# Supplementary Information (SI) for Green Chemistry.
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2401001'
loop_
_audit_author_name
_audit_author_address
'Yizhou Wang'
;Institution of Chemistry Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-11-27 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_audit_creation_date             2024-11-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O4'
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHO
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      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                   7.4833(6)
_cell_length_b                   8.3504(7)
_cell_length_c                   13.1170(8)
_cell_angle_alpha                87.703(6)
_cell_angle_beta                 79.960(6)
_cell_angle_gamma                63.498(8)
_cell_volume                     721.64(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6042
_cell_measurement_temperature    169.9(3)
_cell_measurement_theta_max      75.5260
_cell_measurement_theta_min      3.4100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
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    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8294
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.886
_diffrn_reflns_theta_min         3.425
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  15.00   0.50    0.05    --  -46.51  19.00-180.00   72
  2  ω    -18.00   8.00   0.50    0.05    --  -46.51  19.00-150.00   52
  3  ω    -18.00  12.00   0.50    0.05    --  -46.51  19.00 -90.00   60
  4  ω     24.00  71.00   0.50    0.05    --   46.51  77.00  90.00   94
  5  ω     73.00 119.00   0.50    0.05    --   46.51  77.00  90.00   92
  6  ω     93.00 147.00   0.50    0.05    --  105.35 103.00  96.00  108
  7  ω     83.00 176.00   0.50    0.05    --  105.35  77.00  60.00  186
  8  ω    118.00 166.00   0.50    0.05    --  105.35  15.00-180.00   96
  9  ω     33.00  66.00   0.50    0.05    --  105.35 -61.00-120.00   66
 10  ω     41.00  70.00   0.50    0.05    --  105.35 -61.00-150.00   58
 11  ω     35.00  75.00   0.50    0.05    --  105.35 -61.00-180.00   80
 12  ω     36.00  73.00   0.50    0.05    --  105.35 -61.00 -30.00   74
 13  ω     35.00  60.00   0.50    0.05    --  105.35 -61.00   0.00   50
 14  ω     33.00 108.00   0.50    0.05    --  105.35 -77.00 120.00  150
 15  ω     34.00  63.00   0.50    0.05    --  105.35 -61.00 150.00   58
 16  ω     78.00 104.00   0.50    0.05    --  105.35 -94.00 150.00   52
 17  ω     35.00 106.00   0.50    0.05    --  105.35-103.00  -5.00  142
 18  ω     36.00  73.00   0.50    0.05    --  105.35-125.00  30.00   74
 19  ω     78.00 111.00   0.50    0.05    --  105.35-125.00  30.00   66
 20  ω     38.00 109.00   0.50    0.05    --  105.35-125.00  90.00  142
 21  ω     60.00 105.00   0.50    0.05    --  105.35 -94.00  90.00   90
 22  ω     60.00  91.00   0.50    0.05    --   46.51-125.00 -30.00   62
 23  ω      0.00  82.00   0.50    0.05    --   46.51-103.00  -5.00  164
 24  ω     22.00  54.00   0.50    0.05    --   46.51-125.00 -30.00   64
 25  ω   -124.00 -89.00   0.50    0.05    -- -104.50 142.00-163.60   70
 26  ω   -111.00 -45.00   0.50    0.05    -- -104.50 125.00 -90.00  132
 27  ω    -82.00   7.00   0.50    0.05    --  -46.51 103.00  96.00  178
 28  ω   -106.00 -33.00   0.50    0.05    -- -104.50 103.00  96.00  146
 29  ω   -124.00 -88.00   0.50    0.05    -- -104.50 -15.00 120.00   72
 30  ω   -174.00-113.00   0.50    0.05    -- -104.50 -52.00  75.62  122
 31  ω   -165.00-139.00   0.50    0.05    -- -104.50 -45.00  90.00   52
 32  ω   -173.00-139.00   0.50    0.05    -- -104.50 -15.00 120.00   68
 33  ω   -135.00 -90.00   0.50    0.05    -- -104.50 -45.00  90.00   90
 34  ω   -160.00-106.00   0.50    0.05    -- -104.50 -45.00  30.00  108
 35  ω    -90.00 -54.00   0.50    0.05    --  -46.51 -38.00 -30.00   72
 36  ω   -174.00 -85.00   0.50    0.05    -- -104.50-103.00  -5.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0850408000
_diffrn_orient_matrix_UB_12      -0.1410122000
_diffrn_orient_matrix_UB_13      0.0805337000
_diffrn_orient_matrix_UB_21      -0.1891124000
_diffrn_orient_matrix_UB_22      0.1093720000
_diffrn_orient_matrix_UB_23      0.0813370000
_diffrn_orient_matrix_UB_31      -0.1076747000
_diffrn_orient_matrix_UB_32      -0.1035831000
_diffrn_orient_matrix_UB_33      -0.0339269000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2631
_reflns_number_total             2898
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0118(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.062
_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)+(0.0514P)²+0.1999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1032
_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 Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C2(H2), C8(H8), C5(H5), C3(H3), C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C16(H16A,H16B,H16C)
;
_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 0.78624(14) 0.45525(12) 0.43356(7) 0.0337(2) Uani 1 1 d . . . . .
