# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 2253058'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 O4'
_chemical_formula_sum            'C20 H22 O4'
_chemical_formula_weight         326.38

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   11.519(3)
_cell_length_b                   12.304(3)
_cell_length_c                   12.831(3)
_cell_angle_alpha                111.475(3)
_cell_angle_beta                 92.051(3)
_cell_angle_gamma                101.680(3)
_cell_volume                     1645.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6199
_cell_measurement_theta_min      2.3465
_cell_measurement_theta_max      26.8436

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11736
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5729
_reflns_number_gt                4721
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0778P)²+0.2686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5729
_refine_ls_number_parameters     439
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.12506(14) 0.64114(13) 0.31657(12) 0.0293(3) Uani 1 1 d . . . . .
C2 C 0.12819(15) 0.74234(14) 0.41869(13) 0.0341(4) Uani 1 1 d . . . . .
C3 C 0.23254(17) 0.80535(15) 0.49599(14) 0.0417(4) Uani 1 1 d . . . . .
H3 H 0.303568 0.781114 0.480488 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2313(2) 0.90139(17) 0.59327(16) 0.0547(5) Uani 1 1 d . . . . .
H4 H 0.301291 0.941242 0.642331 0.066 Uiso 1 1 calc R U . . .
C5 C 0.1261(2) 0.94008(19) 0.61956(17) 0.0622(6) Uani 1 1 d . . . . .
H5 H 0.125808 1.004452 0.686251 0.075 Uiso 1 1 calc R U . . .
C6 C 0.0243(2) 0.88280(19) 0.54679(17) 0.0583(6) Uani 1 1 d . . . . .
H6 H -0.045243 0.909540 0.564004 0.070 Uiso 1 1 calc R U . . .
C7 C 0.02166(17) 0.78344(16) 0.44549(14) 0.0432(4) Uani 1 1 d . . . . .
C8 C -0.08373(18) 0.72373(19) 0.36958(16) 0.0503(5) Uani 1 1 d . . . . .
H8 H -0.153337 0.750558 0.386118 0.060 Uiso 1 1 calc R U . . .
C9 C -0.08569(16) 0.62798(17) 0.27294(15) 0.0430(4) Uani 1 1 d . . . . .
H9 H -0.156274 0.589334 0.224452 0.052 Uiso 1 1 calc R U . . .
C10 C 0.01908(14) 0.58752(14) 0.24645(12) 0.0311(4) Uani 1 1 d . . . . .
C11 C 0.10898(14) 0.44173(14) 0.10822(12) 0.0312(4) Uani 1 1 d . . . . .
C12 C 0.11668(15) 0.34102(14) 0.14796(13) 0.0350(4) Uani 1 1 d . . . . .
H12A H 0.177576 0.301687 0.111427 0.042 Uiso 1 1 calc R U . . .
H12B H 0.041043 0.282104 0.124206 0.042 Uiso 1 1 calc R U . . .
C13 C 0.14615(15) 0.38301(14) 0.27689(13) 0.0350(4) Uani 1 1 d . . . . .
H13 H 0.175215 0.318642 0.289290 0.042 Uiso 1 1 calc R U . . .
C14 C 0.25140(14) 0.49428(14) 0.32129(13) 0.0321(4) Uani 1 1 d . . . . .
C15 C 0.23361(13) 0.59332(13) 0.27895(12) 0.0288(3) Uani 1 1 d . . . . .
H15 H 0.304526 0.659923 0.307046 0.035 Uiso 1 1 calc R U . . .
C16 C 0.21979(14) 0.54214(14) 0.14994(13) 0.0321(4) Uani 1 1 d . . . . .
H16A H 0.212738 0.604293 0.122177 0.038 Uiso 1 1 calc R U . . .
H16B H 0.289134 0.512003 0.122983 0.038 Uiso 1 1 calc R U . . .
C17 C 0.03907(17) 0.39751(17) 0.34124(15) 0.0450(4) Uani 1 1 d . . . . .
H17 H 0.047569 0.467408 0.405109 0.054 Uiso 1 1 calc R U . . .
C18 C -0.0638(2) 0.3211(2) 0.3153(2) 0.0654(6) Uani 1 1 d . . . . .
H18A H -0.076246 0.249933 0.252105 0.078 Uiso 1 1 calc R U . . .
H18B H -0.124813 0.337476 0.359894 0.078 Uiso 1 1 calc R U . . .
C19 C 0.2894(2) 0.4741(2) 0.49846(17) 0.0683(7) Uani 1 1 d . U . . .
H19A H 0.216305 0.416841 0.491411 0.102 Uiso 1 1 calc R U . . .
H19B H 0.315481 0.522256 0.576783 0.102 Uiso 1 1 calc R U . . .
H19C H 0.349438 0.432568 0.465995 0.102 Uiso 1 1 calc R U . . .
C20 C 0.46293(17) 0.5352(2) 0.3081(2) 0.0619(6) Uani 1 1 d . . . . .
H20A H 0.466496 0.580746 0.261043 0.093 Uiso 1 1 calc R U . . .
H20B H 0.527233 0.494726 0.297037 0.093 Uiso 1 1 calc R U . . .
H20C H 0.469916 0.588209 0.385767 0.093 Uiso 1 1 calc R U . . .
C21 C 0.32709(14) 0.83958(13) 0.13609(13) 0.0305(3) Uani 1 1 d . . . . .
C22 C 0.43175(14) 0.79333(14) 0.13482(14) 0.0331(4) Uani 1 1 d . . . . .
C23 C 0.51864(16) 0.83270(16) 0.22999(15) 0.0413(4) Uani 1 1 d . . . . .
H23 H 0.507303 0.890113 0.297563 0.050 Uiso 1 1 calc R U . . .
C24 C 0.61881(17) 0.78806(18) 0.22456(18) 0.0518(5) Uani 1 1 d . . . . .
H24 H 0.674265 0.815527 0.288348 0.062 Uiso 1 1 calc R U . . .
C25 C 0.63901(18) 0.70144(19) 0.1241(2) 0.0575(5) Uani 1 1 d . . . . .
H25 H 0.708082 0.672728 0.120670 0.069 Uiso 1 1 calc R U . . .
C26 C 0.55654(18) 0.66000(18) 0.03188(18) 0.0534(5) Uani 1 1 d . . . . .
H26 H 0.569473 0.601593 -0.034276 0.064 Uiso 1 1 calc R U . . .
C27 C 0.45195(15) 0.70306(15) 0.03369(15) 0.0394(4) Uani 1 1 d . . . . .
C28 C 0.36558(17) 0.65974(16) -0.06227(15) 0.0447(4) Uani 1 1 d . . . . .
H28 H 0.377450 0.600295 -0.128189 0.054 Uiso 1 1 calc R U . . .
C29 C 0.26616(16) 0.70292(15) -0.06019(14) 0.0400(4) Uani 1 1 d . . . . .
H29 H 0.210590 0.673247 -0.124148 0.048 Uiso 1 1 calc R U . . .
C30 C 0.24711(14) 0.79322(14) 0.03947(13) 0.0320(4) Uani 1 1 d . . . . .
C31 C 0.10709(14) 0.91244(14) 0.12975(14) 0.0349(4) Uani 1 1 d . . . . .
C32 C 0.14662(15) 1.04011(15) 0.13556(15) 0.0394(4) Uani 1 1 d . . . . .
H32A H 0.112139 1.092352 0.196568 0.047 Uiso 1 1 calc R U . . .
H32B H 0.115575 1.043503 0.065820 0.047 Uiso 1 1 calc R U . . .
C33 C 0.28299(15) 1.08776(14) 0.15429(14) 0.0366(4) Uani 1 1 d . . . . .
H33 H 0.296663 1.175292 0.180403 0.044 Uiso 1 1 calc R U . . .
C34 C 0.33876(14) 1.06252(14) 0.25252(13) 0.0333(4) Uani 1 1 d . . . . .
C35 C 0.29454(14) 0.93069(14) 0.24032(13) 0.0313(4) Uani 1 1 d . . . . .
H35 H 0.328168 0.921643 0.307110 0.038 Uiso 1 1 calc R U . . .
C36 C 0.15850(14) 0.90035(15) 0.23387(13) 0.0347(4) Uani 1 1 d . . . . .
H36A H 0.130119 0.818978 0.229908 0.042 Uiso 1 1 calc R U . . .
H36B H 0.133437 0.954666 0.300662 0.042 Uiso 1 1 calc R U . . .
C37 C 0.34443(17) 1.04889(17) 0.04887(15) 0.0461(4) Uani 1 1 d . . . . .
H37 H 0.421141 1.038062 0.058274 0.055 Uiso 1 1 calc R U . . .
C38 C 0.3019(2) 1.0289(2) -0.05345(18) 0.0669(6) Uani 1 1 d . . . . .
H38A H 0.225588 1.038398 -0.067701 0.080 Uiso 1 1 calc R U . . .
H38B H 0.347772 1.005218 -0.112326 0.080 Uiso 1 1 calc R U . . .
C39 C 0.52538(19) 1.20637(18) 0.2808(2) 0.0602(6) Uani 1 1 d . . . . .
H39A H 0.511169 1.221742 0.213857 0.090 Uiso 1 1 calc R U . . .
H39B H 0.609549 1.216352 0.298291 0.090 Uiso 1 1 calc R U . . .
H39C H 0.496093 1.261687 0.342503 0.090 Uiso 1 1 calc R U . . .
C40 C 0.3425(2) 1.1393(2) 0.45536(16) 0.0590(6) Uani 1 1 d . . . . .
H40A H 0.290946 1.074893 0.468283 0.088 Uiso 1 1 calc R U . . .
H40B H 0.342332 1.214166 0.515323 0.088 Uiso 1 1 calc R U . . .
H40C H 0.422218 1.127120 0.453039 0.088 Uiso 1 1 calc R U . . .
O1 O 0.00551(9) 0.49021(10) 0.14524(9) 0.0346(3) Uani 1 1 d . . . . .
O2 O 0.08595(11) 0.38937(10) -0.01038(9) 0.0406(3) Uani 1 1 d . . . . .
H2 H 0.075932 0.440322 -0.034609 0.061 Uiso 1 1 calc R U . . .
O3 O 0.26990(11) 0.54991(10) 0.44053(9) 0.0410(3) Uani 1 1 d . . . . .
O4 O 0.35199(10) 0.44900(11) 0.27931(10) 0.0424(3) Uani 1 1 d . . . . .
O5 O 0.14407(10) 0.82973(10) 0.03011(9) 0.0365(3) Uani 1 1 d . . . . .
O6 O -0.01784(10) 0.88116(11) 0.11351(11) 0.0464(3) Uani 1 1 d . . . . .
H6A H -0.041162 0.808661 0.096738 0.070 Uiso 1 1 calc R U . . .
O7 O 0.46451(10) 1.08563(10) 0.26241(10) 0.0402(3) Uani 1 1 d . . . . .
O8 O 0.30089(11) 1.14211(10) 0.35062(10) 0.0435(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.377(2) . ?
C1 C2 1.433(2) . ?
C1 C15 1.509(2) . ?
C2 C3 1.416(2) . ?
C2 C7 1.426(2) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.412(3) . ?
C8 C9 1.358(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(2) . ?
C9 H9 0.9300 . ?
C10 O1 1.3841(18) . ?
C11 O2 1.4091(18) . ?
C11 O1 1.4570(19) . ?
C11 C16 1.507(2) . ?
C11 C12 1.519(2) . ?
C12 C13 1.543(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C17 1.513(3) . ?
C13 C14 1.542(2) . ?
C13 H13 0.9800 . ?
C14 O3 1.4161(19) . ?
C14 O4 1.4246(19) . ?
C14 C15 1.549(2) . ?
C15 C16 1.530(2) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.300(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?
C19 O3 1.433(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O4 1.423(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C30 1.378(2) . ?
C21 C22 1.432(2) . ?
C21 C35 1.515(2) . ?
C22 C23 1.418(2) . ?
C22 C27 1.429(2) . ?
C23 C24 1.368(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.403(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.358(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.409(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.417(3) . ?
C28 C29 1.354(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.413(2) . ?
C29 H29 0.9300 . ?
C30 O5 1.3675(19) . ?
C31 O6 1.3994(19) . ?
C31 O5 1.4538(19) . ?
C31 C36 1.511(2) . ?
C31 C32 1.517(2) . ?
C32 C33 1.538(2) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C37 1.514(3) . ?
C33 C34 1.551(2) . ?
C33 H33 0.9800 . ?
C34 O7 1.410(2) . ?
C34 O8 1.4295(19) . ?
C34 C35 1.546(2) . ?
C35 C36 1.527(2) . ?
C35 H35 0.9800 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.301(3) . ?
C37 H37 0.9300 . ?
C38 H38A 0.9300 . ?
C38 H38B 0.9300 . ?
C39 O7 1.437(2) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 O8 1.425(2) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
O2 H2 0.8200 . ?
O6 H6A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 118.69(14) . . ?
C10 C1 C15 117.95(13) . . ?
C2 C1 C15 123.30(13) . . ?
C3 C2 C7 117.27(15) . . ?
C3 C2 C1 123.45(15) . . ?
C7 C2 C1 119.28(15) . . ?
C4 C3 C2 121.49(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.86(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.44(18) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.81(18) . . ?
C8 C7 C2 118.81(16) . . ?
C6 C7 C2 119.38(17) . . ?
C9 C8 C7 121.43(16) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.81(16) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C1 C10 O1 123.89(14) . . ?
C1 C10 C9 121.98(15) . . ?
O1 C10 C9 114.14(14) . . ?
O2 C11 O1 104.97(11) . . ?
O2 C11 C16 112.93(13) . . ?
O1 C11 C16 109.06(12) . . ?
O2 C11 C12 106.74(12) . . ?
O1 C11 C12 110.86(13) . . ?
C16 C11 C12 112.05(13) . . ?
C11 C12 C13 113.96(12) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C17 C13 C14 113.89(14) . . ?
C17 C13 C12 114.14(14) . . ?
C14 C13 C12 110.28(13) . . ?
C17 C13 H13 105.9 . . ?
C14 C13 H13 105.9 . . ?
C12 C13 H13 105.9 . . ?
O3 C14 O4 110.53(12) . . ?
O3 C14 C13 113.19(13) . . ?
O4 C14 C13 104.15(12) . . ?
O3 C14 C15 105.77(12) . . ?
O4 C14 C15 110.82(13) . . ?
C13 C14 C15 112.50(12) . . ?
C1 C15 C16 108.04(12) . . ?
C1 C15 C14 113.31(13) . . ?
C16 C15 C14 109.11(12) . . ?
C1 C15 H15 108.8 . . ?
C16 C15 H15 108.8 . . ?
C14 C15 H15 108.8 . . ?
C11 C16 C15 108.05(13) . . ?
C11 C16 H16A 110.1 . . ?
C15 C16 H16A 110.1 . . ?
C11 C16 H16B 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C18 C17 C13 125.9(2) . . ?
C18 C17 H17 117.1 . . ?
C13 C17 H17 117.1 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C30 C21 C22 118.51(14) . . ?
C30 C21 C35 117.71(14) . . ?
C22 C21 C35 123.63(14) . . ?
C23 C22 C27 117.14(15) . . ?
C23 C22 C21 123.26(15) . . ?
C27 C22 C21 119.60(14) . . ?
C24 C23 C22 121.44(17) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 120.91(18) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 119.24(18) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 121.80(19) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C28 121.93(17) . . ?
C26 C27 C22 119.45(16) . . ?
C28 C27 C22 118.62(15) . . ?
C29 C28 C27 121.50(16) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 119.77(15) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
O5 C30 C21 124.05(14) . . ?
