,H30B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
  C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
 C27(H27), C28(H28)
1.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.77761(11) 0.6051(4) 0.64700(6) 0.0316(4) Uani 1 1 d . . . . .
O2 O 1.00103(14) 0.5030(4) 0.52698(6) 0.0391(4) Uani 1 1 d . . . . .
H2 H 1.005045 0.650779 0.507876 0.059 Uiso 1 1 calc R U . . .
C1 C 0.74482(15) 0.3389(5) 0.73683(8) 0.0288(5) Uani 1 1 d . . . . .
C2 C 0.65796(16) 0.1630(5) 0.75705(8) 0.0306(5) Uani 1 1 d . . . . .
H2A H 0.616575 0.046048 0.728473 0.037 Uiso 1 1 calc R U . . .
C3 C 0.62815(15) 0.1511(5) 0.82002(8) 0.0305(5) Uani 1 1 d . . . . .
C4 C 0.53891(17) -0.0306(6) 0.84118(9) 0.0381(5) Uani 1 1 d . . . . .
H4 H 0.496625 -0.147361 0.812898 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5125(2) -0.0405(6) 0.90214(10) 0.0426(6) Uani 1 1 d . . . . .
H5 H 0.452312 -0.164045 0.915992 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5745(2) 0.1322(7) 0.94407(9) 0.0456(6) Uani 1 1 d . . . . .
H6 H 0.556501 0.123330 0.986342 0.055 Uiso 1 1 calc R U . . .
C7 C 0.6601(2) 0.3121(6) 0.92499(9) 0.0447(6) Uani 1 1 d . . . . .
H7 H 0.700558 0.428083 0.954065 0.054 Uiso 1 1 calc R U . . .
C8 C 0.68989(17) 0.3289(6) 0.86184(8) 0.0332(5) Uani 1 1 d . . . . .
C9 C 0.77842(18) 0.5102(6) 0.83991(9) 0.0378(5) Uani 1 1 d . . . . .
H9 H 0.819778 0.630433 0.867775 0.045 Uiso 1 1 calc R U . . .
C10 C 0.80594(17) 0.5163(5) 0.77905(9) 0.0341(5) Uani 1 1 d . . . . .
H10 H 0.866103 0.639656 0.765138 0.041 Uiso 1 1 calc R U . . .
C11 C 0.77950(16) 0.3339(5) 0.67033(8) 0.0304(5) Uani 1 1 d . . . . .
H11 H 0.716267 0.225376 0.646667 0.036 Uiso 1 1 calc R U . . .
C12 C 0.90341(17) 0.2026(5) 0.66245(8) 0.0313(5) Uani 1 1 d . . . . .
H12 H 0.922571 0.040746 0.684526 0.038 Uiso 1 1 calc R U . . .
C13 C 0.98625(16) 0.3048(5) 0.62592(8) 0.0317(5) Uani 1 1 d . . . . .
H13 H 1.064039 0.218397 0.623611 0.038 Uiso 1 1 calc R U . . .
C14 C 0.96032(17) 0.5532(5) 0.58816(8) 0.0317(5) Uani 1 1 d . . . . .
H14 H 1.006194 0.711601 0.606374 0.038 Uiso 1 1 calc R U . . .
C15 C 0.82287(16) 0.6128(6) 0.58639(8) 0.0338(5) Uani 1 1 d . . . . .
H15A H 0.807431 0.794419 0.568167 0.041 Uiso 1 1 calc R U . . .
H15B H 0.779069 0.476171 0.560459 0.041 Uiso 1 1 calc R U . . .
O3 O 0.45328(14) 0.8807(4) 0.51554(6) 0.0431(4) Uani 1 1 d . . . . .
H3 H 0.479901 1.028480 0.502013 0.065 Uiso 1 1 calc R U . . .
O4 O 0.23347(11) 0.8052(5) 0.63666(6) 0.0441(5) Uani 1 1 d . . . . .
C16 C 0.25659(15) 0.6305(5) 0.73869(8) 0.0311(5) Uani 1 1 d . . . . .
C17 C 0.17219(16) 0.8142(6) 0.75605(9) 0.0341(5) Uani 1 1 d . . . . .
H17 H 0.136513 0.933965 0.726263 0.041 Uiso 1 1 calc R U . . .
C18 C 0.13545(16) 0.8324(6) 0.81815(9) 0.0335(5) Uani 1 1 d . . . . .
C19 C 0.04628(17) 1.0200(6) 0.83649(9) 0.0390(6) Uani 1 1 d . . . . .
H19 H 0.008560 1.138181 0.806970 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0133(2) 1.0341(7) 0.89649(10) 0.0444(6) Uani 1 1 d . . . . .
H20 H -0.047064 1.161419 0.908351 0.053 Uiso 1 1 calc R U . . .
