# Supplementary Information (SI) for Chemical Science.
# 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_ccx-1_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2nfg2n
_database_code_depnum_ccdc_archive 'CCDC 2455791'
loop_
_audit_author_name
_audit_author_address
'chen chunxi'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2025-06-02 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_audit_creation_date             2024-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 O3'
_chemical_formula_sum            'C11 H10 O3'
_chemical_formula_weight         190.19
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2361(2)
_cell_length_b                   5.83641(11)
_cell_length_c                   13.4714(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.6635(17)
_cell_angle_gamma                90
_cell_volume                     955.55(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4083
_cell_measurement_temperature    298.41(10)
_cell_measurement_theta_max      72.7980
_cell_measurement_theta_min      5.1900
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.13
_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  0.0126
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5904
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.894
_diffrn_reflns_theta_min         4.623
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.41(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00 101.00   0.50    0.10    --   62.58  15.00 150.00   90
  2  ω     57.00  92.00   0.50    0.10    --   62.58  15.00  60.00   70
  3  ω     64.00 103.00   0.50    0.10    --   62.58  15.00   0.00   78
  4  ω     78.00 103.00   0.50    0.10    --   74.47  15.00  90.00   50
  5  ω     81.00 111.00   0.50    0.10    --   71.33  15.00   0.00   60
  6  ω     86.00 111.00   0.50    0.10    --   74.47  15.00 -30.00   50
  7  ω     55.00  86.00   0.50    0.10    --   62.58  15.00 -30.00   62
  8  ω     69.00  94.00   0.50    0.10    --   74.47  15.00  30.00   50
  9  ω     82.00 107.00   0.50    0.10    --   74.47  15.00  60.00   50
 10  ω     67.00  98.00   0.50    0.10    --   74.47  15.00 150.00   62
 11  ω     69.00  97.00   0.50    0.10    --   74.47  15.00 -60.00   56
 12  ω     56.00  99.00   0.50    0.10    --   62.58  15.00 -90.00   86
 13  ω     78.00 112.00   0.50    0.10    --   74.47  15.00-150.00   68
 14  ω     73.00  99.00   0.50    0.10    --   74.47  15.00-180.00   52
 15  ω     42.00  67.00   0.50    0.10    --   74.47-125.00 -90.00   50
 16  ω     27.00  56.00   0.50    0.10    --   62.58-125.00 -90.00   58
 17  ω     44.00  70.00   0.50    0.10    --   62.58-125.00-120.00   52
 18  ω     26.00  59.00   0.50    0.10    --   62.58-125.00-180.00   66
 19  ω     39.00  78.00   0.50    0.10    --   71.33-125.00-180.00   78
 20  ω     42.00  67.00   0.50    0.10    --   74.47-125.00-120.00   50
 21  ω     45.00  70.00   0.50    0.10    --   62.58-125.00  60.00   50
 22  ω     58.00  85.00   0.50    0.10    --   74.47-125.00 120.00   54
 23  ω     37.00  63.00   0.50    0.10    --   62.58-125.00 150.00   52
 24  ω     45.00  71.00   0.50    0.10    --   74.47-125.00 150.00   52
 25  ω     52.00  89.00   0.50    0.10    --   74.47-125.00-150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0878390000
_diffrn_orient_matrix_UB_12      0.0528451000
_diffrn_orient_matrix_UB_13      -0.0886342000
_diffrn_orient_matrix_UB_21      0.0814374000
_diffrn_orient_matrix_UB_22      -0.0707741000
_diffrn_orient_matrix_UB_23      -0.0735114000
_diffrn_orient_matrix_UB_31      -0.0415427000
_diffrn_orient_matrix_UB_32      -0.2486522000
_diffrn_orient_matrix_UB_33      0.0020683000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1600
_reflns_number_total             1834
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0350
_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)+(0.0562P)²+0.1026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C9(H9), C8(H8), C10(H10)
;
_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
O3 O 0.57553(7) -0.17803(17) -0.05809(8) 0.0740(3) Uani 1 1 d . . . . .
O1 O 0.90457(9) 0.21249(18) -0.06791(8) 0.0813(3) Uani 1 1 d . . . . .
C2 C 0.75806(9) -0.0520(2) -0.06562(8) 0.0554(3) Uani 1 1 d . . . . .
C7 C 0.83523(10) -0.0716(2) 0.15121(9) 0.0608(3) Uani 1 1 d . . . . .
H7 H 0.797353 -0.195590 0.120492 0.073 Uiso 1 1 calc R U . . .
C1 C 0.84709(10) 0.1029(2) -0.01758(10) 0.0573(3) Uani 1 1 d . . . . .
C11 C 0.92183(10) 0.2950(2) 0.14034(12) 0.0718(4) Uani 1 1 d . . . . .
H11 H 0.942646 0.417551 0.102628 0.086 Uiso 1 1 calc R U . . .
C6 C 0.86677(9) 0.1084(2) 0.09339(9) 0.0554(3) Uani 1 1 d . . . . .
C9 C 0.91526(14) 0.1150(3) 0.29954(13) 0.0892(5) Uani 1 1 d . . . . .
H9 H 0.932719 0.116680 0.368588 0.107 Uiso 1 1 calc R U . . .
C8 C 0.85965(12) -0.0682(3) 0.25409(11) 0.0763(4) Uani 1 1 d . . . . .
H8 H 0.838484 -0.189561 0.292309 0.092 Uiso 1 1 calc R U . . .
C3 C 0.64593(9) -0.0271(2) -0.03686(8) 0.0550(3) Uani 1 1 d . . . . .
C10 C 0.94537(13) 0.2971(3) 0.24297(15) 0.0904(5) Uani 1 1 d . . . . .
H10 H 0.981772 0.422057 0.274353 0.108 Uiso 1 1 calc R U . . .
C4 C 0.79235(12) -0.2930(2) -0.09235(10) 0.0683(4) Uani 1 1 d . . . . .
H4A H 0.869172 -0.334372 -0.076485 0.082 Uiso 1 1 calc R U . . .
H4B H 0.740734 -0.416588 -0.085581 0.082 Uiso 1 1 calc R U . . .
C5 C 0.76433(15) -0.1256(3) -0.17321(10) 0.0788(4) Uani 1 1 d . . . . .
H5A H 0.695594 -0.146919 -0.215861 0.095 Uiso 1 1 calc R U . . .
H5B H 0.824027 -0.064706 -0.206765 0.095 Uiso 1 1 calc R U . . .
O2 O 0.62592(7) 0.16010(16) 0.00800(7) 0.0702(3) Uani 1 1 d . . . . .
H2 H 0.5517(18) 0.161(4) 0.0309(15) 0.128(7) Uiso 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
O3 C3 1.2419(15) . ?
O1 C1 1.2141(15) . ?
C2 C1 1.5031(18) . ?
C2 C3 1.4755(16) . ?
C2 C4 1.5230(17) . ?
C2 C5 1.5221(17) . ?
C7 H7 0.9300 . ?
C7 C6 1.3893(17) . ?
C7 C8 1.3836(19) . ?
C1 C6 1.4867(18) . ?
C11 H11 0.9300 . ?
C11 C6 1.3928(18) . ?
C11 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.373(2) . ?
C9 C10 1.382(3) . ?
C8 H8 0.9300 . ?
C3 O2 1.2859(14) . ?
C10 H10 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.474(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O2 H2 0.99(2) . ?