O5 C30 C29 113.96(13) . . ?
C21 C30 C29 121.99(15) . . ?
O6 C31 O5 105.35(12) . . ?
O6 C31 C36 112.83(14) . . ?
O5 C31 C36 109.54(12) . . ?
O6 C31 C32 107.68(13) . . ?
O5 C31 C32 110.12(14) . . ?
C36 C31 C32 111.14(13) . . ?
C31 C32 C33 113.70(13) . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32B 108.8 . . ?
C33 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C37 C33 C32 114.81(14) . . ?
C37 C33 C34 113.30(14) . . ?
C32 C33 C34 110.43(14) . . ?
C37 C33 H33 105.8 . . ?
C32 C33 H33 105.8 . . ?
C34 C33 H33 105.8 . . ?
O7 C34 O8 110.18(12) . . ?
O7 C34 C35 106.30(12) . . ?
O8 C34 C35 110.71(13) . . ?
O7 C34 C33 113.47(14) . . ?
O8 C34 C33 103.81(13) . . ?
C35 C34 C33 112.44(13) . . ?
C21 C35 C36 107.00(12) . . ?
C21 C35 C34 114.30(13) . . ?
C36 C35 C34 109.36(13) . . ?
C21 C35 H35 108.7 . . ?
C36 C35 H35 108.7 . . ?
C34 C35 H35 108.7 . . ?
C31 C36 C35 108.46(13) . . ?
C31 C36 H36A 110.0 . . ?
C35 C36 H36A 110.0 . . ?
C31 C36 H36B 110.0 . . ?
C35 C36 H36B 110.0 . . ?
H36A C36 H36B 108.4 . . ?
C38 C37 C33 127.25(19) . . ?
C38 C37 H37 116.4 . . ?
C33 C37 H37 116.4 . . ?
C37 C38 H38A 120.0 . . ?
C37 C38 H38B 120.0 . . ?
H38A C38 H38B 120.0 . . ?
O7 C39 H39A 109.5 . . ?
O7 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O7 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O8 C40 H40A 109.5 . . ?
O8 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O8 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C10 O1 C11 118.94(11) . . ?
C11 O2 H2 109.5 . . ?
C14 O3 C19 115.52(14) . . ?
C20 O4 C14 115.73(13) . . ?
C30 O5 C31 119.51(11) . . ?
C31 O6 H6A 109.5 . . ?
C34 O7 C39 115.84(14) . . ?
C40 O8 C34 115.74(13) . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_njg_auto
_database_code_depnum_ccdc_archive 'CCDC 2354975'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2024-06-07 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2024-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_chemical_absolute_configuration ab
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.62210(10)
_cell_length_b                   10.28440(10)
_cell_length_c                   13.4459(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1192.29(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9660
_cell_measurement_theta_min      4.2990
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10153
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.051
_diffrn_reflns_theta_min         5.415
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00   8.00   0.50    0.50    --   42.00 -77.00 150.00  106
  2  ω     59.00 131.00   0.50    0.50    --   42.00  77.00-180.00  144
  3  ω    -46.00   0.00   0.50    0.50    --   42.00 -82.00 -90.00   92
  4  ω     17.00 103.00   0.50    0.50    --   42.00  77.00  60.00  172
  5  ω     29.00  68.00   0.50    0.50    --   42.00 -82.00   0.00   78
  6  ω     16.00  47.00   0.50    0.50    --   42.00 -65.00-180.00   62
  7  ω     32.00  66.00   0.50    0.50    --   42.00 -43.00-180.00   68
  8  ω     30.00  67.00   0.50    0.50    --   42.00 -77.00 -60.00   74
  9  ω    -44.00   3.00   0.50    0.50    --   42.00 -65.00-180.00   94
 10  ω     16.00  62.00   0.50    0.50    --   42.00 -77.00 150.00   92
 11  ω     -7.00  18.00   0.50    0.50    --   42.00 -82.00  30.00   50
 12  ω    -42.00 -16.00   0.50    0.50    --   42.00 -82.00  30.00   52
 13  ω     30.00  60.00   0.50    0.50    --   42.00  77.00  90.00   60
 14  ω     18.00  62.00   0.50    0.50    --   42.00 -82.00 -90.00   88
 15  ω     80.00 131.00   0.50    0.50    --   42.00  77.00  90.00  102
 16  ω     42.00  69.00   0.50    0.50    --   42.00  65.00 -30.00   54
 17  ω    -14.00  11.00   0.50    0.50    --   42.00 -43.00-180.00   50
 18  ω     27.00  61.00   0.50    0.50    --   42.00 -82.00 120.00   68
 19  ω      4.00  63.00   0.50    0.50    --   93.40 -33.00 150.00  118
 20  ω     72.00  98.00   0.50    0.50    --   93.40 -82.00-120.00   52
 21  ω     43.00  69.00   0.50    0.50    --   93.40 -77.00  60.00   52
 22  ω     85.00 111.00   0.50    0.50    --   93.40 -82.00-180.00   52
 23  ω     45.00  70.00   0.50    0.50    --   93.40 -82.00-180.00   50
 24  ω     26.00  85.00   0.50    0.50    --   93.40 -82.00 -60.00  118
 25  ω     33.00 120.00   0.50    0.50    --   93.40 -82.00  30.00  174
 26  ω      4.00  56.00   0.50    0.50    --   93.40 -82.00-120.00  104
 27  ω      5.00  94.00   0.50    0.50    --   93.40 -59.00 -60.00  178
 28  ω     25.00  88.00   0.50    0.50    --   93.40 -82.00 120.00  126
 29  ω      4.00  97.00   0.50    0.50    --   93.40 -82.00 150.00  186
 30  ω     87.00 127.00   0.50    0.50    --   93.40 -33.00 150.00   80
 31  ω    135.00 181.00   0.50    0.50    --   93.40  42.00 120.00   92
 32  ω      8.00  88.00   0.50    0.50    --   93.40 -82.00  90.00  160
 33  ω     34.00 114.00   0.50    0.50    --   93.40 -82.00 -90.00  160
 34  ω    116.00 178.00   0.50    0.50    --   93.40  68.00 -60.00  124
 35  ω     70.00  95.00   0.50    0.50    --   93.40 -82.00 -30.00   50
 36  ω    149.00 183.00   0.50    0.50    --   93.40  42.00  30.00   68
 37  ω     77.00 133.00   0.50    0.50    --   93.40  42.00  30.00  112
 38  ω     75.00 119.00   0.50    0.50    --   93.40  42.00 120.00   88
 39  ω     34.00  77.00   0.50    0.50    --   93.40 -82.00-150.00   86
 40  ω     13.00 182.00   0.50    0.50    --   93.40   0.00   0.00  338
 41  ω      7.00  50.00   0.50    0.50    --   93.40 -50.00  30.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0106653000
_diffrn_orient_matrix_UB_12      -0.0117429000
_diffrn_orient_matrix_UB_13      -0.1140327000
_diffrn_orient_matrix_UB_21      -0.1424913000
_diffrn_orient_matrix_UB_22      0.0891995000
_diffrn_orient_matrix_UB_23      -0.0108565000
_diffrn_orient_matrix_UB_31      0.1071725000
_diffrn_orient_matrix_UB_32      0.1198096000
_diffrn_orient_matrix_UB_33      -0.0030625000
_diffrn_oxdiff_digest_frames     
;
01324e570271d4c5a5b4ea53dea6b620b0000302d1d
;
_diffrn_oxdiff_digest_hkl        
;
01479f47700e7c919b5ee489d3468bcfa68711
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2108
_reflns_number_total             2146
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.082
_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)+(0.0677P)²+0.1070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.77084(16) 0.40443(13) 0.67086(11) 0.0395(4) Uani 1 1 d . . . . .
O2 O 0.89411(17) 0.62816(16) 0.58714(12) 0.0472(4) Uani 1 1 d . . . . .
O3 O 0.4176(2) 0.50779(19) 0.82707(16) 0.0680(6) Uani 1 1 d . . . . .
C1 C 0.6545(2) 0.42239(18) 0.60211(14) 0.0316(4) Uani 1 1 d . . . . .
C2 C 0.6042(2) 0.3123(2) 0.55239(15) 0.0382(5) Uani 1 1 d . . . . .
H2 H 0.648941 0.232022 0.566107 0.046 Uiso 1 1 calc R . . . .
C3 C 0.4871(3) 0.3219(2) 0.48217(16) 0.0449(5) Uani 1 1 d . . . . .
H3 H 0.452146 0.247882 0.449398 0.054 Uiso 1 1 calc R . . . .
C4 C 0.4223(3) 0.4419(2) 0.46085(18) 0.0497(6) Uani 1 1 d . . . . .
H4 H 0.344340 0.448890 0.413369 0.060 Uiso 1 1 calc R . . . .
C5 C 0.4742(2) 0.5514(2) 0.51057(17) 0.0431(5) Uani 1 1 d . . . . .
H5 H 0.430355 0.631763 0.495813 0.052 Uiso 1 1 calc R . . . .
C6 C 0.5904(2) 0.54405(19) 0.58215(14) 0.0332(4) Uani 1 1 d . . . . .
C7 C 0.6400(2) 0.66103(18) 0.64151(15) 0.0371(4) Uani 1 1 d . . . . .
H7 H 0.635759 0.738437 0.599094 0.044 Uiso 1 1 calc R . . . .
C8 C 0.5268(3) 0.6779(2) 0.72908(18) 0.0485(5) Uani 1 1 d . . . . .
H8A H 0.554238 0.755034 0.766688 0.058 Uiso 1 1 calc R . . . .
H8B H 0.422171 0.689142 0.703920 0.058 Uiso 1 1 calc R . . . .
C9 C 0.5329(3) 0.5603(2) 0.79600(17) 0.0486(6) Uani 1 1 d . . . . .
C10 C 0.6928(3) 0.5137(2) 0.82284(17) 0.0480(5) Uani 1 1 d . . . . .
H10A H 0.684940 0.426581 0.850030 0.058 Uiso 1 1 calc R . . . .
H10B H 0.734260 0.569584 0.874497 0.058 Uiso 1 1 calc R . . . .
C11 C 0.8062(2) 0.5117(2) 0.73577(16) 0.0389(5) Uani 1 1 d . . . . .
H11 H 0.910640 0.498111 0.762578 0.047 Uiso 1 1 calc R . . . .
C12 C 0.8679(3) 0.7537(2) 0.73916(19) 0.0573(6) Uani 1 1 d . . . . .
H12A H 0.975643 0.739758 0.753541 0.086 Uiso 1 1 calc GR . . . .
H12B H 0.810739 0.759407 0.800295 0.086 Uiso 1 1 calc GR . . . .
H12C H 0.856045 0.833178 0.702490 0.086 Uiso 1 1 calc GR . . . .
C13 C 0.8063(2) 0.64079(19) 0.67761(15) 0.0393(5) Uani 1 1 d . . . . .
C14 C 1.0524(3) 0.5909(4) 0.5948(3) 0.0716(8) Uani 1 1 d . . . . .
H14A H 1.097010 0.585769 0.529441 0.107 Uiso 1 1 calc GR . . . .
H14B H 1.059471 0.507560 0.626578 0.107 Uiso 1 1 calc GR . . . .
H14C H 1.107780 0.654245 0.633377 0.107 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.377(2) . ?
O1 C11 1.439(3) . ?
O2 C13 1.439(3) . ?
O2 C14 1.422(3) . ?
O3 C9 1.206(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C6 C7 1.506(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.539(3) . ?
C7 C13 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.509(3) . ?
C9 C10 1.503(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.526(3) . ?
C11 H11 0.9800 . ?
C11 C13 1.541(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C13 1.522(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C1 O1 C11 117.31(15) . . ?
C14 O2 C13 118.0(2) . . ?
O1 C1 C2 116.28(16) . . ?
O1 C1 C6 122.57(17) . . ?
C2 C1 C6 121.14(18) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.93(19) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.67(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 120.20(17) . . ?
C5 C6 C1 117.86(19) . . ?
C5 C6 C7 121.82(17) . . ?
C6 C7 H7 109.3 . . ?
C6 C7 C8 108.41(16) . . ?
C6 C7 C13 109.01(16) . . ?
C8 C7 H7 109.3 . . ?
C13 C7 H7 109.3 . . ?
C13 C7 C8 111.56(18) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 110.09(16) . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
O3 C9 C8 122.4(2) . . ?
O3 C9 C10 122.0(2) . . ?
C10 C9 C8 115.5(2) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C9 C10 C11 114.07(18) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
O1 C11 C10 109.88(16) . . ?
O1 C11 H11 108.0 . . ?
O1 C11 C13 110.65(15) . . ?
C10 C11 H11 108.0 . . ?
C10 C11 C13 112.20(17) . . ?
C13 C11 H11 108.0 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
O2 C13 C7 103.75(16) . . ?
O2 C13 C11 110.58(17) . . ?
O2 C13 C12 110.19(17) . . ?
C7 C13 C11 106.15(16) . . ?
C12 C13 C7 113.35(19) . . ?
C12 C13 C11 112.44(17) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C1 C2 C3 179.83(17) . . . . ?
O1 C1 C6 C5 179.46(17) . . . . ?
O1 C1 C6 C7 -4.3(3) . . . . ?
O1 C11 C13 O2 -47.3(2) . . . . ?
O1 C11 C13 C7 64.6(2) . . . . ?
O1 C11 C13 C12 -170.90(19) . . . . ?
O3 C9 C10 C11 137.6(2) . . . . ?
C1 O1 C11 C10 82.4(2) . . . . ?
C1 O1 C11 C13 -42.0(2) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C6 C7 C8 -93.2(2) . . . . ?
C1 C6 C7 C13 28.4(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 176.24(17) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 -175.8(2) . . . . ?
C5 C6 C7 C8 82.8(2) . . . . ?
C5 C6 C7 C13 -155.54(18) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C7 C8 C9 61.7(2) . . . . ?
C6 C7 C13 O2 60.77(19) . . . . ?
C6 C7 C13 C11 -55.8(2) . . . . ?
C6 C7 C13 C12 -179.72(17) . . . . ?
C7 C8 C9 O3 -134.2(2) . . . . ?
C7 C8 C9 C10 46.6(3) . . . . ?
C8 C7 C13 O2 -179.54(15) . . . . ?
C8 C7 C13 C11 63.9(2) . . . . ?
C8 C7 C13 C12 -60.0(2) . . . . ?
C8 C9 C10 C11 -43.3(3) . . . . ?
C9 C10 C11 O1 -74.2(2) . . . . ?
C9 C10 C11 C13 49.4(2) . . . . ?
C10 C11 C13 O2 -170.39(17) . . . . ?
C10 C11 C13 C7 -58.5(2) . . . . ?
C10 C11 C13 C12 66.0(2) . . . . ?
C11 O1 C1 C2 -169.27(17) . . . . ?
C11 O1 C1 C6 11.3(3) . . . . ?
C13 C7 C8 C9 -58.4(2) . . . . ?
C14 O2 C13 C7 -171.8(2) . . . . ?
C14 O2 C13 C11 -58.4(3) . . . . ?