C21 C 0.0691(2) 0.8588(7) 0.94086(9) 0.0453(6) Uani 1 1 d . . . . .
H21 H 0.046298 0.869691 0.982438 0.054 Uiso 1 1 calc R U . . .
C22 C 0.1547(2) 0.6762(6) 0.92437(9) 0.0432(6) Uani 1 1 d . . . . .
H22 H 0.191623 0.560735 0.954665 0.052 Uiso 1 1 calc R U . . .
C23 C 0.19060(17) 0.6537(6) 0.86213(9) 0.0350(5) Uani 1 1 d . . . . .
C24 C 0.27751(19) 0.4628(6) 0.84310(10) 0.0406(6) Uani 1 1 d . . . . .
H24 H 0.314672 0.342235 0.872291 0.049 Uiso 1 1 calc R U . . .
C25 C 0.30921(18) 0.4485(6) 0.78299(9) 0.0379(5) Uani 1 1 d . . . . .
H25 H 0.366887 0.315886 0.770737 0.045 Uiso 1 1 calc R U . . .
C26 C 0.29575(15) 0.6052(6) 0.67268(8) 0.0328(5) Uani 1 1 d . . . . .
H26 H 0.269110 0.422601 0.657091 0.039 Uiso 1 1 calc R U . . .
C27 C 0.43281(16) 0.6267(6) 0.66636(8) 0.0360(5) Uani 1 1 d . . . . .
H27 H 0.485468 0.530604 0.694452 0.043 Uiso 1 1 calc R U . . .
C28 C 0.48242(16) 0.7747(6) 0.62299(9) 0.0377(6) Uani 1 1 d . . . . .
H28 H 0.569471 0.787371 0.622027 0.045 Uiso 1 1 calc R U . . .
C29 C 0.40606(18) 0.9228(6) 0.57549(9) 0.0370(5) Uani 1 1 d . . . . .
H29 H 0.405975 1.121471 0.585130 0.044 Uiso 1 1 calc R U . . .
C30 C 0.27601(16) 0.8151(7) 0.57546(9) 0.0462(7) Uani 1 1 d . . . . .
H30A H 0.221463 0.934337 0.550060 0.055 Uiso 1 1 calc R U . . .
H30B H 0.273375 0.630634 0.557335 0.055 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
O1 C11 1.428(3) . ?
O1 C15 1.4267(18) . ?
O2 H2 0.8400 . ?
O2 C14 1.4417(19) . ?
C1 C2 1.366(3) . ?
C1 C10 1.417(3) . ?
C1 C11 1.511(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.423(2) . ?
C3 C4 1.409(3) . ?
C3 C8 1.416(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.360(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.428(2) . ?
C8 C9 1.408(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.371(3) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.510(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.323(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.495(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O3 H3 0.8400 . ?
O3 C29 1.436(2) . ?
O4 C26 1.417(3) . ?
O4 C30 1.428(2) . ?
C16 C17 1.352(3) . ?
C16 C25 1.423(3) . ?
C16 C26 1.520(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.428(2) . ?
C18 C19 1.407(3) . ?
C18 C23 1.419(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.370(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.417(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.351(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.430(3) . ?
C23 C24 1.406(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.369(3) . ?
C25 H25 0.9500 . ?
C26 H26 1.0000 . ?
C26 C27 1.506(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.323(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.495(3) . ?
C29 H29 1.0000 . ?
C29 C30 1.511(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?

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 O1 C11 110.70(16) . . ?
C14 O2 H2 109.5 . . ?
C2 C1 C10 119.66(16) . . ?
C2 C1 C11 119.86(18) . . ?
C10 C1 C11 120.41(18) . . ?
C1 C2 H2A 119.3 . . ?
C1 C2 C3 121.38(19) . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 C8 119.85(17) . . ?
C8 C3 C2 118.51(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.88(19) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 117.8(2) . . ?
C9 C8 C3 119.16(17) . . ?
C9 C8 C7 123.0(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.4 . . ?
C1 C10 H10 119.9 . . ?
C9 C10 C1 120.14(19) . . ?
C9 C10 H10 119.9 . . ?
O1 C11 C1 109.00(18) . . ?
O1 C11 H11 108.3 . . ?
O1 C11 C12 111.17(16) . . ?
C1 C11 H11 108.3 . . ?
C12 C11 C1 111.70(15) . . ?
C12 C11 H11 108.3 . . ?
C11 C12 H12 118.8 . . ?
C13 C12 C11 122.4(2) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.54(18) . . ?
C14 C13 H13 119.2 . . ?
O2 C14 C13 108.14(18) . . ?
O2 C14 H14 109.6 . . ?
O2 C14 C15 110.02(15) . . ?
C13 C14 H14 109.6 . . ?