O4 O 0.66114(14) 0.74968(12) 0.40613(7) 0.0341(2) Uani 1 1 d . . . . .
O2 O 0.92321(13) 0.54256(13) 0.19631(7) 0.0335(2) Uani 1 1 d . . . . .
O1 O 0.89384(14) 0.69069(12) 0.04908(7) 0.0360(2) Uani 1 1 d . . . . .
C11 C 0.64390(16) 0.42773(15) 0.16784(9) 0.0217(2) Uani 1 1 d . . . . .
C17 C 0.66943(18) 0.58739(16) 0.39688(9) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.63666(17) 0.59915(15) 0.12083(9) 0.0221(3) Uani 1 1 d . . . . .
H9 H 0.611813 0.599916 0.048293 0.027 Uiso 1 1 calc R U . . .
C12 C 0.58007(17) 0.42338(15) 0.27357(9) 0.0228(3) Uani 1 1 d . . . . .
C15 C 0.83245(17) 0.61583(15) 0.11583(9) 0.0239(3) Uani 1 1 d . . . . .
C13 C 0.40031(17) 0.76029(15) 0.28520(9) 0.0230(3) Uani 1 1 d . . . . .
C14 C 0.46375(17) 0.76463(15) 0.17938(9) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.71105(18) 0.27435(16) 0.10436(10) 0.0270(3) Uani 1 1 d . . . . .
H1 H 0.756201 0.276779 0.032246 0.032 Uiso 1 1 calc R U . . .
C10 C 0.50280(17) 0.59119(15) 0.34254(9) 0.0231(3) Uani 1 1 d . . . . .
H10 H 0.395334 0.587302 0.398368 0.028 Uiso 1 1 calc R U . . .
C4 C 0.58237(19) 0.26568(17) 0.31460(10) 0.0294(3) Uani 1 1 d . . . . .
H4 H 0.539531 0.261909 0.386849 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7123(2) 0.11834(17) 0.14591(11) 0.0324(3) Uani 1 1 d . . . . .
H2 H 0.758148 0.014518 0.102292 0.039 Uiso 1 1 calc R U . . .
C8 C 0.36654(19) 0.92035(16) 0.12697(10) 0.0295(3) Uani 1 1 d . . . . .
H8 H 0.410433 0.923236 0.054755 0.035 Uiso 1 1 calc R U . . .
C5 C 0.23752(18) 0.91195(17) 0.33684(10) 0.0314(3) Uani 1 1 d . . . . .
H5 H 0.191536 0.909284 0.408828 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6466(2) 0.11425(17) 0.25090(11) 0.0344(3) Uani 1 1 d . . . . .
H3 H 0.645482 0.008212 0.279350 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2069(2) 1.07053(17) 0.17925(12) 0.0369(3) Uani 1 1 d . . . . .
H7 H 0.141945 1.176049 0.143066 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1420(2) 1.06648(18) 0.28439(12) 0.0379(3) Uani 1 1 d . . . . .
H6 H 0.032473 1.169215 0.320561 0.045 Uiso 1 1 calc R U . . .
C18 C 0.8073(3) 0.7602(2) 0.46137(13) 0.0457(4) Uani 1 1 d . . . . .
H18A H 0.944596 0.676370 0.428372 0.069 Uiso 1 1 calc R U . . .
H18B H 0.781989 0.728903 0.533479 0.069 Uiso 1 1 calc R U . . .