C14 O2 C13 C12 66.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.602
_oxdiff_exptl_absorpt_empirical_full_min 0.445
####################################################################### 
# 
# 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_nju_auto
_database_code_depnum_ccdc_archive 'CCDC 2361282'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2024-06-07 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2024-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C16 H20 O3'
_chemical_formula_sum            'C16 H20 O3'
_chemical_formula_weight         260.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   7.29259(12)
_cell_length_b                   11.7521(2)
_cell_length_c                   17.2208(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.2061(17)
_cell_angle_gamma                90
_cell_volume                     1447.74(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4759
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8080
_cell_measurement_theta_min      4.5750
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7333
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.078
_diffrn_reflns_theta_min         4.583
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 111.00   0.50    0.50    --   42.30  65.00-168.00  176
  2  ω     39.00  66.00   0.50    0.50    --   42.30 -65.00  55.00   54
  3  ω     71.00 135.00   0.50    0.54    --   93.40  65.00-168.00  128
  4  ω     27.00 115.00   0.50    0.54    --   93.40 -65.00  55.00  176
  5  ω     48.00  76.00   0.50    0.50    --   42.30  65.00  60.00   56
  6  ω     88.00 132.00   0.50    0.50    --   42.30  43.00 -60.00   88
  7  ω     15.00 115.00   0.50    0.50    --   42.30  82.00 -30.00  200
  8  ω     84.00 121.00   0.50    0.50    --   42.30  65.00  60.00   74
  9  ω     31.00  77.00   0.50    0.50    --   42.30  43.00 -60.00   92
 10  ω     98.00 124.00   0.50    0.50    --   42.30  65.00 120.00   52
 11  ω     19.00  59.00   0.50    0.50    --   42.30  65.00  90.00   80
 12  ω     21.00  93.00   0.50    0.50    --   42.30  65.00 120.00  144
 13  ω     65.00 132.00   0.50    0.54    --   93.40  42.00  90.00  134
 14  ω    150.00 176.00   0.50    0.54    --   93.40  68.00  90.00   52
 15  ω     94.00 120.00   0.50    0.54    --   93.40  68.00-120.00   52
 16  ω      6.00 108.00   0.50    0.54    --   93.40 -68.00 -60.00  204
 17  ω    121.00 171.00   0.50    0.54    --   93.40  42.00-180.00  100
 18  ω    145.00 170.00   0.50    0.54    --   93.40  42.00  90.00   50
 19  ω    103.00 129.00   0.50    0.54    --   93.40  77.00 120.00   52
 20  ω     63.00 102.00   0.50    0.54    --   93.40  42.00-180.00   78
 21  ω    157.00 182.00   0.50    0.54    --   93.40  77.00 120.00   50
 22  ω     96.00 175.00   0.50    0.54    --   93.40  77.00 150.00  158
 23  ω     84.00 138.00   0.50    0.54    --   93.40  68.00  90.00  108
 24  ω     74.00 165.00   0.50    0.54    --   93.40  68.00 120.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1912972000
_diffrn_orient_matrix_UB_12      -0.0534921000
_diffrn_orient_matrix_UB_13      0.0027725000
_diffrn_orient_matrix_UB_21      -0.0942654000
_diffrn_orient_matrix_UB_22      0.0814767000
_diffrn_orient_matrix_UB_23      -0.0659553000
_diffrn_orient_matrix_UB_31      0.0296808000
_diffrn_orient_matrix_UB_32      -0.0877560000
_diffrn_orient_matrix_UB_33      -0.0628893000
_diffrn_oxdiff_digest_frames     
;
016750e093789f3ed03dd6125d6dd605cc000306e13
;
_diffrn_oxdiff_digest_hkl        
;
01af5201195bcc378b3319ee4286d5d41cbd79
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed 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                2287
_reflns_number_total             2617
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.076
_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)+(0.0807P)²+0.1545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1343
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00B(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00E), C00D(H00F), C00E(H00G), C00F(H00H), C00H(H00L)
2.d Idealised Me refined as rotating group:
 C00G(H00I,H00J,H00K), C00J(H00O,H00P,H00Q)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O001 O 0.10719(12) 0.25418(8) 0.61629(6) 0.0490(3) Uani 1 1 d . . . . .
O002 O 0.63574(14) 0.05893(9) 0.60050(6) 0.0557(3) Uani 1 1 d . . . . .
O003 O 0.61755(17) 0.44919(12) 0.78163(7) 0.0710(4) Uani 1 1 d . . . . .
H003 H 0.684868 0.486368 0.816182 0.106 Uiso 1 1 calc GR . . . .
C004 C 0.27373(17) 0.32044(10) 0.61796(8) 0.0392(3) Uani 1 1 d . . . . .
C005 C 0.37956(18) 0.31014(11) 0.76875(8) 0.0428(3) Uani 1 1 d . . . . .
C006 C 0.50087(18) 0.11669(11) 0.60546(8) 0.0409(3) Uani 1 1 d . . . . .
C007 C 0.42138(17) 0.27716(11) 0.68895(8) 0.0408(3) Uani 1 1 d . . . . .
H007 H 0.540142 0.313480 0.684923 0.049 Uiso 1 1 calc R . . . .
C008 C 0.37568(19) 0.16386(12) 0.53372(8) 0.0439(3) Uani 1 1 d . . . . .
H00A H 0.255924 0.125275 0.526034 0.053 Uiso 1 1 calc R . . . .
H00B H 0.430290 0.149222 0.487633 0.053 Uiso 1 1 calc R . . . .
C009 C 0.34474(18) 0.29302(11) 0.54083(8) 0.0405(3) Uani 1 1 d . . . . .
H009 H 0.465961 0.330615 0.544150 0.049 Uiso 1 1 calc R . . . .
C00A C 0.48078(19) 0.39761(12) 0.81264(8) 0.0450(3) Uani 1 1 d . . . . .
C00B C 0.4508(2) 0.14761(13) 0.68319(8) 0.0472(4) Uani 1 1 d . . . . .
H00C H 0.549924 0.123382 0.726030 0.057 Uiso 1 1 calc R . . . .
H00D H 0.337162 0.108185 0.688723 0.057 Uiso 1 1 calc R . . . .
C00C C 0.4401(2) 0.43093(13) 0.88484(9) 0.0503(4) Uani 1 1 d . . . . .
H00E H 0.507810 0.489519 0.913357 0.060 Uiso 1 1 calc R . . . .
C00D C 0.2408(2) 0.25741(14) 0.80033(9) 0.0557(4) Uani 1 1 d . . . . .
H00F H 0.172973 0.198276 0.772514 0.067 Uiso 1 1 calc R . . . .
C00E C 0.2186(2) 0.33320(13) 0.46638(9) 0.0534(4) Uani 1 1 d . . . . .
H00G H 0.097503 0.304462 0.455398 0.064 Uiso 1 1 calc R . . . .
C00F C 0.3002(2) 0.37778(14) 0.91435(9) 0.0558(4) Uani 1 1 d . . . . .
H00H H 0.272912 0.400601 0.962550 0.067 Uiso 1 1 calc R . . . .
C00G C 0.2451(2) 0.44828(12) 0.62516(10) 0.0546(4) Uani 1 1 d . . . . .
H00I H 0.159299 0.475030 0.579301 0.082 Uiso 1 1 calc GR . . . .
H00J H 0.362707 0.486641 0.628978 0.082 Uiso 1 1 calc GR . . . .
H00K H 0.195147 0.463648 0.671723 0.082 Uiso 1 1 calc GR . . . .
C00H C 0.2007(3) 0.29062(16) 0.87227(10) 0.0639(5) Uani 1 1 d . . . . .
H00L H 0.106607 0.254104 0.892218 0.077 Uiso 1 1 calc R . . . .
C00I C 0.2648(4) 0.40471(18) 0.41617(12) 0.0763(6) Uani 1 1 d . . . . .
C00J C -0.0665(2) 0.3060(2) 0.61135(19) 0.1041(9) Uani 1 1 d . . . . .
H00O H -0.087285 0.358611 0.567876 0.156 Uiso 1 1 calc GR . . . .
H00P H -0.069163 0.346102 0.659687 0.156 Uiso 1 1 calc GR . . . .
H00Q H -0.162623 0.249030 0.603093 0.156 Uiso 1 1 calc GR . . . .
H00M H 0.174(4) 0.429(2) 0.3656(16) 0.116(8) Uiso 1 1 d . . . . .
H00N H 0.396(4) 0.434(2) 0.4250(15) 0.102(8) 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
O001 C004 1.4382(15) . ?
O001 C00J 1.393(2) . ?
O002 C006 1.2116(15) . ?
O003 H003 0.8200 . ?
O003 C00A 1.3619(17) . ?
C004 C007 1.5496(18) . ?
C004 C009 1.5504(18) . ?
C004 C00G 1.5253(19) . ?
C005 C007 1.5147(18) . ?
C005 C00A 1.3986(19) . ?
C005 C00D 1.3848(19) . ?
C006 C008 1.4928(18) . ?
C006 C00B 1.4992(19) . ?
C007 H007 0.9800 . ?
C007 C00B 1.5434(19) . ?
C008 H00A 0.9700 . ?
C008 H00B 0.9700 . ?
C008 C009 1.5430(19) . ?
C009 H009 0.9800 . ?
C009 C00E 1.5014(19) . ?
C00A C00C 1.390(2) . ?
C00B H00C 0.9700 . ?
C00B H00D 0.9700 . ?
C00C H00E 0.9300 . ?
C00C C00F 1.375(2) . ?
C00D H00F 0.9300 . ?
C00D C00H 1.383(2) . ?
C00E H00G 0.9300 . ?
C00E C00I 1.296(3) . ?
C00F H00H 0.9300 . ?
C00F C00H 1.377(2) . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?
C00G H00K 0.9600 . ?
C00H H00L 0.9300 . ?
C00I H00M 1.03(3) . ?
C00I H00N 1.00(3) . ?
C00J H00O 0.9600 . ?
C00J H00P 0.9600 . ?
C00J H00Q 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
C00J O001 C004 121.24(12) . . ?
C00A O003 H003 109.5 . . ?
O001 C004 C007 107.02(10) . . ?
O001 C004 C009 106.96(10) . . ?
O001 C004 C00G 113.98(11) . . ?
C007 C004 C009 108.13(10) . . ?
C00G C004 C007 110.14(11) . . ?
C00G C004 C009 110.38(11) . . ?
C00A C005 C007 120.01(12) . . ?
C00D C005 C007 122.22(12) . . ?
C00D C005 C00A 117.77(13) . . ?
O002 C006 C008 121.60(12) . . ?
O002 C006 C00B 122.73(12) . . ?
C008 C006 C00B 115.65(11) . . ?
C004 C007 H007 106.8 . . ?
C005 C007 C004 113.59(11) . . ?
C005 C007 H007 106.8 . . ?
C005 C007 C00B 111.45(11) . . ?
C00B C007 C004 110.91(10) . . ?
C00B C007 H007 106.8 . . ?
C006 C008 H00A 109.2 . . ?
C006 C008 H00B 109.2 . . ?
C006 C008 C009 112.02(11) . . ?
H00A C008 H00B 107.9 . . ?
C009 C008 H00A 109.2 . . ?
C009 C008 H00B 109.2 . . ?
C004 C009 H009 107.7 . . ?
C008 C009 C004 110.54(11) . . ?
C008 C009 H009 107.7 . . ?
C00E C009 C004 114.52(11) . . ?
C00E C009 C008 108.45(11) . . ?
C00E C009 H009 107.7 . . ?
O003 C00A C005 117.71(12) . . ?
O003 C00A C00C 121.70(13) . . ?
C00C C00A C005 120.58(13) . . ?
C006 C00B C007 110.95(11) . . ?
C006 C00B H00C 109.4 . . ?
C006 C00B H00D 109.4 . . ?
C007 C00B H00C 109.4 . . ?
C007 C00B H00D 109.4 . . ?
H00C C00B H00D 108.0 . . ?
C00A C00C H00E 119.8 . . ?
C00F C00C C00A 120.36(14) . . ?
C00F C00C H00E 119.8 . . ?
C005 C00D H00F 119.2 . . ?
C00H C00D C005 121.54(14) . . ?
C00H C00D H00F 119.2 . . ?
C009 C00E H00G 117.4 . . ?
C00I C00E C009 125.30(17) . . ?
C00I C00E H00G 117.4 . . ?
C00C C00F H00H 120.1 . . ?
C00C C00F C00H 119.76(14) . . ?
C00H C00F H00H 120.1 . . ?
C004 C00G H00I 109.5 . . ?
C004 C00G H00J 109.5 . . ?
C004 C00G H00K 109.5 . . ?
H00I C00G H00J 109.5 . . ?
H00I C00G H00K 109.5 . . ?
H00J C00G H00K 109.5 . . ?
C00D C00H H00L 120.0 . . ?
C00F C00H C00D 119.98(15) . . ?
C00F C00H H00L 120.0 . . ?
C00E C00I H00M 122.7(15) . . ?
C00E C00I H00N 119.2(15) . . ?
H00M C00I H00N 118(2) . . ?
O001 C00J H00O 109.5 . . ?
O001 C00J H00P 109.5 . . ?
O001 C00J H00Q 109.5 . . ?
H00O C00J H00P 109.5 . . ?
H00O C00J H00Q 109.5 . . ?
H00P C00J H00Q 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
O001 C004 C007 C005 -71.46(13) . . . . ?
O001 C004 C007 C00B 54.98(13) . . . . ?
O001 C004 C009 C008 -56.02(13) . . . . ?
O001 C004 C009 C00E 66.81(14) . . . . ?
O002 C006 C008 C009 -128.68(14) . . . . ?
O002 C006 C00B C007 128.45(14) . . . . ?
O003 C00A C00C C00F 179.51(14) . . . . ?
C004 C007 C00B C006 55.03(15) . . . . ?
C004 C009 C00E C00I 119.92(18) . . . . ?
C005 C007 C00B C006 -177.34(10) . . . . ?
C005 C00A C00C C00F 0.4(2) . . . . ?
C005 C00D C00H C00F -0.2(3) . . . . ?
C006 C008 C009 C004 -53.94(15) . . . . ?
C006 C008 C009 C00E 179.75(12) . . . . ?
C007 C004 C009 C008 58.93(13) . . . . ?
C007 C004 C009 C00E -178.24(11) . . . . ?
C007 C005 C00A O003 -1.1(2) . . . . ?
C007 C005 C00A C00C 178.09(13) . . . . ?
C007 C005 C00D C00H -178.16(15) . . . . ?
C008 C006 C00B C007 -50.27(16) . . . . ?
C008 C009 C00E C00I -116.12(18) . . . . ?
C009 C004 C007 C005 173.63(10) . . . . ?
C009 C004 C007 C00B -59.93(14) . . . . ?
C00A C005 C007 C004 -104.44(14) . . . . ?
C00A C005 C007 C00B 129.40(14) . . . . ?
C00A C005 C00D C00H 0.9(2) . . . . ?
C00A C00C C00F C00H 0.4(2) . . . . ?
C00B C006 C008 C009 50.06(17) . . . . ?
C00C C00F C00H C00D -0.5(3) . . . . ?
C00D C005 C007 C004 74.63(17) . . . . ?
C00D C005 C007 C00B -51.53(18) . . . . ?
C00D C005 C00A O003 179.83(14) . . . . ?
C00D C005 C00A C00C -1.0(2) . . . . ?
C00G C004 C007 C005 52.94(15) . . . . ?
C00G C004 C007 C00B 179.39(11) . . . . ?
C00G C004 C009 C008 179.47(11) . . . . ?
C00G C004 C009 C00E -57.69(15) . . . . ?
C00J O001 C004 C007 129.86(19) . . . . ?
C00J O001 C004 C009 -114.45(19) . . . . ?
C00J O001 C004 C00G 7.8(2) . . . . ?

