# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2330703'
loop_
_audit_author_name
_audit_author_address
'zhou jie'
;yunnan university
China
;
_audit_update_record             
;
2024-02-03 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-06-15
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.05500000000000001
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_weight         242.26
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.1343(4)
_cell_length_b                   9.3898(7)
_cell_length_c                   12.4989(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.387(2)
_cell_angle_gamma                90
_cell_volume                     592.70(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      77.19
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1204 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.8316.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.874
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            14995
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_theta_min         3.595
_diffrn_reflns_theta_max         77.313
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2439
_reflns_number_gt                2433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.978
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.1215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2439
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.14(14)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.6123(3) 0.63860(14) 0.24955(10) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.9068(3) 0.73571(15) 0.38321(11) 0.0238(3) Uani 1 1 d . . . . .
O3 O 0.3755(3) 0.61028(17) 0.62966(11) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.3051(4) 0.4571(2) 0.14840(14) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.4002(4) 0.4690(2) 0.05190(15) 0.0209(4) Uani 1 1 d . . . . .
H2 H 0.528216 0.539447 0.044094 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3059(4) 0.3761(2) -0.03408(15) 0.0241(4) Uani 1 1 d . . . . .
H3 H 0.374229 0.381605 -0.099716 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1131(4) 0.2761(2) -0.02368(16) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.046441 0.215119 -0.082938 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0168(4) 0.2648(2) 0.07320(16) 0.0223(4) Uani 1 1 d . . . . .
H5 H -0.116576 0.196764 0.079395 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1149(4) 0.35288(19) 0.16140(15) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.0312(4) 0.3362(2) 0.26753(16) 0.0200(4) Uani 1 1 d . . . . .
H7 H -0.126695 0.285074 0.271130 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1718(4) 0.3912(2) 0.35923(15) 0.0185(4) Uani 1 1 d . . . . .
H8 H 0.115329 0.380958 0.427150 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4216(3) 0.46950(19) 0.35009(14) 0.0156(3) Uani 1 1 d . . . . .
H9 H 0.559779 0.396351 0.344075 0.019 Uiso 1 1 calc R U . . .
C10 C 0.3742(3) 0.5534(2) 0.24482(14) 0.0172(4) Uani 1 1 d . . . . .
H10 H 0.221838 0.619388 0.245966 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5517(3) 0.58361(19) 0.42943(15) 0.0169(4) Uani 1 1 d . . . . .
H11 H 0.411219 0.649317 0.446239 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7151(4) 0.6620(2) 0.35677(15) 0.0182(4) Uani 1 1 d . . . . .
C13 C 0.7184(3) 0.5328(2) 0.53627(15) 0.0182(4) Uani 1 1 d . . . . .
H13A H 0.762140 0.431005 0.528809 0.022 Uiso 1 1 calc R U . . .
H13B H 0.886960 0.586644 0.549347 0.022 Uiso 1 1 calc R U . . .
C14 C 0.5858(4) 0.54969(19) 0.63435(16) 0.0186(4) Uani 1 1 d . . . . .
C15 C 0.7339(4) 0.4851(2) 0.73800(16) 0.0255(4) Uani 1 1 d . . . . .
H15A H 0.678217 0.531232 0.800520 0.038 Uiso 1 1 calc R U . . .
H15B H 0.924489 0.499076 0.741891 0.038 Uiso 1 1 calc R U . . .
H15C H 0.695191 0.382950 0.739029 0.038 Uiso 1 1 calc R U . . .


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 C10 1.453(2) . ?
O1 C12 1.367(2) . ?
O2 C12 1.200(2) . ?
O3 C14 1.213(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.412(3) . ?
C1 C10 1.497(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C6 C7 1.475(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.343(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.501(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.515(2) . ?
C9 C11 1.529(2) . ?
C10 H10 1.0000 . ?
C11 H11 1.0000 . ?
C11 C12 1.531(3) . ?
C11 C13 1.527(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.514(2) . ?
C14 C15 1.506(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C12 O1 C10 107.56(13) . . ?
C2 C1 C6 121.04(17) . . ?
C2 C1 C10 125.63(17) . . ?
C6 C1 C10 113.23(16) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.38(18) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.21(18) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.29(18) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.48(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 119.79(16) . . ?
C5 C6 C1 118.52(17) . . ?
C5 C6 C7 121.66(17) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.87(17) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 121.3 . . ?
C7 C8 C9 117.31(17) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 107.3 . . ?
C8 C9 C10 108.38(14) . . ?
C8 C9 C11 124.99(15) . . ?
C10 C9 H9 107.3 . . ?
C10 C9 C11 100.47(14) . . ?
C11 C9 H9 107.3 . . ?
O1 C10 C1 116.16(15) . . ?
O1 C10 C9 104.41(13) . . ?
O1 C10 H10 108.2 . . ?
C1 C10 C9 111.24(15) . . ?
C1 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C9 C11 H11 108.7 . . ?
C9 C11 C12 100.03(14) . . ?
C12 C11 H11 108.7 . . ?
C13 C11 C9 117.30(15) . . ?
C13 C11 H11 108.7 . . ?
C13 C11 C12 112.86(14) . . ?
O1 C12 C11 110.39(14) . . ?
O2 C12 O1 121.01(16) . . ?