H18C H 0.794190 0.882325 0.459672 0.069 Uiso 1 1 calc R U . . .
C16 C 1.1082(2) 0.5558(2) 0.19975(13) 0.0473(4) Uani 1 1 d . . . . .
H16A H 1.208977 0.493313 0.138347 0.071 Uiso 1 1 calc R U . . .
H16B H 1.160886 0.500809 0.262302 0.071 Uiso 1 1 calc R U . . .
H16C H 1.080137 0.682144 0.200943 0.071 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
O3 C17 1.2068(15) . ?
O4 C17 1.3382(15) . ?
O4 C18 1.4477(16) . ?
O2 C15 1.3332(15) . ?
O2 C16 1.4453(15) . ?
O1 C15 1.2002(14) . ?
C11 C9 1.5178(15) . ?
C11 C12 1.3904(16) . ?
C11 C1 1.3970(17) . ?
C17 C10 1.5286(16) . ?
C9 H9 1.0000 . ?
C9 C15 1.5226(16) . ?
C9 C14 1.5219(16) . ?
C12 C10 1.5207(16) . ?
C12 C4 1.3966(16) . ?
C13 C14 1.3909(16) . ?
C13 C10 1.5158(16) . ?
C13 C5 1.3967(17) . ?
C14 C8 1.3969(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3887(17) . ?
C10 H10 1.0000 . ?
C4 H4 0.9500 . ?
C4 C3 1.3893(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.3836(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.3844(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3879(19) . ?
C3 H3 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.384(2) . ?
C6 H6 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C17 O4 C18 116.12(10) . . ?
C15 O2 C16 115.83(10) . . ?
C12 C11 C9 120.36(10) . . ?
C12 C11 C1 119.70(10) . . ?
C1 C11 C9 119.92(10) . . ?
O3 C17 O4 123.78(11) . . ?
O3 C17 C10 123.67(11) . . ?
O4 C17 C10 112.36(10) . . ?
C11 C9 H9 107.7 . . ?
C11 C9 C15 113.69(9) . . ?
C11 C9 C14 111.76(9) . . ?
C15 C9 H9 107.7 . . ?
C14 C9 H9 107.7 . . ?
C14 C9 C15 108.08(9) . . ?
C11 C12 C10 119.84(10) . . ?
C11 C12 C4 119.35(11) . . ?
C4 C12 C10 120.78(11) . . ?
O2 C15 C9 111.75(9) . . ?
O1 C15 O2 124.31(11) . . ?
O1 C15 C9 123.91(11) . . ?
C14 C13 C10 120.23(10) . . ?
C14 C13 C5 119.03(11) . . ?
C5 C13 C10 120.71(11) . . ?
C13 C14 C9 119.97(10) . . ?
C13 C14 C8 119.79(11) . . ?
C8 C14 C9 120.23(11) . . ?
C11 C1 H1 119.8 . . ?
C2 C1 C11 120.48(12) . . ?
C2 C1 H1 119.8 . . ?
C17 C10 H10 106.3 . . ?
C12 C10 C17 110.94(9) . . ?
C12 C10 H10 106.3 . . ?
C13 C10 C17 114.43(9) . . ?
C13 C10 C12 111.95(9) . . ?
C13 C10 H10 106.3 . . ?
C12 C4 H4 119.6 . . ?
C3 C4 C12 120.71(12) . . ?
C3 C4 H4 119.6 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.94(12) . . ?
C3 C2 H2 120.0 . . ?
C14 C8 H8 119.7 . . ?
C7 C8 C14 120.64(12) . . ?
C7 C8 H8 119.7 . . ?
C13 C5 H5 119.6 . . ?
C6 C5 C13 120.89(13) . . ?
C6 C5 H5 119.6 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.80(11) . . ?
C2 C3 H3 120.1 . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.81(12) . . ?
C6 C7 H7 120.1 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.83(12) . . ?
C7 C6 H6 120.1 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 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
O3 C17 C10 C12 -41.26(15) . . . . ?
O3 C17 C10 C13 -169.09(11) . . . . ?
O4 C17 C10 C12 143.53(10) . . . . ?
O4 C17 C10 C13 15.69(14) . . . . ?
C11 C9 C15 O2 -34.19(13) . . . . ?
C11 C9 C15 O1 147.91(11) . . . . ?
C11 C9 C14 C13 30.95(14) . . . . ?