_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 4.934
_oxdiff_exptl_absorpt_empirical_full_min 0.544
####################################################################### 
# 
# 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 2253059'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 Br O4'
_chemical_formula_sum            'C20 H22 Br O4'
_chemical_formula_weight         406.28

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.578(3)
_cell_length_b                   29.370(6)
_cell_length_c                   8.3953(17)
_cell_angle_alpha                90
_cell_angle_beta                 115.689(3)
_cell_angle_gamma                90
_cell_volume                     3683.7(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3300
_cell_measurement_theta_min      2.4873
_cell_measurement_theta_max      22.9381

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.253
_shelx_estimated_absorpt_T_min   0.714
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.763
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13302
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.387
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3239
_reflns_number_gt                2303
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0707P)²+1.3110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3239
_refine_ls_number_parameters     229
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.11935(3) 0.20807(2) 0.22451(7) 0.0725(2) Uani 1 1 d . . . . .
C1 C 0.0630(2) 0.36274(10) 0.0957(4) 0.0343(7) Uani 1 1 d . . . . .
C2 C -0.0036(2) 0.33134(11) -0.0094(4) 0.0380(8) Uani 1 1 d . . . . .
C3 C -0.0843(2) 0.34534(13) -0.1502(5) 0.0486(9) Uani 1 1 d . . . . .
H3 H -0.095013 0.376184 -0.175639 0.058 Uiso 1 1 calc R U . . .
C4 C -0.1467(3) 0.31423(15) -0.2495(6) 0.0646(12) Uani 1 1 d . . . . .
H4 H -0.198634 0.324000 -0.344655 0.078 Uiso 1 1 calc R U . . .
C5 C -0.1339(3) 0.26814(17) -0.2106(6) 0.0699(13) Uani 1 1 d . . . . .
H5 H -0.178070 0.247349 -0.276468 0.084 Uiso 1 1 calc R U . . .
C6 C -0.0561(3) 0.25324(13) -0.0751(6) 0.0593(11) Uani 1 1 d . . . . .
H6 H -0.047655 0.222240 -0.050916 0.071 Uiso 1 1 calc R U . . .
C7 C 0.0111(2) 0.28397(11) 0.0277(5) 0.0422(8) Uani 1 1 d . . . . .
C8 C 0.0940(3) 0.27086(12) 0.1664(5) 0.0474(9) Uani 1 1 d . . . . .
C9 C 0.1573(3) 0.30174(11) 0.2631(5) 0.0421(8) Uani 1 1 d . . . . .
H9 H 0.210844 0.291765 0.353539 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1428(2) 0.34903(11) 0.2278(4) 0.0357(8) Uani 1 1 d . . . . .
C11 C 0.2098(2) 0.38468(11) 0.3384(4) 0.0370(8) Uani 1 1 d . . . . .
H11 H 0.243168 0.372565 0.458031 0.044 Uiso 1 1 calc R U . . .
C12 C 0.1573(2) 0.42595(11) 0.3486(4) 0.0377(8) Uani 1 1 d . . . . .
H12A H 0.118322 0.417825 0.403046 0.045 Uiso 1 1 calc R U . . .
H12B H 0.197863 0.449669 0.418878 0.045 Uiso 1 1 calc R U . . .
C13 C 0.1028(2) 0.44246(10) 0.1622(4) 0.0336(7) Uani 1 1 d . . . . .
C14 C 0.1629(2) 0.45654(11) 0.0768(4) 0.0362(7) Uani 1 1 d . . . . .
H14A H 0.196474 0.483334 0.137226 0.043 Uiso 1 1 calc R U . . .
H14B H 0.125703 0.464984 -0.044957 0.043 Uiso 1 1 calc R U . . .
C15 C 0.2293(2) 0.41962(11) 0.0795(4) 0.0378(7) Uani 1 1 d . U . . .
H15 H 0.196197 0.395963 -0.006300 0.045 Uiso 1 1 calc R U . . .
C16 C 0.2771(2) 0.39748(11) 0.2645(4) 0.0381(8) Uani 1 1 d . . . . .
C17 C 0.2918(3) 0.44279(14) 0.0184(5) 0.0587(11) Uani 1 1 d D U . . .
H17A H 0.288810 0.475076 0.039561 0.070 Uiso 1 1 calc R U . . .
H17B H 0.351748 0.432974 0.097960 0.070 Uiso 1 1 calc DR U . . .
C18 C 0.2856(4) 0.4390(2) -0.1489(5) 0.0962(18) Uani 1 1 d D . . . .
H18A H 0.240764 0.421221 -0.232459 0.115 Uiso 1 1 calc R U . . .
H18B H 0.326294 0.454131 -0.179101 0.115 Uiso 1 1 calc R U . . .
C19 C 0.3902(3) 0.35725(16) 0.2075(7) 0.0782(15) Uani 1 1 d . . . . .
H19A H 0.365161 0.358722 0.080901 0.117 Uiso 1 1 calc R U . . .
H19B H 0.426023 0.330257 0.247989 0.117 Uiso 1 1 calc R U . . .
H19C H 0.426881 0.383577 0.257205 0.117 Uiso 1 1 calc DR U . . .
C20 C 0.3982(3) 0.41706(19) 0.5470(6) 0.0876(16) Uani 1 1 d . . . . .
H20A H 0.368769 0.421094 0.622441 0.131 Uiso 1 1 calc R U . . .
H20B H 0.451352 0.435410 0.589386 0.131 Uiso 1 1 calc R U . . .
H20C H 0.414024 0.385609 0.547280 0.131 Uiso 1 1 calc R U . . .
O1 O 0.04160(14) 0.40738(7) 0.0544(3) 0.0395(6) Uani 1 1 d D . . . .
O2 O 0.04878(14) 0.48056(7) 0.1586(3) 0.0430(6) Uani 1 1 d . . . . .
H2 H -0.003541 0.472465 0.122093 0.065 Uiso 1 1 calc DR U . . .
O3 O 0.31969(16) 0.35606(8) 0.2617(3) 0.0529(7) Uani 1 1 d . . . . .
O4 O 0.33928(15) 0.43058(9) 0.3708(3) 0.0554(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.907(4) . ?
C1 O1 1.363(3) . ?
C1 C10 1.368(4) . ?
C1 C2 1.415(5) . ?
C2 C3 1.409(5) . ?
C2 C7 1.424(4) . ?
C3 C4 1.361(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.416(5) . ?
C8 C9 1.359(5) . ?
C9 C10 1.419(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.516(4) . ?
C11 C12 1.515(4) . ?
C11 C16 1.541(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.508(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.426(4) . ?
C13 O1 1.454(4) . ?
C13 C14 1.516(4) . ?
C14 C15 1.538(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C17 1.504(5) . ?
C15 C16 1.548(4) . ?
C15 H15 0.9800 . ?
C16 O3 1.412(4) . ?
C16 O4 1.417(4) . ?
C17 C18 1.3675(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?
C19 O3 1.427(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O4 1.430(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O2 H2 0.8200 . ?