C13 C14 C15 109.73(17) . . ?
C15 C14 H14 109.6 . . ?
O1 C15 C14 109.96(14) . . ?
O1 C15 H15A 109.7 . . ?
O1 C15 H15B 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C29 O3 H3 109.5 . . ?
C26 O4 C30 112.19(16) . . ?
C17 C16 C25 119.46(18) . . ?
C17 C16 C26 122.35(19) . . ?
C25 C16 C26 118.17(19) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.5(2) . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 C23 119.60(18) . . ?
C23 C18 C17 118.5(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.39(19) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 C22 118.1(2) . . ?
C24 C23 C18 119.18(18) . . ?
C24 C23 C22 122.7(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.6 . . ?
C16 C25 H25 119.7 . . ?
C24 C25 C16 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
O4 C26 C16 108.90(17) . . ?
O4 C26 H26 107.9 . . ?
O4 C26 C27 110.89(19) . . ?
C16 C26 H26 107.9 . . ?
C27 C26 C16 113.06(14) . . ?
C27 C26 H26 107.9 . . ?
C26 C27 H27 118.9 . . ?
C28 C27 C26 122.24(19) . . ?
C28 C27 H27 118.9 . . ?
C27 C28 H28 118.9 . . ?
C27 C28 C29 122.20(16) . . ?
C29 C28 H28 118.9 . . ?
O3 C29 C28 110.67(17) . . ?
O3 C29 H29 109.6 . . ?
O3 C29 C30 108.27(17) . . ?
C28 C29 H29 109.6 . . ?
C28 C29 C30 109.12(19) . . ?
C30 C29 H29 109.6 . . ?
O4 C30 C29 110.19(16) . . ?
O4 C30 H30A 109.6 . . ?
O4 C30 H30B 109.6 . . ?
C29 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C13 -14.8(3) . . . . ?
O2 C14 C15 O1 167.68(19) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C1 C2 C3 C8 0.6(3) . . . . ?
C1 C11 C12 C13 -136.8(2) . . . . ?
C2 C1 C10 C9 0.3(3) . . . . ?
C2 C1 C11 O1 131.5(2) . . . . ?
C2 C1 C11 C12 -105.2(2) . . . . ?
C2 C3 C4 C5 179.3(2) . . . . ?
C2 C3 C8 C7 -179.2(2) . . . . ?
C2 C3 C8 C9 -0.1(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C8 C9 C10 -0.3(3) . . . . ?
C4 C3 C8 C7 1.2(3) . . . . ?
C4 C3 C8 C9 -179.7(2) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C3 -0.5(4) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
C7 C8 C9 C10 178.8(2) . . . . ?
C8 C3 C4 C5 -1.1(3) . . . . ?
C8 C9 C10 C1 0.2(3) . . . . ?
C10 C1 C2 C3 -0.8(3) . . . . ?
C10 C1 C11 O1 -51.4(2) . . . . ?
C10 C1 C11 C12 71.8(3) . . . . ?
C11 O1 C15 C14 -69.2(2) . . . . ?
C11 C1 C2 C3 176.31(18) . . . . ?
C11 C1 C10 C9 -176.71(19) . . . . ?
C11 C12 C13 C14 -2.2(3) . . . . ?
C12 C13 C14 O2 -134.4(2) . . . . ?
C12 C13 C14 C15 -14.4(3) . . . . ?
C13 C14 C15 O1 48.8(2) . . . . ?
C15 O1 C11 C1 173.62(13) . . . . ?
C15 O1 C11 C12 50.07(18) . . . . ?
O3 C29 C30 O4 169.1(2) . . . . ?
O4 C26 C27 C28 -13.1(3) . . . . ?
C16 C17 C18 C19 -179.0(2) . . . . ?
C16 C17 C18 C23 0.6(3) . . . . ?
C16 C26 C27 C28 -135.7(3) . . . . ?
C17 C16 C25 C24 -1.7(3) . . . . ?
C17 C16 C26 O4 1.9(3) . . . . ?
C17 C16 C26 C27 125.7(3) . . . . ?
C17 C18 C19 C20 -179.6(2) . . . . ?
C17 C18 C23 C22 179.0(2) . . . . ?
C17 C18 C23 C24 -1.1(3) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C18 C23 C24 C25 0.1(3) . . . . ?
C19 C18 C23 C22 -1.3(3) . . . . ?
C19 C18 C23 C24 178.6(2) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C18 1.1(4) . . . . ?
C21 C22 C23 C24 -178.8(3) . . . . ?
C22 C23 C24 C25 -180.0(2) . . . . ?
C23 C18 C19 C20 0.8(4) . . . . ?
C23 C24 C25 C16 1.3(4) . . . . ?
C25 C16 C17 C18 0.7(3) . . . . ?