C11 C9 C14 C8 -148.20(10) . . . . ?
C11 C12 C10 C17 -98.07(12) . . . . ?
C11 C12 C10 C13 31.10(14) . . . . ?
C11 C12 C4 C3 -0.31(18) . . . . ?
C11 C1 C2 C3 0.01(19) . . . . ?
C9 C11 C12 C10 -0.07(15) . . . . ?
C9 C11 C12 C4 178.08(10) . . . . ?
C9 C11 C1 C2 -177.93(11) . . . . ?
C9 C14 C8 C7 178.89(11) . . . . ?
C12 C11 C9 C15 91.77(12) . . . . ?
C12 C11 C9 C14 -30.92(14) . . . . ?
C12 C11 C1 C2 0.74(17) . . . . ?
C12 C4 C3 C2 1.06(19) . . . . ?
C15 C9 C14 C13 -94.89(12) . . . . ?
C15 C9 C14 C8 85.96(12) . . . . ?
C13 C14 C8 C7 -0.26(17) . . . . ?
C13 C5 C6 C7 0.73(19) . . . . ?
C14 C9 C15 O2 90.50(11) . . . . ?
C14 C9 C15 O1 -87.40(13) . . . . ?
C14 C13 C10 C17 96.25(12) . . . . ?
C14 C13 C10 C12 -31.07(14) . . . . ?
C14 C13 C5 C6 -1.24(18) . . . . ?
C14 C8 C7 C6 -0.26(19) . . . . ?
C1 C11 C9 C15 -89.56(13) . . . . ?
C1 C11 C9 C14 147.75(10) . . . . ?
C1 C11 C12 C10 -178.74(10) . . . . ?
C1 C11 C12 C4 -0.58(16) . . . . ?
C1 C2 C3 C4 -0.90(19) . . . . ?
C10 C12 C4 C3 177.83(11) . . . . ?
C10 C13 C14 C9 0.00(15) . . . . ?
C10 C13 C14 C8 179.15(10) . . . . ?
C10 C13 C5 C6 -179.38(11) . . . . ?
C4 C12 C10 C17 83.80(13) . . . . ?
C4 C12 C10 C13 -147.03(11) . . . . ?
C8 C7 C6 C5 0.0(2) . . . . ?
C5 C13 C14 C9 -178.16(10) . . . . ?
C5 C13 C14 C8 0.99(16) . . . . ?
C5 C13 C10 C17 -85.62(13) . . . . ?
C5 C13 C10 C12 147.06(11) . . . . ?
C18 O4 C17 O3 1.81(18) . . . . ?
C18 O4 C17 C10 177.01(11) . . . . ?
C16 O2 C15 O1 -0.62(18) . . . . ?
C16 O2 C15 C9 -178.51(11) . . . . ?

_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 1.750
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_tx17159_auto
_database_code_depnum_ccdc_archive 'CCDC 2416815'
loop_
_audit_author_name
_audit_author_address
'Wang Yizhou'
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-01-14 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_audit_creation_date             2025-01-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 O2'
_chemical_formula_sum            'C7 H5 O2'
_chemical_formula_weight         121.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHO
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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.56956(10)
_cell_length_b                   10.83565(18)
_cell_length_c                   18.2517(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1101.49(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8410
_cell_measurement_temperature    170.0(4)
_cell_measurement_theta_max      75.1530
_cell_measurement_theta_min      4.8430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
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    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11646
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.681
_diffrn_reflns_theta_min         4.846
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  47.00   0.50    0.05    --   42.87  57.00 -60.00   50
  2  ω     73.00  99.00   0.50    0.05    --   42.87  57.00 -60.00   52
  3  ω     21.00 116.00   0.50    0.05    --   42.87  61.00-179.00  190
  4  ω     21.00  81.00   0.50    0.05    --   42.87-125.00 -30.00  120
  5  ω     37.00 111.00   0.50    0.07    --  108.44-125.00-150.00  148
  6  ω     37.00  76.00   0.50    0.07    --  108.44-125.00 -90.00   78
  7  ω     80.00 105.00   0.50    0.07    --  108.44-125.00 -90.00   50
  8  ω     36.00  66.00   0.50    0.07    --  108.44-108.00  22.57   60