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
O1 C1 C10 122.9(3) . . ?
O1 C1 C2 114.9(3) . . ?
C10 C1 C2 122.2(3) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 C7 118.6(3) . . ?
C1 C2 C7 119.1(3) . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 124.0(3) . . ?
C6 C7 C2 118.6(3) . . ?
C8 C7 C2 117.3(3) . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 Br1 117.7(3) . . ?
C7 C8 Br1 120.1(3) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C1 C10 C9 118.3(3) . . ?
C1 C10 C11 119.2(3) . . ?
C9 C10 C11 122.4(3) . . ?
C10 C11 C12 107.5(3) . . ?
C10 C11 C16 112.8(3) . . ?
C12 C11 C16 111.2(3) . . ?
C10 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C16 C11 H11 108.4 . . ?
C13 C12 C11 107.4(3) . . ?
C13 C12 H12A 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
O2 C13 O1 106.3(2) . . ?
O2 C13 C12 111.3(3) . . ?
O1 C13 C12 111.1(2) . . ?
O2 C13 C14 108.2(2) . . ?
O1 C13 C14 108.9(3) . . ?
C12 C13 C14 110.9(3) . . ?
C13 C14 C15 114.5(3) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C17 C15 C14 105.7(3) . . ?
C17 C15 C16 113.8(3) . . ?
C14 C15 C16 111.3(3) . . ?
C17 C15 H15 108.6 . . ?
C14 C15 H15 108.6 . . ?
C16 C15 H15 108.6 . . ?
O3 C16 O4 111.7(3) . . ?
O3 C16 C11 104.5(3) . . ?
O4 C16 C11 111.7(3) . . ?
O3 C16 C15 112.8(3) . . ?
O4 C16 C15 105.1(3) . . ?
C11 C16 C15 111.2(2) . . ?
C18 C17 C15 123.9(4) . . ?
C18 C17 H17A 106.4 . . ?
C15 C17 H17A 106.4 . . ?
C18 C17 H17B 106.4 . . ?
C15 C17 H17B 106.4 . . ?
H17A C17 H17B 106.4 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 O1 C13 119.3(2) . . ?
C13 O2 H2 109.5 . . ?
C16 O3 C19 117.9(3) . . ?
C16 O4 C20 116.4(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 C1 C2 C3 2.3(5) . . . . ?
C10 C1 C2 C3 -177.3(3) . . . . ?
O1 C1 C2 C7 -177.8(3) . . . . ?
C10 C1 C2 C7 2.7(5) . . . . ?
C1 C2 C3 C4 179.6(4) . . . . ?
C7 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 2.3(6) . . . . ?
C3 C4 C5 C6 -2.6(7) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C5 C6 C7 C8 -178.3(4) . . . . ?
C5 C6 C7 C2 1.0(6) . . . . ?
C3 C2 C7 C6 -1.3(5) . . . . ?
C1 C2 C7 C6 178.8(3) . . . . ?
C3 C2 C7 C8 178.1(3) . . . . ?
C1 C2 C7 C8 -1.9(5) . . . . ?
C6 C7 C8 C9 -179.9(4) . . . . ?
C2 C7 C8 C9 0.8(5) . . . . ?
C6 C7 C8 Br1 -0.5(5) . . . . ?
C2 C7 C8 Br1 -179.8(2) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
Br1 C8 C9 C10 -179.7(2) . . . . ?
O1 C1 C10 C9 178.3(3) . . . . ?
C2 C1 C10 C9 -2.1(5) . . . . ?
O1 C1 C10 C11 2.2(5) . . . . ?
C2 C1 C10 C11 -178.2(3) . . . . ?
C8 C9 C10 C1 0.9(5) . . . . ?
C8 C9 C10 C11 176.9(3) . . . . ?
C1 C10 C11 C12 31.0(4) . . . . ?
C9 C10 C11 C12 -144.9(3) . . . . ?
C1 C10 C11 C16 -92.0(3) . . . . ?
C9 C10 C11 C16 92.1(4) . . . . ?
C10 C11 C12 C13 -60.1(3) . . . . ?
C16 C11 C12 C13 63.9(3) . . . . ?
C11 C12 C13 O2 178.1(2) . . . . ?
C11 C12 C13 O1 59.8(3) . . . . ?
C11 C12 C13 C14 -61.4(3) . . . . ?
O2 C13 C14 C15 176.9(3) . . . . ?
O1 C13 C14 C15 -68.0(3) . . . . ?
C12 C13 C14 C15 54.6(4) . . . . ?
C13 C14 C15 C17 -170.6(3) . . . . ?
C13 C14 C15 C16 -46.5(4) . . . . ?
C10 C11 C16 O3 -58.6(3) . . . . ?
C12 C11 C16 O3 -179.6(3) . . . . ?
C10 C11 C16 O4 -179.6(3) . . . . ?
C12 C11 C16 O4 59.5(3) . . . . ?
C10 C11 C16 C15 63.4(3) . . . . ?
C12 C11 C16 C15 -57.6(3) . . . . ?
C17 C15 C16 O3 -76.6(4) . . . . ?
C14 C15 C16 O3 164.1(3) . . . . ?
C17 C15 C16 O4 45.3(4) . . . . ?
C14 C15 C16 O4 -74.0(3) . . . . ?
C17 C15 C16 C11 166.3(3) . . . . ?
C14 C15 C16 C11 47.0(4) . . . . ?
C14 C15 C17 C18 -101.4(4) . . . . ?
C16 C15 C17 C18 136.3(4) . . . . ?
C10 C1 O1 C13 -4.6(4) . . . . ?
C2 C1 O1 C13 175.8(3) . . . . ?
O2 C13 O1 C1 -148.6(2) . . . . ?
C12 C13 O1 C1 -27.4(4) . . . . ?
C14 C13 O1 C1 95.0(3) . . . . ?
O4 C16 O3 C19 -55.8(4) . . . . ?
C11 C16 O3 C19 -176.7(3) . . . . ?
C15 C16 O3 C19 62.3(4) . . . . ?
O3 C16 O4 C20 -52.3(4) . . . . ?
C11 C16 O4 C20 64.4(4) . . . . ?
C15 C16 O4 C20 -174.9(3) . . . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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 2253062'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 Br O4'
_chemical_formula_sum            'C24 H23 Br O4'
_chemical_formula_weight         455.33

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.518(12)
_cell_length_b                   8.854(6)
_cell_length_c                   14.946(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.201(10)
_cell_angle_gamma                90
_cell_volume                     2051(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2986
_cell_measurement_theta_min      2.6279
_cell_measurement_theta_max      19.7254

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.032
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14342
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.314
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_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             3611
_reflns_number_gt                2197
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.1011P)²+0.2624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0072(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3611
_refine_ls_number_parameters     285
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1692
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.89337(5) 1.32820(7) -0.06169(5) 0.1076(4) Uani 1 1 d . . . . .
C1 C 0.6379(3) 0.7703(5) 0.0155(4) 0.0679(12) Uani 1 1 d D U . . .
C2 C 0.5859(3) 0.8918(5) -0.0305(4) 0.0697(12) Uani 1 1 d . U . . .
H2 H 0.526401 0.887491 -0.045257 0.084 Uiso 1 1 calc R U . . .
C3 C 0.6225(3) 1.0147(5) -0.0533(3) 0.0656(12) Uani 1 1 d . . . . .
H3 H 0.588050 1.095014 -0.084619 0.079 Uiso 1 1 calc R U . . .
C4 C 0.7136(3) 1.0232(4) -0.0298(3) 0.0556(10) Uani 1 1 d . . . . .
C5 C 0.7524(3) 1.1503(5) -0.0543(3) 0.0650(12) Uani 1 1 d . . . . .
H5 H 0.718455 1.230086 -0.087227 0.078 Uiso 1 1 calc R U . . .
C6 C 0.8404(4) 1.1567(5) -0.0296(3) 0.0730(13) Uani 1 1 d . . . . .
C7 C 0.8919(3) 1.0380(5) 0.0193(3) 0.0673(12) Uani 1 1 d . . . . .
H7 H 0.951551 1.044209 0.036442 0.081 Uiso 1 1 calc R U . . .
C8 C 0.8556(3) 0.9130(5) 0.0423(3) 0.0582(11) Uani 1 1 d . . . . .
H8 H 0.891020 0.834379 0.074611 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7650(2) 0.8992(4) 0.0181(3) 0.0516(10) Uani 1 1 d . . . . .
C10 C 0.7253(2) 0.7706(4) 0.0422(3) 0.0522(10) Uani 1 1 d . . . . .
C11 C 0.7750(3) 0.6331(4) 0.0913(3) 0.0575(11) Uani 1 1 d . . . . .
H11 H 0.826529 0.622248 0.073539 0.069 Uiso 1 1 calc R U . . .
C12 C 0.8028(2) 0.6384(4) 0.2013(3) 0.0530(10) Uani 1 1 d . . . . .
C13 C 0.7273(3) 0.6523(5) 0.2389(4) 0.0708(12) Uani 1 1 d . U . . .
H13 H 0.750810 0.620742 0.305785 0.085 Uiso 1 1 calc R U . . .
C14 C 0.6601(3) 0.5292(6) 0.1880(5) 0.0903(13) Uani 1 1 d . U . . .
H14A H 0.681713 0.432353 0.216626 0.108 Uiso 1 1 calc R U . . .
H14B H 0.607309 0.549646 0.200521 0.108 Uiso 1 1 calc R U . . .
C15 C 0.6380(3) 0.5153(5) 0.0822(5) 0.0932(14) Uani 1 1 d D U . . .
C16 C 0.7167(3) 0.4966(5) 0.0545(4) 0.0862(14) Uani 1 1 d . U . . .
H16A H 0.700100 0.489913 -0.014254 0.103 Uiso 1 1 calc R U . . .
H16B H 0.746987 0.404671 0.082184 0.103 Uiso 1 1 calc R U . . .
C17 C 0.6861(3) 0.8076(5) 0.2402(3) 0.0580(11) Uani 1 1 d . . . . .
C18 C 0.6182(3) 0.8134(6) 0.2748(4) 0.0800(15) Uani 1 1 d . . . . .
H18 H 0.599612 0.724760 0.294995 0.096 Uiso 1 1 calc R U . . .
C19 C 0.5778(3) 0.9476(8) 0.2800(4) 0.0915(16) Uani 1 1 d . U . . .
H19 H 0.531360 0.947463 0.301703 0.110 Uiso 1 1 calc R U . . .
C20 C 0.6042(3) 1.0779(7) 0.2542(4) 0.0829(15) Uani 1 1 d . U . . .
H20 H 0.576763 1.167846 0.258724 0.099 Uiso 1 1 calc R U . . .
C21 C 0.6725(3) 1.0786(5) 0.2210(3) 0.0774(14) Uani 1 1 d . . . . .
H21 H 0.690518 1.168698 0.201906 0.093 Uiso 1 1 calc R U . . .
C22 C 0.7142(3) 0.9440(5) 0.2161(3) 0.0637(11) Uani 1 1 d . . . . .
H22 H 0.761793 0.945576 0.196373 0.076 Uiso 1 1 calc R U . . .
C23 C 0.9005(3) 0.7788(7) 0.3314(3) 0.0787(14) Uani 1 1 d . . . . .
H23A H 0.928205 0.687942 0.362036 0.118 Uiso 1 1 calc R U . . .
H23B H 0.855645 0.806014 0.355465 0.118 Uiso 1 1 calc R U . . .
H23C H 0.942173 0.858868 0.344131 0.118 Uiso 1 1 calc R U . . .
C24 C 0.9149(3) 0.4516(6) 0.2218(4) 0.0841(15) Uani 1 1 d . U . . .
H24A H 0.944498 0.374493 0.266190 0.126 Uiso 1 1 calc R U . . .
H24B H 0.952683 0.536252 0.227507 0.126 Uiso 1 1 calc R U . . .
H24C H 0.897531 0.412289 0.158115 0.126 Uiso 1 1 calc R U . . .
O1 O 0.5913(5) 0.6367(8) 0.0127(9) 0.057(3) Uani 0.43(2) 1 d D U P A 1
O2 O 0.5878(4) 0.3970(6) 0.0231(7) 0.082(3) Uani 0.581(12) 1 d D U P A 1
H2A H 0.546668 0.393837 -0.030128 0.123 Uiso 0.581(12) 1 d R U P A 1
O3 O 0.84081(18) 0.4988(3) 0.2420(2) 0.0718(9) Uani 1 1 d . . . . .
O4 O 0.86411(16) 0.7544(3) 0.23086(18) 0.0539(7) Uani 1 1 d . . . . .
O1A O 0.5916(4) 0.6607(7) 0.0550(9) 0.063(3) Uani 0.57(2) 1 d D U P A 2
O2A O 0.5735(5) 0.4040(8) 0.0857(6) 0.060(3) Uani 0.419(12) 1 d D U P A 2
H2AA H 0.529730 0.365458 0.094521 0.089 Uiso 0.419(12) 1 d R U P A 2