O2 C12 C11 128.59(17) . . ?
C11 C13 H13A 108.7 . . ?
C11 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C11 114.35(15) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
O3 C14 C13 122.45(17) . . ?
O3 C14 C15 122.50(17) . . ?
C15 C14 C13 115.04(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 C2 C3 C4 2.0(3) . . . . ?
C1 C6 C7 C8 -16.4(3) . . . . ?
C2 C1 C6 C5 -2.3(3) . . . . ?
C2 C1 C6 C7 175.74(17) . . . . ?
C2 C1 C10 O1 -18.5(3) . . . . ?
C2 C1 C10 C9 -137.72(18) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 2.6(3) . . . . ?
C4 C5 C6 C7 -175.40(17) . . . . ?
C5 C6 C7 C8 161.56(19) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C1 C10 O1 165.04(14) . . . . ?
C6 C1 C10 C9 45.81(19) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C10 38.1(2) . . . . ?
C7 C8 C9 C11 155.93(17) . . . . ?
C8 C9 C10 O1 173.12(14) . . . . ?
C8 C9 C10 C1 -60.86(19) . . . . ?
C8 C9 C11 C12 -157.98(16) . . . . ?
C8 C9 C11 C13 79.7(2) . . . . ?
C9 C11 C12 O1 22.05(18) . . . . ?
C9 C11 C12 O2 -158.22(19) . . . . ?
C9 C11 C13 C14 -104.42(19) . . . . ?
C10 O1 C12 O2 -176.52(17) . . . . ?
C10 O1 C12 C11 3.23(19) . . . . ?
C10 C1 C2 C3 -176.19(18) . . . . ?
C10 C1 C6 C5 174.36(16) . . . . ?
C10 C1 C6 C7 -7.6(2) . . . . ?
C10 C9 C11 C12 -36.60(15) . . . . ?
C10 C9 C11 C13 -158.96(14) . . . . ?
C11 C9 C10 O1 40.60(15) . . . . ?
C11 C9 C10 C1 166.62(14) . . . . ?
C11 C13 C14 O3 -6.4(3) . . . . ?
C11 C13 C14 C15 173.38(16) . . . . ?
C12 O1 C10 C1 -150.78(16) . . . . ?
C12 O1 C10 C9 -27.91(17) . . . . ?
C12 C11 C13 C14 140.10(16) . . . . ?
C13 C11 C12 O1 147.50(15) . . . . ?
C13 C11 C12 O2 -32.8(3) . . . . ?

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2330704'
loop_
_audit_author_name
_audit_author_address
'zhou jie'
;yunnan university
China
;
_audit_update_record             
;
2024-02-03 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2024-02-03
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.05500000000000001
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_weight         242.26
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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
2.a Riding coordinates:
 C15(H15A,H15B,H15C)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P  21'
_space_group_name_Hall           'P 2yb'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4496(8)
_cell_length_b                   9.7142(15)
_cell_length_c                   11.8110(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.517(5)
_cell_angle_gamma                90
_cell_volume                     616.65(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298.15
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      8.88
_cell_measurement_theta_max      77.70
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5725
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1373 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.7592.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.930
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.15
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            14724
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_theta_min         8.878
_diffrn_reflns_theta_max         77.689
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2548
_reflns_number_gt                2492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.987
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.0354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2548
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.3476(2) 0.41963(14) 0.75986(11) 0.0553(3) Uani 1 1 d . . . . .
O2 O 0.1486(3) 0.25593(15) 0.64834(14) 0.0696(4) Uani 1 1 d . . . . .
O3 O 0.6441(3) 0.4051(2) 0.36908(13) 0.0778(5) Uani 1 1 d . . . . .
C1 C 0.6699(3) 0.5909(2) 0.84536(16) 0.0543(4) Uani 1 1 d . . . . .
C2 C 0.6232(4) 0.5803(3) 0.95672(18) 0.0710(5) Uani 1 1 d . . . . .
H2 H 0.492341 0.526459 0.972978 0.085 Uiso 1 1 calc R U . . .
C3 C 0.7742(6) 0.6512(4) 1.0440(2) 0.0910(8) Uani 1 1 d . . . . .
H3 H 0.744935 0.643605 1.119129 0.109 Uiso 1 1 calc R U . . .
C4 C 0.9652(6) 0.7319(3) 1.0207(2) 0.0940(9) Uani 1 1 d . . . . .
H4 H 1.063041 0.780082 1.079592 0.113 Uiso 1 1 calc R U . . .
C5 C 1.0132(5) 0.7422(3) 0.9094(2) 0.0792(7) Uani 1 1 d . . . . .
H5 H 1.144053 0.796883 0.894260 0.095 Uiso 1 1 calc R U . . .
C6 C 0.8675(3) 0.67141(19) 0.81985(18) 0.0586(4) Uani 1 1 d . . . . .
C7 C 0.9125(3) 0.6802(2) 0.70069(18) 0.0578(4) Uani 1 1 d . . . . .
H7 H 1.010687 0.751458 0.680427 0.069 Uiso 1 1 calc R U . . .
C8 C 0.8168(3) 0.5891(2) 0.62048(16) 0.0532(4) Uani 1 1 d . . . . .
H8 H 0.842115 0.597273 0.544809 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6668(3) 0.47329(17) 0.65793(14) 0.0466(3) Uani 1 1 d . . . . .