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
C1 C2 C4 116.84(10) . . ?
C1 C2 C5 117.76(11) . . ?
C3 C2 C1 118.51(10) . . ?
C3 C2 C4 116.29(11) . . ?
C3 C2 C5 115.40(11) . . ?
C5 C2 C4 57.89(9) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.59(13) . . ?
O1 C1 C2 120.94(12) . . ?
O1 C1 C6 120.89(12) . . ?
C6 C1 C2 118.09(10) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C6 119.75(15) . . ?
C7 C6 C1 121.61(11) . . ?
C7 C6 C11 119.20(13) . . ?
C11 C6 C1 119.14(12) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.20(15) . . ?
C10 C9 H9 119.9 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.75(15) . . ?
C9 C8 H8 120.1 . . ?
O3 C3 C2 120.74(11) . . ?
O3 C3 O2 123.10(11) . . ?
O2 C3 C2 116.14(11) . . ?
C11 C10 C9 120.49(15) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C2 C4 H4A 117.7 . . ?
C2 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
C5 C4 C2 61.03(9) . . ?
C5 C4 H4A 117.7 . . ?
C5 C4 H4B 117.7 . . ?
C2 C5 H5A 117.7 . . ?
C2 C5 H5B 117.7 . . ?
C4 C5 C2 61.09(8) . . ?
C4 C5 H5A 117.7 . . ?
C4 C5 H5B 117.7 . . ?
H5A C5 H5B 114.8 . . ?
C3 O2 H2 112.4(13) . . ?

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 C1 C6 C7 -154.41(12) . . . . ?
O1 C1 C6 C11 23.17(17) . . . . ?
C2 C1 C6 C7 22.32(15) . . . . ?
C2 C1 C6 C11 -160.10(10) . . . . ?
C1 C2 C3 O3 -165.26(11) . . . . ?
C1 C2 C3 O2 16.66(15) . . . . ?
C1 C2 C4 C5 -107.38(13) . . . . ?
C1 C2 C5 C4 105.79(12) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C6 C11 C10 C9 0.4(2) . . . . ?
C8 C7 C6 C1 176.52(11) . . . . ?
C8 C7 C6 C11 -1.06(18) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C3 C2 C1 O1 -128.20(13) . . . . ?
C3 C2 C1 C6 55.07(14) . . . . ?
C3 C2 C4 C5 104.76(12) . . . . ?
C3 C2 C5 C4 -106.31(13) . . . . ?
C10 C11 C6 C7 0.78(18) . . . . ?
C10 C11 C6 C1 -176.86(11) . . . . ?
C10 C9 C8 C7 0.9(2) . . . . ?
C4 C2 C1 O1 84.67(14) . . . . ?
C4 C2 C1 C6 -92.06(13) . . . . ?
C4 C2 C3 O3 -17.95(16) . . . . ?
C4 C2 C3 O2 163.97(11) . . . . ?
C5 C2 C1 O1 18.68(17) . . . . ?
C5 C2 C1 C6 -158.04(11) . . . . ?
C5 C2 C3 O3 47.10(17) . . . . ?
C5 C2 C3 O2 -130.98(12) . . . . ?

_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.707