_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
Br1 C6 1.895(5) . ?
C1 C10 1.359(6) . ?
C1 C2 1.400(6) . ?
C1 O1 1.404(7) . ?
C1 O1A 1.478(7) . ?
C2 C3 1.345(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.425(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(6) . ?
C4 C9 1.420(5) . ?
C5 C6 1.372(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(6) . ?
C7 C8 1.358(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.419(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(6) . ?
C10 C11 1.509(5) . ?
C11 C16 1.524(6) . ?
C11 C12 1.547(6) . ?
C11 H11 0.9800 . ?
C12 O4 1.402(5) . ?
C12 O3 1.424(4) . ?
C12 C13 1.540(6) . ?
C13 C17 1.537(6) . ?
C13 C14 1.555(7) . ?
C13 H13 0.9800 . ?
C14 C15 1.500(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O2 1.435(6) . ?
C15 O2A 1.466(8) . ?
C15 O1A 1.481(6) . ?
C15 C16 1.503(8) . ?
C15 O1 1.508(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.384(6) . ?
C17 C18 1.390(6) . ?
C18 C19 1.378(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.337(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.391(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O4 1.429(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O3 1.420(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O2 H2A 0.8501 . ?
O2A H2AA 0.8498 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 123.6(4) . . ?
C10 C1 O1 121.7(5) . . ?
C2 C1 O1 113.3(4) . . ?
C10 C1 O1A 121.9(4) . . ?
C2 C1 O1A 112.7(4) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C9 120.3(4) . . ?
C5 C4 C3 121.1(4) . . ?
C9 C4 C3 118.6(4) . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.6(4) . . ?
C5 C6 Br1 120.3(4) . . ?
C7 C6 Br1 119.1(4) . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.7(4) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 122.9(4) . . ?
C8 C9 C4 117.1(4) . . ?
C10 C9 C4 120.0(4) . . ?
C1 C10 C9 117.6(4) . . ?
C1 C10 C11 119.0(4) . . ?
C9 C10 C11 123.3(3) . . ?
C10 C11 C16 107.1(3) . . ?
C10 C11 C12 113.8(3) . . ?
C16 C11 C12 109.0(4) . . ?
C10 C11 H11 108.9 . . ?
C16 C11 H11 108.9 . . ?
C12 C11 H11 108.9 . . ?
O4 C12 O3 109.7(3) . . ?
O4 C12 C13 114.5(3) . . ?
O3 C12 C13 101.9(3) . . ?
O4 C12 C11 105.9(3) . . ?
O3 C12 C11 110.7(3) . . ?
C13 C12 C11 114.2(4) . . ?
C17 C13 C12 119.6(3) . . ?
C17 C13 C14 112.9(4) . . ?
C12 C13 C14 107.2(4) . . ?
C17 C13 H13 105.3 . . ?
C12 C13 H13 105.3 . . ?
C14 C13 H13 105.3 . . ?
C15 C14 C13 116.5(4) . . ?
C15 C14 H14A 108.2 . . ?
C13 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C13 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
O2A C15 O1A 106.3(5) . . ?
O2 C15 C14 125.9(6) . . ?
O2A C15 C14 86.1(5) . . ?
O1A C15 C14 97.6(6) . . ?
O2 C15 C16 97.0(5) . . ?
O2A C15 C16 130.1(5) . . ?
O1A C15 C16 115.8(5) . . ?
C14 C15 C16 112.3(4) . . ?
O2 C15 O1 92.7(5) . . ?
C14 C15 O1 123.2(7) . . ?
C16 C15 O1 100.0(6) . . ?
C15 C16 C11 108.2(4) . . ?
C15 C16 H16A 110.1 . . ?
C11 C16 H16A 110.1 . . ?
C15 C16 H16B 110.1 . . ?
C11 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C22 C17 C18 116.8(4) . . ?
C22 C17 C13 126.0(3) . . ?
C18 C17 C13 117.1(4) . . ?
C19 C18 C17 121.4(5) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 121.0(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.7(5) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 119.8(5) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 121.1(4) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 O1 C15 115.8(5) . . ?
C15 O2 H2A 134.8 . . ?
C24 O3 C12 116.7(3) . . ?
C12 O4 C23 116.0(3) . . ?
C1 O1A C15 113.0(5) . . ?
C15 O2A H2AA 160.7 . . ?

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
C10 C1 C2 C3 2.3(7) . . . . ?
O1 C1 C2 C3 -164.3(7) . . . . ?
O1A C1 C2 C3 166.9(6) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C3 C4 C5 179.3(4) . . . . ?
C2 C3 C4 C9 0.0(6) . . . . ?
C9 C4 C5 C6 -1.8(6) . . . . ?
C3 C4 C5 C6 178.9(4) . . . . ?
C4 C5 C6 C7 0.3(7) . . . . ?
C4 C5 C6 Br1 -179.7(3) . . . . ?
C5 C6 C7 C8 0.8(7) . . . . ?
Br1 C6 C7 C8 -179.2(3) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 C10 -179.2(4) . . . . ?
C7 C8 C9 C4 -1.0(6) . . . . ?
C5 C4 C9 C8 2.1(5) . . . . ?
C3 C4 C9 C8 -178.6(3) . . . . ?
C5 C4 C9 C10 -179.7(4) . . . . ?
C3 C4 C9 C10 -0.4(5) . . . . ?
C2 C1 C10 C9 -2.7(7) . . . . ?
O1 C1 C10 C9 162.8(7) . . . . ?
O1A C1 C10 C9 -165.9(6) . . . . ?
C2 C1 C10 C11 -179.9(4) . . . . ?
O1 C1 C10 C11 -14.4(9) . . . . ?
O1A C1 C10 C11 16.9(8) . . . . ?
C8 C9 C10 C1 179.8(4) . . . . ?
C4 C9 C10 C1 1.7(6) . . . . ?
C8 C9 C10 C11 -3.2(6) . . . . ?
C4 C9 C10 C11 178.8(3) . . . . ?
C1 C10 C11 C16 29.8(6) . . . . ?
C9 C10 C11 C16 -147.2(4) . . . . ?
C1 C10 C11 C12 -90.8(5) . . . . ?
C9 C10 C11 C12 92.2(5) . . . . ?
C10 C11 C12 O4 -67.5(4) . . . . ?
C16 C11 C12 O4 172.9(3) . . . . ?
C10 C11 C12 O3 173.6(3) . . . . ?
C16 C11 C12 O3 54.1(4) . . . . ?
C10 C11 C12 C13 59.4(4) . . . . ?
C16 C11 C12 C13 -60.2(4) . . . . ?
O4 C12 C13 C17 41.9(6) . . . . ?
O3 C12 C13 C17 160.2(4) . . . . ?
C11 C12 C13 C17 -80.4(5) . . . . ?
O4 C12 C13 C14 172.1(3) . . . . ?
O3 C12 C13 C14 -69.6(4) . . . . ?
C11 C12 C13 C14 49.7(4) . . . . ?
C17 C13 C14 C15 87.6(5) . . . . ?
C12 C13 C14 C15 -46.2(5) . . . . ?
C13 C14 C15 O2 170.5(5) . . . . ?
C13 C14 C15 O2A -174.8(5) . . . . ?
C13 C14 C15 O1A -68.9(5) . . . . ?
C13 C14 C15 C16 53.1(5) . . . . ?
C13 C14 C15 O1 -66.5(7) . . . . ?
O2 C15 C16 C11 167.8(5) . . . . ?
O2A C15 C16 C11 -163.2(6) . . . . ?
O1A C15 C16 C11 52.3(7) . . . . ?
C14 C15 C16 C11 -58.7(5) . . . . ?
O1 C15 C16 C11 73.7(6) . . . . ?
C10 C11 C16 C15 -62.2(5) . . . . ?
C12 C11 C16 C15 61.4(5) . . . . ?
C12 C13 C17 C22 -4.8(8) . . . . ?
C14 C13 C17 C22 -132.3(5) . . . . ?
C12 C13 C17 C18 180.0(5) . . . . ?
C14 C13 C17 C18 52.4(6) . . . . ?
C22 C17 C18 C19 3.5(7) . . . . ?
C13 C17 C18 C19 179.2(5) . . . . ?
C17 C18 C19 C20 -1.9(8) . . . . ?
C18 C19 C20 C21 0.7(8) . . . . ?
C19 C20 C21 C22 -1.1(7) . . . . ?
C18 C17 C22 C21 -3.9(7) . . . . ?
C13 C17 C22 C21 -179.2(5) . . . . ?
C20 C21 C22 C17 2.9(7) . . . . ?
C10 C1 O1 C15 29.2(13) . . . . ?
C2 C1 O1 C15 -163.9(7) . . . . ?
O2 C15 O1 C1 -153.9(10) . . . . ?
C14 C15 O1 C1 68.9(11) . . . . ?
C16 C15 O1 C1 -56.3(10) . . . . ?
O4 C12 O3 C24 -57.6(5) . . . . ?
C13 C12 O3 C24 -179.3(4) . . . . ?
C11 C12 O3 C24 58.9(5) . . . . ?
O3 C12 O4 C23 -59.5(4) . . . . ?
C13 C12 O4 C23 54.3(5) . . . . ?
C11 C12 O4 C23 -179.0(3) . . . . ?
C10 C1 O1A C15 -29.4(11) . . . . ?
C2 C1 O1A C15 165.8(6) . . . . ?
O2A C15 O1A C1 -159.7(8) . . . . ?
C14 C15 O1A C1 112.1(8) . . . . ?
C16 C15 O1A C1 -7.2(10) . . . . ?