H9 H 0.783884 0.407627 0.700467 0.056 Uiso 1 1 calc R U . . .
C10 C 0.5110(3) 0.53186(18) 0.74124(14) 0.0472(4) Uani 1 1 d . . . . .
H10 H 0.408557 0.606280 0.702344 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3026(3) 0.34463(17) 0.66147(17) 0.0525(4) Uani 1 1 d . . . . .
C12 C 0.4731(3) 0.39034(17) 0.57786(15) 0.0491(4) Uani 1 1 d . . . . .
H12 H 0.552527 0.309393 0.550087 0.059 Uiso 1 1 calc R U . . .
C13 C 0.3282(3) 0.46812(18) 0.47586(14) 0.0492(4) Uani 1 1 d . . . . .
H13A H 0.162674 0.428969 0.457434 0.059 Uiso 1 1 calc R U . . .
H13B H 0.310525 0.563400 0.497725 0.059 Uiso 1 1 calc R U . . .
C14 C 0.4499(4) 0.4639(2) 0.37005(16) 0.0552(4) Uani 1 1 d . . . . .
C15 C 0.3122(5) 0.5358(3) 0.26577(18) 0.0713(5) Uani 1 1 d . . . . .
H15A H 0.401637 0.524648 0.202826 0.107 Uiso 1 1 d R U . . .
H15B H 0.297977 0.631968 0.282106 0.107 Uiso 1 1 d R U . . .
H15C H 0.149067 0.496558 0.245796 0.107 Uiso 1 1 d R U . . .


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 C10 1.447(2) . ?
O1 C11 1.359(2) . ?
O2 C11 1.195(2) . ?
O3 C14 1.204(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.403(3) . ?
C1 C10 1.496(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 C7 1.470(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.338(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.500(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.513(2) . ?
C9 C12 1.526(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.529(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.527(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.509(2) . ?
C14 C15 1.504(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C11 O1 C10 107.60(12) . . ?
C2 C1 C6 120.89(19) . . ?
C2 C1 C10 125.47(19) . . ?
C6 C1 C10 113.43(16) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 119.55(17) . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 122.2(2) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.16(17) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 121.5 . . ?
C7 C8 C9 117.08(16) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9 107.4 . . ?
C8 C9 C10 107.54(14) . . ?
C8 C9 C12 124.64(15) . . ?
C10 C9 H9 107.4 . . ?
C10 C9 C12 101.33(13) . . ?
C12 C9 H9 107.4 . . ?
O1 C10 C1 116.80(14) . . ?
O1 C10 C9 103.95(13) . . ?
O1 C10 H10 108.1 . . ?
C1 C10 C9 111.58(13) . . ?
C1 C10 H10 108.1 . . ?
C9 C10 H10 108.1 . . ?
O1 C11 C12 110.71(14) . . ?
O2 C11 O1 121.40(17) . . ?
O2 C11 C12 127.89(19) . . ?
C9 C12 C11 100.66(14) . . ?
C9 C12 H12 109.4 . . ?
C9 C12 C13 116.24(14) . . ?
C11 C12 H12 109.4 . . ?
C13 C12 C11 111.30(13) . . ?
C13 C12 H12 109.4 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.52(14) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
O3 C14 C13 121.89(17) . . ?
O3 C14 C15 122.19(18) . . ?
C15 C14 C13 115.92(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C9 15.24(17) . . . . ?
O1 C11 C12 C13 -108.57(16) . . . . ?
O2 C11 C12 C9 -164.35(18) . . . . ?
O2 C11 C12 C13 71.8(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C1 C6 C7 C8 -17.5(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C6 C7 179.86(18) . . . . ?
C2 C1 C10 O1 -21.5(3) . . . . ?
C2 C1 C10 C9 -140.90(19) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 179.8(2) . . . . ?
C5 C6 C7 C8 163.34(19) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C10 O1 163.78(14) . . . . ?
C6 C1 C10 C9 44.4(2) . . . . ?
C6 C7 C8 C9 -2.0(2) . . . . ?
C7 C8 C9 C10 39.9(2) . . . . ?
C7 C8 C9 C12 157.84(15) . . . . ?
C8 C9 C10 O1 171.97(13) . . . . ?
C8 C9 C10 C1 -61.31(17) . . . . ?
C8 C9 C12 C11 -153.24(15) . . . . ?
C8 C9 C12 C13 -32.9(2) . . . . ?
C9 C12 C13 C14 89.82(17) . . . . ?
C10 O1 C11 O2 -170.53(16) . . . . ?
C10 O1 C11 C12 9.85(18) . . . . ?
C10 C1 C2 C3 -174.0(2) . . . . ?
C10 C1 C6 C5 173.97(18) . . . . ?
C10 C1 C6 C7 -5.2(2) . . . . ?
C10 C9 C12 C11 -32.44(15) . . . . ?
C10 C9 C12 C13 87.89(15) . . . . ?
C11 O1 C10 C1 -154.81(14) . . . . ?
C11 O1 C10 C9 -31.43(16) . . . . ?
C11 C12 C13 C14 -155.75(15) . . . . ?
C12 C9 C10 O1 39.80(15) . . . . ?
C12 C9 C10 C1 166.52(14) . . . . ?