  9  ω     70.00 107.00   0.50    0.07    --  108.44-108.00  22.57   74
 10  ω     73.00 110.00   0.50    0.07    --  108.44-125.00  30.00   74
 11  ω     36.00  82.00   0.50    0.07    --  108.44 -94.00 -90.00   92
 12  ω     36.00 104.00   0.50    0.07    --  108.44 -94.00  30.00  136
 13  ω     63.00 104.00   0.50    0.07    --  108.44 -94.00  60.00   82
 14  ω     39.00  80.00   0.50    0.07    --  108.44-125.00 120.00   82
 15  ω     64.00  89.00   0.50    0.07    --  108.44 -77.00 120.00   50
 16  ω     34.00  75.00   0.50    0.07    --  108.44 -61.00  42.00   82
 17  ω    -30.00  65.00   0.50    0.05    --   42.87 -61.00  42.00  190
 18  ω     85.00 178.00   0.50    0.07    --  108.44  30.00 120.00  186
 19  ω     86.00 132.00   0.50    0.07    --  108.44  30.00 -30.00   92
 20  ω    141.00 167.00   0.50    0.07    --  108.44  30.00 -30.00   52
 21  ω     85.00 178.00   0.50    0.07    --  108.44  61.00-179.00  186
 22  ω    127.00 174.00   0.50    0.07    --  108.44 125.00-120.00   94
 23  ω     82.00 170.00   0.50    0.07    --  108.44 125.00   0.00  176
 24  ω     80.00 114.00   0.50    0.07    --  108.44 125.00-120.00   68
 25  ω   -116.00 -19.00   0.50    0.05    --  -42.87 -61.00  42.00  194
 26  ω   -160.00-121.00   0.50    0.07    -- -104.50 -72.00 131.82   78
 27  ω   -174.00 -81.00   0.50    0.07    -- -104.50 -61.00  42.00  186
 28  ω   -127.00 -86.00   0.50    0.07    -- -104.50 -30.00 -90.00   82
 29  ω   -169.00-133.00   0.50    0.07    -- -104.50 -30.00 -90.00   72
 30  ω   -169.00-135.00   0.50    0.07    -- -104.50-125.00-150.00   68
 31  ω    -22.00  37.00   0.50    0.05    --  -42.87  19.00 150.00  118
 32  ω    -59.00 -32.00   0.50    0.07    -- -104.50  61.00  30.00   54
 33  ω   -132.00 -90.00   0.50    0.07    -- -104.50-125.00-150.00   84
 34  ω    -60.00  23.00   0.50    0.05    --  -42.87  61.00-179.00  166
 35  ω    -68.00 -30.00   0.50    0.07    -- -104.50  61.00-179.00   76
 36  ω   -110.00 -51.00   0.50    0.07    -- -104.50 125.00 -90.00  118
 37  ω   -129.00-103.00   0.50    0.07    -- -104.50 150.00 139.79   52
 38  ω    -91.00 -51.00   0.50    0.07    -- -104.50 150.00 139.79   80
 39  ω    -94.00 -68.00   0.50    0.07    -- -104.50 125.00 150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2629446000
_diffrn_orient_matrix_UB_12      0.0244607000
_diffrn_orient_matrix_UB_13      -0.0217900000
_diffrn_orient_matrix_UB_21      0.0838861000
_diffrn_orient_matrix_UB_22      -0.0979159000
_diffrn_orient_matrix_UB_23      0.0556192000
_diffrn_orient_matrix_UB_31      -0.0177848000
_diffrn_orient_matrix_UB_32      -0.1001063000
_diffrn_orient_matrix_UB_33      -0.0596662000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1074
_reflns_number_total             1135
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0332
_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)+(0.0458P)²+0.4416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0900
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.c 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
O2 O 0.72900(15) 0.41871(8) 0.46887(4) 0.0322(3) Uani 1 1 d . . . . .
O1 O 0.34774(16) 0.40742(9) 0.43231(5) 0.0392(3) Uani 1 1 d . . . . .
H1 H 0.328254 0.460516 0.465317 0.059 Uiso 1 1 calc R U . . .
C1 C 0.750000 0.250000 0.25221(8) 0.0237(3) Uani 1 2 d S T P . .
C6 C 0.57759(19) 0.31243(10) 0.29451(6) 0.0232(3) Uani 1 1 d . . . . .
C3 C 0.9302(2) 0.17709(12) 0.14099(6) 0.0348(3) Uani 1 1 d . . . . .