_refine_diff_density_max         0.862
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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 2253061'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 O4'
_chemical_formula_sum            'C24 H24 O4'
_chemical_formula_weight         376.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_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                   7.029(2)
_cell_length_b                   24.045(7)
_cell_length_c                   11.708(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.515(4)
_cell_angle_gamma                90
_cell_volume                     1972.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4881
_cell_measurement_theta_min      2.4321
_cell_measurement_theta_max      26.0379

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14078
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.694
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_full        25.001
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3474
_reflns_number_gt                2771
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0612P)²+0.2779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3474
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2704(2) 0.28781(7) -0.01826(13) 0.0337(4) Uani 1 1 d . . . . .
C2 C 0.4331(2) 0.31184(7) 0.04053(15) 0.0413(4) Uani 1 1 d . . . . .
H2 H 0.549857 0.293663 0.040250 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4235(3) 0.36099(8) 0.09772(15) 0.0472(5) Uani 1 1 d . . . . .
H3 H 0.532346 0.375336 0.137434 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2492(3) 0.39030(7) 0.09707(15) 0.0434(4) Uani 1 1 d . . . . .
C5 C 0.2306(3) 0.44210(8) 0.15406(17) 0.0578(6) Uani 1 1 d . . . . .
H5 H 0.335417 0.456836 0.197175 0.069 Uiso 1 1 calc R U . . .
C6 C 0.0624(4) 0.47051(8) 0.14673(19) 0.0635(6) Uani 1 1 d . . . . .
H6 H 0.053668 0.504270 0.184730 0.076 Uiso 1 1 calc R U . . .
C7 C -0.0972(3) 0.44917(8) 0.08234(18) 0.0597(6) Uani 1 1 d . . . . .
H7 H -0.210617 0.469272 0.076277 0.072 Uiso 1 1 calc R U . . .
C8 C -0.0877(3) 0.39911(8) 0.02842(16) 0.0466(5) Uani 1 1 d . . . . .
H8 H -0.195471 0.385007 -0.012879 0.056 Uiso 1 1 calc R U . . .
C9 C 0.0838(2) 0.36850(7) 0.03463(14) 0.0387(4) Uani 1 1 d . . . . .
C10 C 0.1000(2) 0.31609(7) -0.02077(13) 0.0334(4) Uani 1 1 d . . . . .
C11 C 0.2787(2) 0.23415(7) -0.08461(13) 0.0327(4) Uani 1 1 d . . . . .
H11A H 0.405968 0.230563 -0.112519 0.039 Uiso 1 1 calc R U . . .
C12 C 0.1313(2) 0.23812(7) -0.18802(14) 0.0372(4) Uani 1 1 d . . . . .
H12A H 0.160910 0.269307 -0.236091 0.045 Uiso 1 1 d R U . . .
H12B H 0.133200 0.204387 -0.233361 0.045 Uiso 1 1 d R U . . .
C13 C -0.0635(2) 0.24598(7) -0.14349(14) 0.0348(4) Uani 1 1 d . . . . .
C14 C -0.1139(2) 0.19781(7) -0.06873(13) 0.0344(4) Uani 1 1 d . . . . .
H14A H -0.131819 0.164882 -0.116193 0.041 Uiso 1 1 d R U . . .
H14B H -0.234519 0.205832 -0.037243 0.041 Uiso 1 1 d R U . . .
C15 C 0.0359(2) 0.18493(6) 0.03064(13) 0.0306(4) Uani 1 1 d . . . . .
H15A H 0.037099 0.216746 0.083020 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2376(2) 0.18157(6) -0.01385(13) 0.0310(4) Uani 1 1 d . . . . .
C17 C -0.0230(2) 0.13465(7) 0.09765(13) 0.0335(4) Uani 1 1 d . . . . .
C18 C -0.0749(2) 0.08478(7) 0.04383(16) 0.0442(4) Uani 1 1 d . . . . .
H18 H -0.071975 0.081750 -0.035207 0.053 Uiso 1 1 calc R U . . .
C19 C -0.1309(3) 0.03946(8) 0.1064(2) 0.0584(6) Uani 1 1 d . . . . .
H19 H -0.165333 0.006358 0.069248 0.070 Uiso 1 1 calc R U . . .
C20 C -0.1356(3) 0.04342(9) 0.2235(2) 0.0628(6) Uani 1 1 d . . . . .
H20 H -0.171587 0.012859 0.265483 0.075 Uiso 1 1 calc R U . . .
C21 C -0.0871(3) 0.09248(10) 0.27826(18) 0.0585(6) Uani 1 1 d . . . . .
H21 H -0.091749 0.095272 0.357221 0.070 Uiso 1 1 calc R U . . .
C22 C -0.0311(2) 0.13793(8) 0.21594(14) 0.0419(4) Uani 1 1 d . . . . .
H22 H 0.001451 0.171021 0.253685 0.050 Uiso 1 1 calc R U . . .
C23 C 0.4092(3) 0.12174(9) -0.13770(19) 0.0569(5) Uani 1 1 d . . . . .
H23A H 0.519347 0.126666 -0.084795 0.085 Uiso 1 1 calc R U . . .
H23B H 0.416009 0.146869 -0.200956 0.085 Uiso 1 1 calc R U . . .
H23C H 0.405521 0.084150 -0.165435 0.085 Uiso 1 1 calc R U . . .
C24 C 0.4244(3) 0.12915(7) 0.13777(17) 0.0481(5) Uani 1 1 d . . . . .
H24A H 0.388385 0.132313 0.214923 0.072 Uiso 1 1 calc R U . . .
H24B H 0.558181 0.120978 0.138916 0.072 Uiso 1 1 calc R U . . .
H24C H 0.352650 0.099753 0.099216 0.072 Uiso 1 1 calc R U . . .
O1 O -0.06678(15) 0.29734(5) -0.07667(10) 0.0388(3) Uani 1 1 d . . . . .
O2 O -0.21224(16) 0.25141(5) -0.22890(10) 0.0450(3) Uani 1 1 d . . . . .
H2A H -0.172992 0.267107 -0.284612 0.068 Uiso 1 1 calc R U . . .
O3 O 0.23964(15) 0.13299(5) -0.08070(10) 0.0394(3) Uani 1 1 d . . . . .
O4 O 0.38504(15) 0.18086(5) 0.07804(10) 0.0385(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.376(2) . ?
C1 C2 1.411(2) . ?
C1 C11 1.510(2) . ?
C2 C3 1.363(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.423(2) . ?
C4 C5 1.424(3) . ?
C5 C6 1.362(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.363(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.409(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.426(2) . ?
C10 O1 1.3726(19) . ?
C11 C12 1.533(2) . ?
C11 C16 1.551(2) . ?
C11 H11A 0.9800 . ?
C12 C13 1.515(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.3947(19) . ?
C13 O1 1.4632(19) . ?
C13 C14 1.510(2) . ?
C14 C15 1.538(2) . ?
C14 H14A 0.9698 . ?
C14 H14B 0.9701 . ?
C15 C17 1.517(2) . ?
C15 C16 1.550(2) . ?
C15 H15A 0.9800 . ?
C16 O3 1.4066(18) . ?
C16 O4 1.4340(18) . ?
C17 C18 1.390(2) . ?
C17 C22 1.393(2) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O3 1.437(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O4 1.442(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O2 H2A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 118.61(15) . . ?
C10 C1 C11 118.69(14) . . ?
C2 C1 C11 122.58(14) . . ?
C3 C2 C1 121.68(17) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.44(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C9 119.45(16) . . ?
C3 C4 C5 123.06(17) . . ?
C9 C4 C5 117.48(18) . . ?
C6 C5 C4 121.37(19) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.34(19) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.67(19) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.65(17) . . ?
C8 C9 C10 122.43(16) . . ?
C4 C9 C10 117.92(16) . . ?
O1 C10 C1 123.86(14) . . ?
O1 C10 C9 114.31(14) . . ?
C1 C10 C9 121.82(14) . . ?
C1 C11 C12 107.59(13) . . ?
C1 C11 C16 113.93(13) . . ?
C12 C11 C16 109.26(13) . . ?
C1 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C16 C11 H11A 108.7 . . ?
C13 C12 C11 107.99(13) . . ?
C13 C12 H12A 110.1 . . ?
C11 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
O2 C13 O1 105.18(12) . . ?
O2 C13 C14 106.89(13) . . ?
O1 C13 C14 108.85(13) . . ?
O2 C13 C12 114.32(13) . . ?
O1 C13 C12 109.99(13) . . ?
C14 C13 C12 111.30(13) . . ?
C13 C14 C15 114.52(13) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C17 C15 C14 110.69(13) . . ?
C17 C15 C16 115.23(12) . . ?
C14 C15 C16 110.23(12) . . ?
C17 C15 H15A 106.7 . . ?
C14 C15 H15A 106.7 . . ?
C16 C15 H15A 106.7 . . ?
O3 C16 O4 111.65(12) . . ?
O3 C16 C15 106.27(12) . . ?
O4 C16 C15 111.99(12) . . ?
O3 C16 C11 111.66(12) . . ?
O4 C16 C11 104.85(12) . . ?
C15 C16 C11 110.53(12) . . ?
C18 C17 C22 118.03(16) . . ?
C18 C17 C15 121.73(15) . . ?
C22 C17 C15 120.22(15) . . ?
C19 C18 C17 120.89(18) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 119.98(18) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.09(19) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.90(18) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 O1 C13 118.91(12) . . ?
C13 O2 H2A 109.5 . . ?
C16 O3 C23 117.40(13) . . ?
C16 O4 C24 118.26(12) . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_1128-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2311553'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-12-01 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2023-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C26 H24 O6'
_chemical_formula_sum            'C26 H24 O6'
_chemical_formula_weight         432.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7261(4)
_cell_length_b                   10.5921(5)
_cell_length_c                   17.2119(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.333(4)
_cell_angle_gamma                90
_cell_volume                     2137.75(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7710
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.6460
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18627
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.238
_diffrn_reflns_theta_min         3.475
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -39.00   1.00    6.90    --  -15.84-178.00 -90.00   49
  2  ω     39.00  89.00   1.00    6.90    --   16.70 178.00-150.00   50
  3  ω     39.00  89.00   1.00    6.90    --   16.70 178.00-180.00   50
  4  ω    -53.00  86.00   1.00    6.90    --   16.70   0.00-120.00  139
  5  ω    -83.00   1.00   1.00    6.90    --  -15.84 -57.00 -90.00   84
  6  ω    -53.00 -18.00   1.00    6.90    --   16.70 -37.00-180.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531204000
_diffrn_orient_matrix_UB_12      0.0158803000
_diffrn_orient_matrix_UB_13      -0.0173311000
_diffrn_orient_matrix_UB_21      -0.0245218000
_diffrn_orient_matrix_UB_22      -0.0555751000
_diffrn_orient_matrix_UB_23      0.0157141000
_diffrn_orient_matrix_UB_31      -0.0152850000
_diffrn_orient_matrix_UB_32      0.0338573000
_diffrn_orient_matrix_UB_33      0.0339270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3932
_reflns_number_total             5124
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²+0.5032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42351(9) 0.35091(10) 0.42909(6) 0.0368(3) Uani 1 1 d . . . . .
O2 O 0.56590(9) 0.21484(11) 0.42182(6) 0.0400(3) Uani 1 1 d . . . . .
O3 O 0.67827(9) 0.07871(12) 0.47964(6) 0.0450(3) Uani 1 1 d . . . . .
O4 O 0.53646(9) 0.00025(10) 0.41197(6) 0.0383(3) Uani 1 1 d . . . . .
O5 O 0.33885(9) 0.12969(11) 0.21606(6) 0.0394(3) Uani 1 1 d . . . . .
O6 O 0.19184(9) 0.27573(11) 0.22329(6) 0.0386(3) Uani 1 1 d . . . . .
C1 C 0.24094(13) 0.56873(17) 0.20835(9) 0.0415(4) Uani 1 1 d . . . . .
H1 H 0.250529 0.500598 0.174943 0.050 Uiso 1 1 calc R . . . .
C2 C 0.18894(16) 0.67584(19) 0.18184(11) 0.0536(5) Uani 1 1 d . . . . .
H2 H 0.164004 0.679714 0.130506 0.064 Uiso 1 1 calc R . . . .
C3 C 0.17257(16) 0.77958(19) 0.23047(13) 0.0578(5) Uani 1 1 d . . . . .
H3 H 0.138779 0.852650 0.211167 0.069 Uiso 1 1 calc R . . . .
C4 C 0.20603(14) 0.77364(16) 0.30591(12) 0.0484(4) Uani 1 1 d . . . . .
H4 H 0.193157 0.842334 0.338345 0.058 Uiso 1 1 calc R . . . .
C5 C 0.26033(12) 0.66446(15) 0.33619(10) 0.0374(3) Uani 1 1 d . . . . .
C6 C 0.28058(12) 0.56003(14) 0.28630(9) 0.0335(3) Uani 1 1 d . . . . .
C7 C 0.33819(12) 0.45095(14) 0.31627(8) 0.0305(3) Uani 1 1 d . . . . .
C8 C 0.36974(12) 0.45151(14) 0.39319(8) 0.0314(3) Uani 1 1 d . . . . .
C9 C 0.34889(13) 0.55392(15) 0.44275(9) 0.0380(3) Uani 1 1 d . . . . .
H9 H 0.371505 0.550301 0.494584 0.046 Uiso 1 1 calc R . . . .
C10 C 0.29573(13) 0.65807(15) 0.41486(10) 0.0409(4) Uani 1 1 d . . . . .
H10 H 0.282337 0.726115 0.447711 0.049 Uiso 1 1 calc R . . . .
C11 C 0.37421(12) 0.34042(14) 0.26681(8) 0.0309(3) Uani 1 1 d . . . . .
H11 H 0.389033 0.371538 0.214206 0.037 Uiso 1 1 calc R . . . .
C12 C 0.48690(12) 0.29198(15) 0.30118(8) 0.0335(3) Uani 1 1 d . . . . .
H12A H 0.516017 0.222378 0.270503 0.040 Uiso 1 1 calc R . . . .
H12B H 0.543479 0.358780 0.302042 0.040 Uiso 1 1 calc R . . . .
C13 C 0.46080(12) 0.24889(14) 0.38247(8) 0.0310(3) Uani 1 1 d . . . . .
C14 C 0.59627(12) 0.09649(15) 0.43967(8) 0.0342(3) Uani 1 1 d . . . . .
C15 C 0.43819(13) 0.02170(15) 0.36245(9) 0.0367(3) Uani 1 1 d . . . . .
H15A H 0.386684 -0.049722 0.365856 0.044 Uiso 1 1 calc R . . . .
H15B H 0.462498 0.029610 0.308894 0.044 Uiso 1 1 calc R . . . .
C16 C 0.37686(12) 0.14068(13) 0.38695(8) 0.0298(3) Uani 1 1 d . . . . .
H16 H 0.355535 0.130599 0.441562 0.036 Uiso 1 1 calc R . . . .
C17 C 0.26522(11) 0.16308(14) 0.33952(8) 0.0292(3) Uani 1 1 d . . . . .
H17 H 0.239283 0.078215 0.325200 0.035 Uiso 1 1 calc R . . . .
C18 C 0.17026(12) 0.21515(15) 0.39130(8) 0.0320(3) Uani 1 1 d . . . . .
C19 C 0.13733(14) 0.13836(18) 0.45291(10) 0.0455(4) Uani 1 1 d . . . . .
H19 H 0.173404 0.061047 0.460265 0.055 Uiso 1 1 calc R . . . .
C20 C 0.05209(16) 0.1747(2) 0.50336(11) 0.0563(5) Uani 1 1 d . . . . .
H20 H 0.031193 0.121761 0.543947 0.068 Uiso 1 1 calc R . . . .
C21 C -0.00177(15) 0.2887(2) 0.49375(11) 0.0532(5) Uani 1 1 d . . . . .
H21 H -0.058064 0.314008 0.528250 0.064 Uiso 1 1 calc R . . . .
C22 C 0.02823(14) 0.36489(17) 0.43277(10) 0.0448(4) Uani 1 1 d . . . . .
H22 H -0.008770 0.441716 0.425630 0.054 Uiso 1 1 calc R . . . .
C23 C 0.11330(13) 0.32858(15) 0.38153(9) 0.0365(3) Uani 1 1 d . . . . .
H23 H 0.132181 0.381044 0.340228 0.044 Uiso 1 1 calc R . . . .
C24 C 0.28943(12) 0.22894(14) 0.26077(8) 0.0307(3) Uani 1 1 d . . . . .
C25 C 0.36753(19) 0.1596(2) 0.13721(10) 0.0613(6) Uani 1 1 d . . . . .
H25A H 0.369725 0.083420 0.107032 0.092 Uiso 1 1 calc GR . . . .
H25B H 0.440907 0.199714 0.135989 0.092 Uiso 1 1 calc GR . . . .
H25C H 0.311137 0.215633 0.115885 0.092 Uiso 1 1 calc GR . . . .
C26 C 0.10529(15) 0.1844(2) 0.20652(11) 0.0542(5) Uani 1 1 d . . . . .
H26A H 0.137473 0.116459 0.176915 0.081 Uiso 1 1 calc GR . . . .
H26B H 0.045098 0.223448 0.177108 0.081 Uiso 1 1 calc GR . . . .
H26C H 0.075216 0.151883 0.254267 0.081 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.3822(17) . ?
O1 C13 1.4166(17) . ?
O2 C13 1.4483(16) . ?
O2 C14 1.3385(19) . ?
O3 C14 1.1941(17) . ?
O4 C14 1.3245(19) . ?
O4 C15 1.4473(17) . ?
O5 C24 1.4277(17) . ?
O5 C25 1.435(2) . ?
O6 C24 1.4009(16) . ?
O6 C26 1.431(2) . ?
C1 C2 1.365(2) . ?
C1 C6 1.420(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.356(3) . ?
C4 C5 1.418(2) . ?
C5 C6 1.421(2) . ?
C5 C10 1.415(2) . ?
C6 C7 1.433(2) . ?
C7 C8 1.373(2) . ?
C7 C11 1.509(2) . ?
C8 C9 1.402(2) . ?
C9 C10 1.354(2) . ?
C11 C12 1.5330(19) . ?
C11 C24 1.547(2) . ?
C12 C13 1.505(2) . ?
C13 C16 1.513(2) . ?
C15 C16 1.512(2) . ?
C16 C17 1.5570(19) . ?
C17 C18 1.5330(19) . ?
C17 C24 1.5521(19) . ?
C18 C19 1.393(2) . ?
C18 C23 1.384(2) . ?
C19 C20 1.383(2) . ?
C20 C21 1.372(3) . ?
C21 C22 1.372(3) . ?
C22 C23 1.390(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
C8 O1 C13 118.45(11) . . ?
C14 O2 C13 124.41(12) . . ?
C14 O4 C15 120.62(12) . . ?
C24 O5 C25 116.43(13) . . ?
C24 O6 C26 115.49(13) . . ?
C2 C1 C6 120.85(17) . . ?
C1 C2 C3 121.11(17) . . ?
C4 C3 C2 119.86(17) . . ?
C3 C4 C5 121.11(18) . . ?
C4 C5 C6 119.27(15) . . ?
C10 C5 C4 121.28(16) . . ?
C10 C5 C6 119.45(14) . . ?
C1 C6 C5 117.73(14) . . ?
C1 C6 C7 122.92(15) . . ?
C5 C6 C7 119.35(13) . . ?
C6 C7 C11 123.73(13) . . ?
C8 C7 C6 117.88(13) . . ?
C8 C7 C11 118.21(13) . . ?
O1 C8 C9 113.90(12) . . ?
C7 C8 O1 123.20(13) . . ?
C7 C8 C9 122.89(14) . . ?
C10 C9 C8 119.75(14) . . ?
C9 C10 C5 120.67(15) . . ?
C7 C11 C12 106.58(12) . . ?
C7 C11 C24 116.63(11) . . ?
C12 C11 C24 108.82(12) . . ?
C13 C12 C11 106.31(11) . . ?
O1 C13 O2 100.93(10) . . ?
O1 C13 C12 111.13(12) . . ?
O1 C13 C16 110.24(11) . . ?
O2 C13 C12 109.46(11) . . ?
O2 C13 C16 109.85(11) . . ?
C12 C13 C16 114.39(12) . . ?
O3 C14 O2 119.49(15) . . ?
O3 C14 O4 120.60(14) . . ?
O4 C14 O2 119.91(12) . . ?
O4 C15 C16 110.18(12) . . ?
C13 C16 C17 113.78(11) . . ?
C15 C16 C13 107.85(12) . . ?
C15 C16 C17 112.37(11) . . ?
C18 C17 C16 111.18(11) . . ?
C18 C17 C24 118.90(12) . . ?
C24 C17 C16 111.64(11) . . ?
C19 C18 C17 115.99(13) . . ?
C23 C18 C17 126.37(13) . . ?
C23 C18 C19 117.62(14) . . ?
C20 C19 C18 121.34(17) . . ?
C21 C20 C19 120.23(17) . . ?
C22 C21 C20 119.35(16) . . ?
C21 C22 C23 120.73(17) . . ?
C18 C23 C22 120.71(15) . . ?
O5 C24 C11 109.61(11) . . ?
O5 C24 C17 102.51(11) . . ?
O6 C24 O5 110.21(11) . . ?
O6 C24 C11 106.50(12) . . ?
O6 C24 C17 114.08(11) . . ?
C11 C24 C17 113.90(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.649
_oxdiff_exptl_absorpt_empirical_full_min 0.463
####################################################################### 
# 
# 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 2253060'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 O4'
_chemical_formula_sum            'C26 H24 O4'
_chemical_formula_weight         400.45