C25 C16 C26 O4 -179.6(2) . . . . ?
C25 C16 C26 C27 -55.9(3) . . . . ?
C26 O4 C30 C29 -68.6(3) . . . . ?
C26 C16 C17 C18 179.17(19) . . . . ?
C26 C16 C25 C24 179.81(19) . . . . ?
C26 C27 C28 C29 -2.5(4) . . . . ?
C27 C28 C29 O3 -134.1(2) . . . . ?
C27 C28 C29 C30 -15.0(3) . . . . ?
C28 C29 C30 O4 48.5(3) . . . . ?
C30 O4 C26 C16 173.24(18) . . . . ?
C30 O4 C26 C27 48.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.887
_oxdiff_exptl_absorpt_empirical_full_min 0.309

# start Validation Reply Form
_vrf_PLAT915_2023-77             
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         33 %     
RESPONSE: This crystal has good quality, although the Friedel 
Pair Coverage collection is not satisfactory, the configuration 
can be determined based on the key parameter flare (0.04 (9)).
;
# end Validation Reply Form
####################################################################### 
# 
# 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_34-2_2
_database_code_depnum_ccdc_archive 'CCDC 2408494'
loop_
_audit_author_name
_audit_author_address
'HUI YAO'
;China Three Gorges University
China
;
_audit_update_record             
;
2024-12-08 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-09-20
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 O5, 0.5(H2 O)'
_chemical_formula_sum            'C14 H21 O5.50'
_chemical_formula_weight         277.31
_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 0.0181 0.0091 '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 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.83690(10)
_cell_length_b                   14.8689(3)
_cell_length_c                   37.6287(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2706.23(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14910
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.8180
_cell_measurement_theta_min      3.1410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            25257
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.971
_diffrn_reflns_theta_min         2.348
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  31.00   1.00    1.00    --  -40.73  52.00  27.00   99
  2  ω    -34.00  65.00   1.00    1.00    --   40.73 -38.00 150.00   99
  3  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00-150.00   81
  4  ω     23.00  97.00   1.00    1.00    --   40.73-125.00 -60.00   74
  5  ω     94.00 178.00   1.00    1.66    --  107.58 125.00 -60.00   84
  6  ω     75.00 178.00   1.00    1.66    --  107.58  77.00   0.00  103
  7  ω     31.00 140.00   1.00    1.66    --  107.58 -77.00-120.00  109
  8  ω     94.00 178.00   1.00    1.66    --  107.58 125.00-120.00   84
  9  ω     94.00 178.00   1.00    1.66    --  107.58 125.00 -90.00   84
 10  ω     34.00 122.00   1.00    1.66    --  107.58-125.00 120.00   88
 11  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00-180.00  100
 12  ω   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00   0.00  109
 13  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00  90.00  100
 14  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00-120.00   99
 15  ω     79.00 178.00   1.00    1.66    --  107.58  30.00-150.00   99
 16  ω     79.00 178.00   1.00    1.66    --  107.58  30.00 -60.00   99
 17  ω     82.00 178.00   1.00    1.66    --  107.58  45.00  90.00   96
 18  ω     82.00 129.00   1.00    1.66    --  107.58  45.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1413662000
_diffrn_orient_matrix_UB_12      -0.0472830000
_diffrn_orient_matrix_UB_13      -0.0315806000
_diffrn_orient_matrix_UB_21      -0.1428136000
_diffrn_orient_matrix_UB_22      -0.0889104000
_diffrn_orient_matrix_UB_23      0.0102346000
_diffrn_orient_matrix_UB_31      -0.2470167000
_diffrn_orient_matrix_UB_32      0.0243390000
_diffrn_orient_matrix_UB_33      -0.0239816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                5194
_reflns_number_total             5394
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 2029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.7002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1012
_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, All O(H,H) groups
2.a Free rotating group:
 O11(H11A,H11B)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3A), C4(H4A), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C20(H20A,H20B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C23(H23), C24(H24), C26(H26), C27(H27)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C28(H28A,H28B,H28C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O6(H6), O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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 0.9329(4) 0.59041(11) 0.71674(5) 0.0228(4) Uani 1 1 d . . . . .
H1 H 0.889176 0.620367 0.734808 0.034 Uiso 1 1 calc R U . . .
O2 O 0.5396(3) 0.65963(11) 0.63925(4) 0.0171(3) Uani 1 1 d . . . . .
O3 O 0.6188(4) 0.78348(11) 0.69826(4) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.603207 0.839704 0.697360 0.030 Uiso 1 1 calc R U . . .
O4 O 0.9348(4) 0.90680(11) 0.65349(5) 0.0198(4) Uani 1 1 d . . . . .
H4 H 0.786976 0.934246 0.657932 0.030 Uiso 1 1 calc R U . . .