C12 C13 C14 O3 -0.7(3) . . . . ?
C12 C13 C14 C15 178.49(16) . . . . ?

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2341397'
loop_
_audit_author_name
_audit_author_address
'zhou jie'
;yunnan university
China
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H12 O2'
_chemical_formula_moiety         'C15 H12 O2'
_chemical_formula_weight         224.25
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_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:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0381(14)
_cell_length_b                   6.3338(6)
_cell_length_c                   15.2736(19)
_cell_angle_alpha                90
_cell_angle_beta                 108.132(4)
_cell_angle_gamma                90
_cell_volume                     1106.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    1111
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      26.38
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0859 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.9185.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.995
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            6394
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1953
_reflns_number_gt                1372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0819P)²+1.3542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1953
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1855
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.0379(2) 0.4523(4) 0.39103(19) 0.0349(7) Uani 1 1 d . . . . .
O2 O 0.1812(2) 0.2106(4) 0.42938(18) 0.0327(7) Uani 1 1 d . . . . .
C1 C -0.0213(3) 0.8103(6) 0.4105(3) 0.0373(10) Uani 1 1 d . . . . .
H1A H -0.097061 0.762379 0.414388 0.056 Uiso 1 1 calc R U . . .
H1B H -0.029344 0.953147 0.384658 0.056 Uiso 1 1 calc R U . . .
H1C H 0.035994 0.811229 0.472236 0.056 Uiso 1 1 calc R U . . .
C2 C 0.0189(3) 0.6642(5) 0.3499(3) 0.0322(9) Uani 1 1 d . . . . .
H2 H -0.041159 0.657521 0.287720 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1356(3) 0.7158(6) 0.3401(3) 0.0312(9) Uani 1 1 d . . . . .
H3 H 0.153839 0.845636 0.316596 0.037 Uiso 1 1 calc R U . . .
C4 C 0.2116(3) 0.5554(5) 0.3686(2) 0.0255(8) Uani 1 1 d . . . . .
C5 C 0.1491(3) 0.3853(5) 0.4006(2) 0.0260(8) Uani 1 1 d . . . . .
C6 C 0.3329(3) 0.5389(5) 0.3649(2) 0.0223(8) Uani 1 1 d . . . . .
C7 C 0.4018(3) 0.3650(5) 0.3958(2) 0.0235(8) Uani 1 1 d . . . . .
H7 H 0.371732 0.250872 0.421917 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5173(3) 0.3510(5) 0.3896(2) 0.0229(8) Uani 1 1 d . . . . .
C9 C 0.5608(3) 0.5212(5) 0.3485(2) 0.0236(8) Uani 1 1 d . . . . .
C10 C 0.4884(3) 0.6981(6) 0.3175(3) 0.0291(9) Uani 1 1 d . . . . .
H10 H 0.516452 0.813007 0.290312 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3791(3) 0.7080(6) 0.3255(2) 0.0268(8) Uani 1 1 d . . . . .
H11 H 0.332746 0.830174 0.304490 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6749(3) 0.5058(6) 0.3408(2) 0.0310(9) Uani 1 1 d . . . . .
H12 H 0.704591 0.618318 0.313451 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7426(3) 0.3321(6) 0.3719(3) 0.0322(9) Uani 1 1 d . . . . .
H13 H 0.818677 0.323614 0.365851 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6990(3) 0.1638(6) 0.4133(3) 0.0331(9) Uani 1 1 d . . . . .
H14 H 0.746398 0.043228 0.435423 0.040 Uiso 1 1 calc R U . . .
C15 C 0.5898(3) 0.1745(6) 0.4215(2) 0.0286(9) Uani 1 1 d . . . . .
H15 H 0.561841 0.060549 0.449253 0.034 Uiso 1 1 calc R U . . .


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 C2 1.469(4) . ?
O1 C5 1.368(4) . ?
O2 C5 1.208(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.491(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.495(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.346(5) . ?
C4 C5 1.482(5) . ?
C4 C6 1.483(5) . ?
C6 C7 1.371(5) . ?
C6 C11 1.423(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.425(5) . ?
C8 C9 1.427(5) . ?
C8 C15 1.408(5) . ?
C9 C10 1.408(5) . ?
C9 C12 1.418(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.360(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.364(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.421(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.361(5) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C2 110.3(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 109.8(3) . . ?
O1 C2 H2 109.7 . . ?
O1 C2 C3 102.5(3) . . ?
C1 C2 H2 109.7 . . ?
C1 C2 C3 115.1(3) . . ?
C3 C2 H2 109.7 . . ?
C2 C3 H3 124.2 . . ?
C4 C3 C2 111.6(3) . . ?
C4 C3 H3 124.2 . . ?
C3 C4 C5 106.9(3) . . ?
C3 C4 C6 128.3(3) . . ?
C5 C4 C6 124.7(3) . . ?
O1 C5 C4 108.6(3) . . ?
O2 C5 O1 121.0(3) . . ?
O2 C5 C4 130.3(3) . . ?
C7 C6 C4 122.7(3) . . ?
C7 C6 C11 118.4(3) . . ?
C11 C6 C4 118.8(3) . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.7(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 118.7(3) . . ?
C15 C8 C7 122.6(3) . . ?
C15 C8 C9 118.6(3) . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 C12 122.7(3) . . ?