H3 H 0.938378 0.172823 0.089058 0.042 Uiso 1 1 calc R U . . .
C2 C 0.750000 0.250000 0.17509(9) 0.0294(4) Uani 1 2 d S T P . .
C4 C 1.0920(2) 0.11296(12) 0.18267(7) 0.0342(3) Uani 1 1 d . . . . .
H4 H 1.208207 0.063372 0.158506 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4062(2) 0.38271(11) 0.26066(7) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.290102 0.427077 0.288216 0.034 Uiso 1 1 calc R U . . .
C7 C 0.62006(18) 0.27488(9) 0.37428(5) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.510508 0.204265 0.385531 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5738(2) 0.37443(10) 0.43010(6) 0.0226(3) Uani 1 1 d . . . . .


_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
O2 C8 1.2159(14) . ?
O1 H1 0.8400 . ?
O1 C8 1.3092(14) . ?
C1 C6 1.4056(14) . ?
C1 C6 1.4056(14) 2_655 ?
C1 C2 1.408(2) . ?
C6 C5 1.3684(16) . ?
C6 C7 1.5301(14) . ?
C3 H3 0.9500 . ?
C3 C2 1.4208(15) . ?
C3 C4 1.369(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.4241(17) 2_655 ?
C5 H5 0.9500 . ?
C7 C7 1.545(2) 2_655 ?
C7 H7 1.0000 . ?
C7 C8 1.5061(14) . ?

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
C8 O1 H1 109.5 . . ?
C6 C1 C6 113.37(14) . 2_655 ?
C6 C1 C2 123.32(7) . . ?
C6 C1 C2 123.32(7) 2_655 . ?
C1 C6 C7 106.80(9) . . ?
C5 C6 C1 119.76(11) . . ?
C5 C6 C7 133.27(10) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.24(11) . . ?
C1 C2 C3 115.98(8) . . ?
C1 C2 C3 115.98(8) . 2_655 ?
C3 C2 C3 128.03(16) 2_655 . ?
C3 C4 H4 118.5 . . ?
C3 C4 C5 122.92(11) . 2_655 ?
C5 C4 H4 118.5 2_655 . ?
C6 C5 C4 117.69(11) . 2_655 ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 2_655 . ?
C6 C7 C7 103.75(6) . 2_655 ?
C6 C7 H7 107.7 . . ?
C7 C7 H7 107.7 2_655 . ?
C8 C7 C6 115.27(9) . . ?
C8 C7 C7 114.23(8) . 2_655 ?
C8 C7 H7 107.7 . . ?
O2 C8 O1 123.92(10) . . ?
O2 C8 C7 123.68(10) . . ?
O1 C8 C7 112.40(9) . . ?

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
C1 C6 C5 C4 1.35(15) . . . 2_655 ?
C1 C6 C7 C7 19.44(12) . . . 2_655 ?
C1 C6 C7 C8 145.08(8) . . . . ?
C6 C1 C6 C5 176.48(12) 2_655 . . . ?
C6 C1 C6 C7 -7.70(5) 2_655 . . . ?
C6 C1 C2 C3 3.05(8) 2_655 . . . ?
C6 C1 C2 C3 3.05(7) . . . 2_655 ?
C6 C1 C2 C3 -176.95(8) 2_655 . . 2_655 ?
C6 C1 C2 C3 -176.95(8) . . . . ?
C6 C7 C8 O2 -115.33(12) . . . . ?
C6 C7 C8 O1 64.91(13) . . . . ?
C2 C1 C6 C5 -3.52(12) . . . . ?
C2 C1 C6 C7 172.30(5) . . . . ?
C2 C3 C4 C5 -1.47(18) . . . 2_655 ?
C4 C3 C2 C1 -0.56(13) . . . . ?
C4 C3 C2 C3 179.44(13) . . . 2_655 ?
C5 C6 C7 C7 -165.56(12) . . . 2_655 ?
C5 C6 C7 C8 -39.91(17) . . . . ?
C7 C6 C5 C4 -173.15(11) . . . 2_655 ?
C7 C7 C8 O2 4.72(15) 2_655 . . . ?
C7 C7 C8 O1 -175.04(10) 2_655 . . . ?

_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 1.633
_oxdiff_exptl_absorpt_empirical_full_min 0.662