O5 O 0.6519(4) 0.87405(11) 0.59130(5) 0.0202(4) Uani 1 1 d . . . . .
C1 C 0.5703(5) 0.71240(16) 0.60759(6) 0.0165(5) Uani 1 1 d . . . . .
H1A H 0.386872 0.711372 0.595326 0.020 Uiso 1 1 calc R U . . .
C2 C 0.6196(5) 0.81134(15) 0.61948(6) 0.0163(5) Uani 1 1 d . . . . .
H2 H 0.456209 0.830528 0.633892 0.020 Uiso 1 1 calc R U . . .
C3 C 0.8734(5) 0.81664(15) 0.64323(6) 0.0160(5) Uani 1 1 d . . . . .
H3A H 1.034331 0.793743 0.629209 0.019 Uiso 1 1 calc R U . . .
C4 C 0.8388(5) 0.75536(15) 0.67539(6) 0.0166(5) Uani 1 1 d . . . . .
H4A H 1.015378 0.754540 0.689204 0.020 Uiso 1 1 calc R U . . .
C5 C 0.7770(5) 0.66072(15) 0.66218(6) 0.0166(5) Uani 1 1 d . . . . .
H5 H 0.940477 0.638465 0.648488 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7119(5) 0.59334(16) 0.69147(6) 0.0194(5) Uani 1 1 d . . . . .
H6A H 0.538365 0.610875 0.703588 0.023 Uiso 1 1 calc R U . . .
H6B H 0.684968 0.532917 0.680979 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3997(6) 0.90100(19) 0.57571(8) 0.0305(6) Uani 1 1 d . . . . .
H7A H 0.432052 0.952782 0.560144 0.046 Uiso 1 1 calc R U . . .
H7B H 0.268441 0.917720 0.594416 0.046 Uiso 1 1 calc R U . . .
H7C H 0.323516 0.851188 0.561743 0.046 Uiso 1 1 calc R U . . .
C8 C 0.7772(5) 0.67069(17) 0.58187(6) 0.0179(5) Uani 1 1 d . . . . .
C9 C 0.8430(6) 0.57943(17) 0.58442(7) 0.0254(6) Uani 1 1 d . . . . .
H9 H 0.763880 0.544224 0.602874 0.031 Uiso 1 1 calc R U . . .
C10 C 1.0218(6) 0.53970(19) 0.56041(7) 0.0302(6) Uani 1 1 d . . . . .
H10 H 1.063730 0.477595 0.562889 0.036 Uiso 1 1 calc R U . . .
C11 C 1.1419(5) 0.58765(19) 0.53284(7) 0.0262(6) Uani 1 1 d . . . . .
C12 C 0.8927(6) 0.71849(17) 0.55386(6) 0.0215(5) Uani 1 1 d . . . . .
H12 H 0.847824 0.780270 0.550981 0.026 Uiso 1 1 calc R U . . .
C13 C 1.0734(6) 0.67769(19) 0.52982(7) 0.0254(6) Uani 1 1 d . . . . .
H13 H 1.150720 0.712341 0.511084 0.030 Uiso 1 1 calc R U . . .
C14 C 1.3430(7) 0.5440(2) 0.50754(8) 0.0384(7) Uani 1 1 d . . . . .
H14A H 1.355607 0.579975 0.485771 0.058 Uiso 1 1 calc R U . . .
H14B H 1.278540 0.483342 0.501664 0.058 Uiso 1 1 calc R U . . .
H14C H 1.525550 0.540428 0.518746 0.058 Uiso 1 1 calc R U . . .
O6 O 0.6547(4) 0.35383(11) 0.72193(5) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.504331 0.381090 0.724877 0.033 Uiso 1 1 calc R U . . .
O7 O 0.2929(4) 0.20942(11) 0.73594(5) 0.0198(4) Uani 1 1 d . . . . .
H7 H 0.343(9) 0.241(3) 0.7544(11) 0.053(12) Uiso 1 1 d . . . . .
O8 O 0.4325(4) -0.03733(11) 0.68000(5) 0.0221(4) Uani 1 1 d . . . . .
H8 H 0.278925 -0.051752 0.671282 0.033 Uiso 1 1 calc R U . . .
O9 O 0.2895(3) 0.14888(10) 0.66225(4) 0.0163(3) Uani 1 1 d . . . . .
O10 O 0.4643(4) 0.38990(11) 0.65320(5) 0.0207(4) Uani 1 1 d . . . . .
C15 C 0.2273(6) 0.43796(18) 0.64187(8) 0.0302(6) Uani 1 1 d . . . . .
H15A H 0.135869 0.404803 0.622668 0.045 Uiso 1 1 calc R U . . .
H15B H 0.282834 0.497454 0.633229 0.045 Uiso 1 1 calc R U . . .