C12 C9 C8 118.8(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C9 C12 H12 119.5 . . ?
C13 C12 C9 121.1(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C8 C15 H15 119.3 . . ?
C14 C15 C8 121.3(3) . . ?
C14 C15 H15 119.3 . . ?

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 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 C4 120.8(4) . . . . ?
C2 O1 C5 O2 -176.7(3) . . . . ?
C2 O1 C5 C4 1.8(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 C6 176.0(3) . . . . ?
C3 C4 C5 O1 -0.8(4) . . . . ?
C3 C4 C5 O2 177.6(4) . . . . ?
C3 C4 C6 C7 -179.5(4) . . . . ?
C3 C4 C6 C11 -1.1(5) . . . . ?
C4 C6 C7 C8 178.6(3) . . . . ?
C4 C6 C11 C10 -177.7(3) . . . . ?
C5 O1 C2 C1 -124.8(3) . . . . ?
C5 O1 C2 C3 -2.1(4) . . . . ?
C5 C4 C6 C7 -3.5(5) . . . . ?
C5 C4 C6 C11 174.9(3) . . . . ?
C6 C4 C5 O1 -177.5(3) . . . . ?
C6 C4 C5 O2 0.8(6) . . . . ?
C6 C7 C8 C9 -1.3(5) . . . . ?
C6 C7 C8 C15 179.6(3) . . . . ?
C7 C6 C11 C10 0.7(5) . . . . ?
C7 C8 C9 C10 1.3(5) . . . . ?
C7 C8 C9 C12 -178.8(3) . . . . ?
C7 C8 C15 C14 178.8(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C8 C9 C12 C13 0.0(5) . . . . ?
C9 C8 C15 C14 -0.3(5) . . . . ?
C9 C10 C11 C6 -0.6(6) . . . . ?
C9 C12 C13 C14 -0.4(6) . . . . ?
C10 C9 C12 C13 179.8(4) . . . . ?
C11 C6 C7 C8 0.3(5) . . . . ?
C12 C9 C10 C11 179.7(4) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C13 C14 C15 C8 -0.1(6) . . . . ?
C15 C8 C9 C10 -179.5(3) . . . . ?
C15 C8 C9 C12 0.4(5) . . . . ?

####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2505939'
loop_
_audit_author_name
_audit_author_address
'lifei gan'
;yunnan university
China
;
_audit_update_record             
;
2025-11-26 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2025-04-22
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.05500000000000001
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H13 N3 O4'
_chemical_formula_moiety         'C15 H13 N3 O4'
_chemical_formula_weight         299.28
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.6634(5)
_cell_length_b                   9.6041(8)
_cell_length_c                   25.492(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1386.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      6.95
_cell_measurement_theta_max      77.70
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1249 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.8764.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.893
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            22175
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_theta_min         4.921
_diffrn_reflns_theta_max         77.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2925
_reflns_number_gt                2909
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.998
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+0.2148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2925
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
N N 0.0311 0.0180 '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'

_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_
_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 0.1532(2) 0.66061(12) 0.47339(4) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.8846(2) 0.36441(12) 0.50519(4) 0.0217(2) Uani 1 1 d . . . . .
O3 O 0.8039(2) 0.31273(12) 0.42168(4) 0.0192(2) Uani 1 1 d . . . . .
O4 O 0.0325(2) 0.43020(14) 0.30278(5) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.3794(3) 0.61411(15) 0.35870(5) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.2408(3) 0.70667(16) 0.34548(6) 0.0313(3) Uani 1 1 d . . . . .
N3 N 0.1315(4) 0.7999(2) 0.33315(11) 0.0561(6) Uani 1 1 d . . . . .
C1 C 0.1082(3) 0.62726(18) 0.56560(6) 0.0248(3) Uani 1 1 d . . . . .
H1A H 0.221337 0.673476 0.588895 0.037 Uiso 1 1 calc R U . . .
H1B H 0.060780 0.537984 0.580961 0.037 Uiso 1 1 calc R U . . .
H1C H -0.031279 0.686533 0.561197 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2211(3) 0.60238(16) 0.51309(6) 0.0195(3) Uani 1 1 d . . . . .
C3 C 0.4234(3) 0.49944(16) 0.51328(6) 0.0196(3) Uani 1 1 d . . . . .
H3A H 0.361770 0.407721 0.524528 0.024 Uiso 1 1 calc R U . . .
H3B H 0.540133 0.529816 0.539833 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5511(3) 0.48071(16) 0.46105(6) 0.0180(3) Uani 1 1 d . . . . .
H4 H 0.609497 0.573611 0.448991 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7619(3) 0.38346(16) 0.46730(6) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.6324(3) 0.35950(16) 0.38324(6) 0.0177(3) Uani 1 1 d . . . . .
H6 H 0.700041 0.440433 0.363666 0.021 Uiso 1 1 calc R U . . .
C7 C 0.4226(3) 0.40979(16) 0.41536(6) 0.0170(3) Uani 1 1 d . . . . .
H7 H 0.337062 0.326539 0.429282 0.020 Uiso 1 1 calc R U . . .
C8 C 0.2588(3) 0.48710(16) 0.37842(6) 0.0197(3) Uani 1 1 d . . . . .
H8 H 0.110328 0.513394 0.397195 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1995(3) 0.39621(17) 0.33005(6) 0.0204(3) Uani 1 1 d . . . . .
C10 C 0.3483(3) 0.27262(17) 0.31797(6) 0.0194(3) Uani 1 1 d . . . . .
C11 C 0.5624(3) 0.24975(17) 0.34463(6) 0.0191(3) Uani 1 1 d . . . . .
C12 C 0.6983(3) 0.13336(17) 0.33318(6) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.843522 0.118552 0.350961 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6215(3) 0.03831(18) 0.29561(7) 0.0255(3) Uani 1 1 d . . . . .
H13 H 0.714269 -0.041574 0.287969 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4086(3) 0.05995(19) 0.26910(7) 0.0266(4) Uani 1 1 d . . . . .
H14 H 0.356037 -0.005608 0.243753 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2743(3) 0.1771(2) 0.27982(6) 0.0246(3) Uani 1 1 d . . . . .
H15 H 0.131353 0.192694 0.261228 0.030 Uiso 1 1 calc R U . . .


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 C2 1.219(2) . ?
O2 C5 1.2039(19) . ?
O3 C5 1.3677(19) . ?
O3 C6 1.4509(18) . ?
O4 C9 1.218(2) . ?
N1 N2 1.233(2) . ?
N1 C8 1.486(2) . ?
N2 N3 1.133(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.503(2) . ?
C2 C3 1.513(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.526(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.524(2) . ?
C4 C7 1.533(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.521(2) . ?
C6 C11 1.495(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.516(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.548(2) . ?
C9 C10 1.488(2) . ?
C10 C11 1.407(2) . ?
C10 C15 1.401(2) . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C6 107.71(11) . . ?
N2 N1 C8 113.07(14) . . ?
N3 N2 N1 173.5(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 122.17(15) . . ?
O1 C2 C3 122.79(14) . . ?
C1 C2 C3 115.04(13) . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C2 C3 C4 115.66(13) . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C3 C4 H4 108.7 . . ?
C3 C4 C5 110.63(12) . . ?
C3 C4 C7 119.37(13) . . ?
C5 C4 H4 108.7 . . ?
C5 C4 C7 100.31(12) . . ?
C7 C4 H4 108.7 . . ?
O2 C5 O3 120.44(14) . . ?
O2 C5 C4 128.98(14) . . ?
O3 C5 C4 110.58(12) . . ?
O3 C6 H6 108.7 . . ?
O3 C6 C7 104.92(11) . . ?
O3 C6 C11 113.79(13) . . ?
C7 C6 H6 108.7 . . ?
C11 C6 H6 108.7 . . ?
C11 C6 C7 111.78(12) . . ?
C4 C7 H7 108.4 . . ?
C6 C7 C4 100.33(12) . . ?
C6 C7 H7 108.4 . . ?
C8 C7 C4 123.00(13) . . ?
C8 C7 C6 107.40(12) . . ?
C8 C7 H7 108.4 . . ?
N1 C8 C7 109.33(13) . . ?
N1 C8 H8 109.9 . . ?
N1 C8 C9 107.05(12) . . ?
C7 C8 H8 109.9 . . ?
C7 C8 C9 110.58(13) . . ?
C9 C8 H8 109.9 . . ?
O4 C9 C8 118.16(15) . . ?
O4 C9 C10 122.37(15) . . ?
C10 C9 C8 119.46(13) . . ?
C11 C10 C9 120.84(14) . . ?
C15 C10 C9 119.77(14) . . ?
C15 C10 C11 119.39(15) . . ?
C10 C11 C6 115.85(14) . . ?
C12 C11 C6 124.01(14) . . ?
C12 C11 C10 120.11(15) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.98(15) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.28(16) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.94(16) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.30(16) . . ?
C14 C15 H15 119.9 . . ?

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
O1 C2 C3 C4 4.5(2) . . . . ?
O3 C6 C7 C4 38.93(14) . . . . ?
O3 C6 C7 C8 168.53(12) . . . . ?
O3 C6 C11 C10 160.32(13) . . . . ?
O3 C6 C11 C12 -21.9(2) . . . . ?
O4 C9 C10 C11 168.98(15) . . . . ?
O4 C9 C10 C15 -11.4(2) . . . . ?
N1 C8 C9 O4 -76.65(17) . . . . ?
N1 C8 C9 C10 102.52(15) . . . . ?
N2 N1 C8 C7 -154.39(14) . . . . ?
N2 N1 C8 C9 85.80(17) . . . . ?
C1 C2 C3 C4 -175.88(14) . . . . ?
C2 C3 C4 C5 175.64(12) . . . . ?
C2 C3 C4 C7 -68.81(18) . . . . ?
C3 C4 C5 O2 -29.9(2) . . . . ?
C3 C4 C5 O3 150.04(13) . . . . ?
C3 C4 C7 C6 -156.99(13) . . . . ?
C3 C4 C7 C8 84.27(19) . . . . ?
C4 C7 C8 N1 50.23(19) . . . . ?
C4 C7 C8 C9 167.85(13) . . . . ?
C5 O3 C6 C7 -25.73(15) . . . . ?
C5 O3 C6 C11 -148.22(13) . . . . ?
C5 C4 C7 C6 -36.11(13) . . . . ?