H15C H 0.099203 0.444862 0.661860 0.045 Uiso 1 1 calc R U . . .
C16 C 0.3974(5) 0.30653(15) 0.66930(6) 0.0163(5) Uani 1 1 d . . . . .
H16 H 0.219398 0.314890 0.682401 0.020 Uiso 1 1 calc R U . . .
C17 C 0.6180(5) 0.28386(15) 0.69663(6) 0.0168(5) Uani 1 1 d . . . . .
H17 H 0.797132 0.274143 0.683939 0.020 Uiso 1 1 calc R U . . .
C18 C 0.5388(5) 0.19679(15) 0.71550(6) 0.0167(5) Uani 1 1 d . . . . .
H18 H 0.692773 0.178493 0.731699 0.020 Uiso 1 1 calc R U . . .
C19 C 0.4937(5) 0.12359(16) 0.68799(6) 0.0159(5) Uani 1 1 d . . . . .
H19 H 0.672383 0.112332 0.675388 0.019 Uiso 1 1 calc R U . . .
C20 C 0.3958(5) 0.03632(15) 0.70424(6) 0.0190(5) Uani 1 1 d . . . . .
H20A H 0.500991 0.024389 0.726315 0.023 Uiso 1 1 calc R U . . .
H20B H 0.197806 0.041584 0.710571 0.023 Uiso 1 1 calc R U . . .
C21 C 0.3543(5) 0.22844(15) 0.64239(6) 0.0160(5) Uani 1 1 d . . . . .
H21 H 0.183152 0.243787 0.628779 0.019 Uiso 1 1 calc R U . . .
C22 C 0.5786(5) 0.21258(16) 0.61467(6) 0.0168(5) Uani 1 1 d . . . . .
C23 C 0.6712(5) 0.12590(17) 0.60703(6) 0.0203(5) Uani 1 1 d . . . . .
H23 H 0.600628 0.076610 0.620286 0.024 Uiso 1 1 calc R U . . .
C24 C 0.8648(5) 0.11009(17) 0.58041(6) 0.0225(5) Uani 1 1 d . . . . .
H24 H 0.926438 0.050354 0.576222 0.027 Uiso 1 1 calc R U . . .
C25 C 0.9699(5) 0.17953(18) 0.55983(6) 0.0223(5) Uani 1 1 d . . . . .
C26 C 0.6795(5) 0.28227(17) 0.59329(6) 0.0201(5) Uani 1 1 d . . . . .
H26 H 0.615564 0.341903 0.597121 0.024 Uiso 1 1 calc R U . . .
C27 C 0.8713(6) 0.26589(17) 0.56657(6) 0.0225(5) Uani 1 1 d . . . . .
H27 H 0.936663 0.314662 0.552592 0.027 Uiso 1 1 calc R U . . .
C28 C 1.1815(6) 0.1633(2) 0.53125(7) 0.0295(6) Uani 1 1 d . . . . .
H28A H 1.121175 0.192137 0.509166 0.044 Uiso 1 1 calc R U . . .
H28B H 1.201607 0.098418 0.527344 0.044 Uiso 1 1 calc R U . . .
H28C H 1.359481 0.188585 0.538635 0.044 Uiso 1 1 calc R U . . .
O11 O 1.1569(4) 0.42896(12) 0.74120(5) 0.0269(4) Uani 1 1 d G . . . .
H11A H 1.010304 0.397592 0.740033 0.040 Uiso 1 1 d G U . . .
H11B H 1.115122 0.478140 0.730988 0.040 Uiso 1 1 d G 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
O1 H1 0.8400 . ?
O1 C6 1.431(3) . ?
O2 C1 1.434(3) . ?
O2 C5 1.437(3) . ?
O3 H3 0.8400 . ?
O3 C4 1.431(3) . ?
O4 H4 0.8400 . ?
O4 C3 1.426(3) . ?
O5 C2 1.421(3) . ?
O5 C7 1.412(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.556(3) . ?
C1 C8 1.524(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.521(3) . ?
C3 H3A 1.0000 . ?
C3 C4 1.524(3) . ?
C4 H4A 1.0000 . ?
C4 C5 1.522(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.397(4) . ?
C8 C12 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 C13 1.384(4) . ?
C11 C14 1.508(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O6 H6 0.8400 . ?
O6 C17 1.421(3) . ?
O7 H7 0.87(4) . ?
O7 C18 1.429(3) . ?
O8 H8 0.8400 . ?
O8 C20 1.436(3) . ?
O9 C19 1.433(3) . ?
O9 C21 1.434(3) . ?
O10 C15 1.416(3) . ?
O10 C16 1.417(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.520(3) . ?
C16 C21 1.555(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.525(3) . ?
C18 H18 1.0000 . ?
C18 C19 1.518(3) . ?