C5 C4 C7 C8 -154.85(14) . . . . ?
C6 O3 C5 O2 -178.77(14) . . . . ?
C6 O3 C5 C4 1.24(16) . . . . ?
C6 C7 C8 N1 -65.09(16) . . . . ?
C6 C7 C8 C9 52.54(16) . . . . ?
C6 C11 C12 C13 -178.36(15) . . . . ?
C7 C4 C5 O2 -156.90(16) . . . . ?
C7 C4 C5 O3 23.09(15) . . . . ?
C7 C6 C11 C10 41.68(18) . . . . ?
C7 C6 C11 C12 -140.51(14) . . . . ?
C7 C8 C9 O4 164.33(14) . . . . ?
C7 C8 C9 C10 -16.49(19) . . . . ?
C8 C9 C10 C11 -10.2(2) . . . . ?
C8 C9 C10 C15 169.45(14) . . . . ?
C9 C10 C11 C6 -2.6(2) . . . . ?
C9 C10 C11 C12 179.50(14) . . . . ?
C9 C10 C15 C14 -178.50(15) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C6 C7 C4 162.72(12) . . . . ?
C11 C6 C7 C8 -67.68(16) . . . . ?
C11 C10 C15 C14 1.1(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C10 -1.4(3) . . . . ?
C15 C10 C11 C6 177.81(14) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?

####################################################################### 
# 
# 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_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2333474'
loop_
_audit_author_name
_audit_author_address
'zhou jie'
;yunnan university
China
;
_audit_update_record             
;
2024-02-18 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-06-14
_diffrn_source_power             0.05500000000000001
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_weight         242.26
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_space_group_crystal_system      monoclinic
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C1(H1), C4(H4), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.3990(4)
_cell_length_b                   9.4977(8)
_cell_length_c                   11.7771(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.880(2)
_cell_angle_gamma                90
_cell_volume                     594.95(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    8864
_cell_measurement_theta_min      7.64
_cell_measurement_theta_max      77.26
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1145 before and 0.0375 after correction.
The Ratio of minimum to maximum transmission is 0.8166.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.875
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            9302
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_theta_min         7.636
_diffrn_reflns_theta_max         77.252
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2440
_reflns_number_gt                2431
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.983
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS V6.2.16/2021-10-22 && APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.0994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2440
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0734
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1108 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.6617(2) 0.58145(13) 0.23989(9) 0.0180(2) Uani 1 1 d . . . . .
O2 O 0.8631(2) 0.74875(13) 0.35392(11) 0.0225(3) Uani 1 1 d . . . . .
O3 O 0.3524(2) 0.59217(15) 0.62826(10) 0.0244(3) Uani 1 1 d . . . . .
C12 C 0.6791(3) 0.52867(17) 0.52445(13) 0.0161(3) Uani 1 1 d . . . . .
H12A H 0.696782 0.429453 0.501350 0.019 Uiso 1 1 calc R U . . .
H12B H 0.849908 0.569110 0.544854 0.019 Uiso 1 1 calc R U . . .
C7 C 0.4954(3) 0.46651(17) 0.25734(13) 0.0158(3) Uani 1 1 d . . . . .
H7 H 0.600114 0.388297 0.297096 0.019 Uiso 1 1 calc R U . . .
C6 C 0.3349(3) 0.40766(17) 0.15215(14) 0.0183(3) Uani 1 1 d . . . . .
C15 C 0.7070(3) 0.65741(17) 0.33936(14) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.1848(3) 0.40682(17) 0.37751(13) 0.0173(3) Uani 1 1 d . . . . .
H9 H 0.159229 0.397700 0.454989 0.021 Uiso 1 1 calc R U . . .
C13 C 0.5517(3) 0.53258(17) 0.62961(13) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.0876(3) 0.31412(18) 0.29616(14) 0.0194(3) Uani 1 1 d . . . . .
H10 H -0.013669 0.239408 0.316202 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5334(3) 0.61013(16) 0.42238(13) 0.0161(3) Uani 1 1 d . . . . .
H11 H 0.452213 0.694423 0.451252 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1329(3) 0.32453(17) 0.17648(14) 0.0196(3) Uani 1 1 d . . . . .
C14 C 0.6904(3) 0.4604(2) 0.73546(14) 0.0232(4) Uani 1 1 d . . . . .
H14A H 0.855443 0.504530 0.758441 0.035 Uiso 1 1 calc R U . . .
H14B H 0.712515 0.360567 0.718582 0.035 Uiso 1 1 calc R U . . .
H14C H 0.593570 0.468985 0.798300 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3824(3) 0.41889(19) 0.04056(15) 0.0233(4) Uani 1 1 d . . . . .
H1 H 0.517989 0.474999 0.024636 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3365(3) 0.52601(17) 0.34048(13) 0.0153(3) Uani 1 1 d . . . . .
H8 H 0.215951 0.594861 0.296884 0.018 Uiso 1 1 calc R U . . .
C4 C -0.0152(3) 0.25219(19) 0.08643(16) 0.0261(4) Uani 1 1 d . . . . .
H4 H -0.150193 0.195091 0.101699 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2290(4) 0.3470(2) -0.04825(16) 0.0301(4) Uani 1 1 d . . . . .
H2 H 0.259078 0.355622 -0.125092 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0329(4) 0.2629(2) -0.02539(16) 0.0306(4) Uani 1 1 d . . . . .
H3 H -0.068214 0.212857 -0.086160 0.037 Uiso 1 1 calc R U . . .


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 C7 1.4503(19) . ?
O1 C15 1.362(2) . ?
O2 C15 1.201(2) . ?
O3 C13 1.214(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.517(2) . ?
C12 C11 1.529(2) . ?
C7 H7 1.0000 . ?
C7 C6 1.493(2) . ?
C7 C8 1.517(2) . ?
C6 C5 1.415(2) . ?
C6 C1 1.386(2) . ?
C15 C11 1.533(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.340(2) . ?
C9 C8 1.505(2) . ?
C13 C14 1.505(2) . ?
C10 H10 0.9500 . ?
C10 C5 1.475(2) . ?
C11 H11 1.0000 . ?
C11 C8 1.532(2) . ?
C5 C4 1.395(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.396(3) . ?
C8 H8 1.0000 . ?
C4 H4 0.9500 . ?
C4 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C7 107.53(11) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C13 C12 C11 112.68(13) . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
O1 C7 H7 108.1 . . ?
O1 C7 C6 116.71(13) . . ?
O1 C7 C8 104.09(12) . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C8 111.28(13) . . ?
C8 C7 H7 108.1 . . ?
C5 C6 C7 113.49(14) . . ?
C1 C6 C7 125.63(15) . . ?
C1 C6 C5 120.63(16) . . ?
O1 C15 C11 110.74(13) . . ?
O2 C15 O1 121.58(15) . . ?
O2 C15 C11 127.68(15) . . ?
C10 C9 H9 121.5 . . ?
C10 C9 C8 116.93(14) . . ?
C8 C9 H9 121.5 . . ?
O3 C13 C12 121.74(15) . . ?
O3 C13 C14 122.51(14) . . ?
C14 C13 C12 115.74(14) . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C5 122.03(15) . . ?
C5 C10 H10 119.0 . . ?
C12 C11 C15 111.19(13) . . ?
C12 C11 H11 109.5 . . ?
C12 C11 C8 116.03(13) . . ?
C15 C11 H11 109.5 . . ?
C8 C11 C15 100.69(12) . . ?
C8 C11 H11 109.5 . . ?
C6 C5 C10 119.41(15) . . ?
C4 C5 C6 118.83(15) . . ?
C4 C5 C10 121.74(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C1 H1 120.3 . . ?
C6 C1 C2 119.37(17) . . ?
C2 C1 H1 120.3 . . ?
C7 C8 C11 101.08(12) . . ?
C7 C8 H8 107.6 . . ?
C9 C8 C7 107.63(13) . . ?
C9 C8 C11 124.27(13) . . ?
C9 C8 H8 107.6 . . ?
C11 C8 H8 107.6 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.56(17) . . ?
C3 C4 H4 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.66(17) . . ?
C3 C2 H2 119.7 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.93(17) . . ?
C2 C3 H3 120.0 . . ?

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 C7 C6 C5 -163.86(13) . . . . ?
O1 C7 C6 C1 21.8(2) . . . . ?
O1 C7 C8 C9 -171.58(12) . . . . ?
O1 C7 C8 C11 -39.94(14) . . . . ?
O1 C15 C11 C12 108.22(14) . . . . ?
O1 C15 C11 C8 -15.29(16) . . . . ?
O2 C15 C11 C12 -72.6(2) . . . . ?
O2 C15 C11 C8 163.94(16) . . . . ?
C12 C11 C8 C7 -87.61(15) . . . . ?
C12 C11 C8 C9 32.9(2) . . . . ?
C7 O1 C15 O2 170.83(14) . . . . ?
C7 O1 C15 C11 -9.89(16) . . . . ?
C7 C6 C5 C10 5.1(2) . . . . ?
C7 C6 C5 C4 -173.61(15) . . . . ?
C7 C6 C1 C2 173.81(16) . . . . ?
C6 C7 C8 C9 61.91(16) . . . . ?
C6 C7 C8 C11 -166.46(13) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C15 O1 C7 C6 154.64(13) . . . . ?
C15 O1 C7 C8 31.61(15) . . . . ?
C15 C11 C8 C7 32.50(14) . . . . ?
C15 C11 C8 C9 152.96(15) . . . . ?
C9 C10 C5 C6 17.8(2) . . . . ?
C9 C10 C5 C4 -163.52(16) . . . . ?
C13 C12 C11 C15 156.12(14) . . . . ?
C13 C12 C11 C8 -89.63(15) . . . . ?
C10 C9 C8 C7 -40.35(19) . . . . ?
C10 C9 C8 C11 -157.78(15) . . . . ?
C10 C5 C4 C3 -179.46(17) . . . . ?
C11 C12 C13 O3 1.7(2) . . . . ?
C11 C12 C13 C14 -177.21(14) . . . . ?
C5 C6 C1 C2 -0.1(2) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C1 C6 C5 C10 179.76(15) . . . . ?
C1 C6 C5 C4 1.0(2) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C8 C7 C6 C5 -44.63(18) . . . . ?
C8 C7 C6 C1 141.06(16) . . . . ?
C8 C9 C10 C5 2.0(2) . . . . ?