C19 H19 1.0000 . ?
C19 C20 1.511(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 1.0000 . ?
C21 C22 1.524(3) . ?
C22 C23 1.394(3) . ?
C22 C26 1.399(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(4) . ?
C25 C27 1.393(4) . ?
C25 C28 1.504(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.390(4) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8503 . ?

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
C6 O1 H1 109.5 . . ?
C1 O2 C5 114.21(17) . . ?
C4 O3 H3 109.5 . . ?
C3 O4 H4 109.5 . . ?
C7 O5 C2 113.66(19) . . ?
O2 C1 H1A 106.4 . . ?
O2 C1 C2 107.11(18) . . ?
O2 C1 C8 111.89(19) . . ?
C2 C1 H1A 106.4 . . ?
C8 C1 H1A 106.4 . . ?
C8 C1 C2 117.8(2) . . ?
O5 C2 C1 115.02(19) . . ?
O5 C2 H2 107.7 . . ?
O5 C2 C3 108.41(19) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 C1 109.98(18) . . ?
C3 C2 H2 107.7 . . ?
O4 C3 C2 112.08(19) . . ?
O4 C3 H3A 107.5 . . ?
O4 C3 C4 111.70(19) . . ?
C2 C3 H3A 107.5 . . ?
C2 C3 C4 110.30(19) . . ?
C4 C3 H3A 107.5 . . ?
O3 C4 C3 112.61(18) . . ?
O3 C4 H4A 109.0 . . ?
O3 C4 C5 108.70(19) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 C3 108.36(19) . . ?
C5 C4 H4A 109.0 . . ?
O2 C5 C4 111.31(18) . . ?
O2 C5 H5 108.6 . . ?
O2 C5 C6 105.19(19) . . ?
C4 C5 H5 108.6 . . ?
C4 C5 C6 114.4(2) . . ?
C6 C5 H5 108.6 . . ?
O1 C6 C5 110.3(2) . . ?
O1 C6 H6A 109.6 . . ?
O1 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C1 120.1(2) . . ?
C12 C8 C1 122.5(2) . . ?
C12 C8 C9 117.2(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 122.1(3) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C14 121.4(3) . . ?
C13 C11 C10 117.3(2) . . ?
C13 C11 C14 121.3(3) . . ?
C8 C12 H12 119.3 . . ?
C8 C12 C13 121.4(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C13 C12 121.1(2) . . ?
C11 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 O6 H6 109.5 . . ?
C18 O7 H7 106(3) . . ?
C20 O8 H8 109.5 . . ?
C19 O9 C21 114.70(17) . . ?
C15 O10 C16 112.66(19) . . ?
O10 C15 H15A 109.5 . . ?
O10 C15 H15B 109.5 . . ?
O10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O10 C16 H16 107.4 . . ?
O10 C16 C17 108.86(19) . . ?
O10 C16 C21 113.92(18) . . ?
C17 C16 H16 107.4 . . ?
C17 C16 C21 111.67(19) . . ?
C21 C16 H16 107.4 . . ?
O6 C17 C16 112.25(19) . . ?
O6 C17 H17 108.5 . . ?
O6 C17 C18 109.93(19) . . ?
C16 C17 H17 108.5 . . ?
C16 C17 C18 109.10(19) . . ?
C18 C17 H17 108.5 . . ?
O7 C18 C17 110.36(18) . . ?
O7 C18 H18 109.1 . . ?
O7 C18 C19 109.97(18) . . ?
C17 C18 H18 109.1 . . ?
C19 C18 C17 109.09(19) . . ?
C19 C18 H18 109.1 . . ?
O9 C19 C18 111.83(18) . . ?
O9 C19 H19 108.6 . . ?
O9 C19 C20 106.45(19) . . ?
C18 C19 H19 108.6 . . ?
C20 C19 C18 112.63(19) . . ?
C20 C19 H19 108.6 . . ?
O8 C20 C19 111.04(19) . . ?
O8 C20 H20A 109.4 . . ?
O8 C20 H20B 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
O9 C21 C16 107.83(18) . . ?
O9 C21 H21 105.9 . . ?
O9 C21 C22 112.63(18) . . ?
C16 C21 H21 105.9 . . ?
C22 C21 C16 117.78(19) . . ?
C22 C21 H21 105.9 . . ?
C23 C22 C21 120.9(2) . . ?
C23 C22 C26 117.0(2) . . ?
C26 C22 C21 121.8(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.5(2) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C27 117.3(2) . . ?
C24 C25 C28 121.9(2) . . ?
C27 C25 C28 120.8(2) . . ?
C22 C26 H26 119.4 . . ?
C27 C26 C22 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C27 H27 119.3 . . ?
C26 C27 C25 121.5(2) . . ?
C26 C27 H27 119.3 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H11A O11 H11B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 O5 -179.35(18) . . . . ?
O2 C1 C2 C3 57.9(2) . . . . ?
O2 C1 C8 C9 20.6(3) . . . . ?
O2 C1 C8 C12 -163.9(2) . . . . ?
O2 C5 C6 O1 -178.41(17) . . . . ?
O3 C4 C5 O2 66.9(2) . . . . ?
O3 C4 C5 C6 -52.2(3) . . . . ?
O4 C3 C4 O3 60.3(3) . . . . ?
O4 C3 C4 C5 -179.42(18) . . . . ?
O5 C2 C3 O4 50.7(2) . . . . ?
O5 C2 C3 C4 175.88(17) . . . . ?
C1 O2 C5 C4 61.6(2) . . . . ?
C1 O2 C5 C6 -173.99(18) . . . . ?
C1 C2 C3 O4 177.27(18) . . . . ?
C1 C2 C3 C4 -57.6(2) . . . . ?
C1 C8 C9 C10 177.4(2) . . . . ?
C1 C8 C12 C13 -177.4(2) . . . . ?
C2 C1 C8 C9 145.4(2) . . . . ?
C2 C1 C8 C12 -39.1(3) . . . . ?
C2 C3 C4 O3 -65.0(2) . . . . ?
C2 C3 C4 C5 55.2(2) . . . . ?
C3 C4 C5 O2 -55.8(2) . . . . ?
C3 C4 C5 C6 -174.9(2) . . . . ?
C4 C5 C6 O1 -56.0(3) . . . . ?
C5 O2 C1 C2 -60.7(2) . . . . ?
C5 O2 C1 C8 69.8(2) . . . . ?
C7 O5 C2 C1 79.3(3) . . . . ?
C7 O5 C2 C3 -157.1(2) . . . . ?
C8 C1 C2 O5 53.5(3) . . . . ?
C8 C1 C2 C3 -69.2(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C8 C12 C13 C11 0.7(4) . . . . ?
C9 C8 C12 C13 -1.8(4) . . . . ?
C9 C10 C11 C13 -0.7(4) . . . . ?
C9 C10 C11 C14 178.2(3) . . . . ?
C10 C11 C13 C12 0.6(4) . . . . ?
C12 C8 C9 C10 1.7(4) . . . . ?
C14 C11 C13 C12 -178.3(3) . . . . ?
O6 C17 C18 O7 57.7(2) . . . . ?
O6 C17 C18 C19 178.62(18) . . . . ?
O7 C18 C19 O9 64.8(2) . . . . ?
O7 C18 C19 C20 -55.0(2) . . . . ?
O9 C19 C20 O8 74.1(2) . . . . ?
O9 C21 C22 C23 9.1(3) . . . . ?
O9 C21 C22 C26 -177.7(2) . . . . ?
O10 C16 C17 O6 54.8(2) . . . . ?
O10 C16 C17 C18 176.89(18) . . . . ?
O10 C16 C21 O9 179.79(18) . . . . ?
O10 C16 C21 C22 51.0(3) . . . . ?
C15 O10 C16 C17 -150.4(2) . . . . ?
C15 O10 C16 C21 84.3(3) . . . . ?
C16 C17 C18 O7 -65.8(2) . . . . ?
C16 C17 C18 C19 55.1(2) . . . . ?
C16 C21 C22 C23 135.6(2) . . . . ?
C16 C21 C22 C26 -51.2(3) . . . . ?
C17 C16 C21 O9 56.0(2) . . . . ?
C17 C16 C21 C22 -72.8(2) . . . . ?
C17 C18 C19 O9 -56.4(2) . . . . ?
C17 C18 C19 C20 -176.19(19) . . . . ?
C18 C19 C20 O8 -163.03(19) . . . . ?
C19 O9 C21 C16 -57.5(2) . . . . ?
C19 O9 C21 C22 74.1(2) . . . . ?
C21 O9 C19 C18 59.9(2) . . . . ?
C21 O9 C19 C20 -176.71(18) . . . . ?
C21 C16 C17 O6 -178.56(18) . . . . ?
C21 C16 C17 C18 -56.5(2) . . . . ?
C21 C22 C23 C24 176.4(2) . . . . ?
C21 C22 C26 C27 -175.9(2) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C22 C26 C27 C25 0.4(4) . . . . ?
C23 C22 C26 C27 -2.4(4) . . . . ?
C23 C24 C25 C27 -0.8(4) . . . . ?
C23 C24 C25 C28 179.3(2) . . . . ?
C24 C25 C27 C26 1.2(4) . . . . ?
C26 C22 C23 C24 2.9(4) . . . . ?
C28 C25 C27 C26 -178.9(2) . . . . ?

_olex2_date_sample_data_collection 2023-09-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.596