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'

_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                   7.3998(13)
_cell_length_b                   16.299(3)
_cell_length_c                   17.316(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2088.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.3523
_cell_measurement_theta_max      27.1633

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15085
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3696
_reflns_number_gt                3545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0438P)²+0.3259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3696
_refine_ls_number_parameters     275
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3230(3) 0.15664(11) 0.71481(11) 0.0310(4) Uani 1 1 d . . . . .
C2 C 0.1799(3) 0.12684(12) 0.76194(12) 0.0348(5) Uani 1 1 d . . . . .
C3 C 0.0275(3) 0.08615(13) 0.73093(13) 0.0419(5) Uani 1 1 d . . . . .
H3 H 0.016680 0.080020 0.677731 0.050 Uiso 1 1 calc R U . . .
C4 C -0.1038(3) 0.05579(17) 0.77826(16) 0.0570(7) Uani 1 1 d . . . . .
H4 H -0.201885 0.027958 0.757261 0.068 Uiso 1 1 calc R U . . .
C5 C -0.0915(4) 0.0664(2) 0.85842(17) 0.0673(8) Uani 1 1 d . . . . .
H5 H -0.183030 0.046773 0.890287 0.081 Uiso 1 1 calc R U . . .
C6 C 0.0535(4) 0.10511(18) 0.88972(15) 0.0607(7) Uani 1 1 d . . . . .
H6 H 0.059525 0.111727 0.942998 0.073 Uiso 1 1 calc R U . . .
C7 C 0.1956(3) 0.13564(13) 0.84328(12) 0.0423(5) Uani 1 1 d . . . . .
C8 C 0.3531(4) 0.17281(15) 0.87394(13) 0.0485(6) Uani 1 1 d . . . . .
H8 H 0.364508 0.179116 0.927091 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4880(3) 0.19944(13) 0.82661(12) 0.0396(5) Uani 1 1 d . . . . .
H9 H 0.590968 0.222712 0.848258 0.047 Uiso 1 1 calc R U . . .
C10 C 0.4753(3) 0.19258(11) 0.74543(11) 0.0314(4) Uani 1 1 d . . . . .
C11 C 0.6289(3) 0.21503(12) 0.69244(11) 0.0294(4) Uani 1 1 d . . . . .
H11 H 0.742324 0.207580 0.720786 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6213(3) 0.30481(11) 0.66333(10) 0.0284(4) Uani 1 1 d . . . . .
C13 C 0.4520(3) 0.31858(12) 0.61230(11) 0.0296(4) Uani 1 1 d . . . . .
H13 H 0.346092 0.319588 0.646291 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4244(3) 0.24904(12) 0.55304(11) 0.0318(4) Uani 1 1 d . . . . .
H14A H 0.303943 0.253999 0.531441 0.038 Uiso 1 1 calc R U . . .
H14B H 0.509887 0.256668 0.511182 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4468(3) 0.16293(12) 0.58457(10) 0.0311(4) Uani 1 1 d . . . . .
C16 C 0.6266(3) 0.15437(12) 0.62528(11) 0.0319(4) Uani 1 1 d . . . . .
H16A H 0.724626 0.166251 0.589825 0.038 Uiso 1 1 calc R U . . .
H16B H 0.641461 0.098803 0.644321 0.038 Uiso 1 1 calc R U . . .
C17 C 0.4531(3) 0.39532(12) 0.56758(12) 0.0354(5) Uani 1 1 d . . . . .
C18 C 0.4510(3) 0.45098(13) 0.52261(12) 0.0396(5) Uani 1 1 d . . . . .
C19 C 0.4436(4) 0.51860(12) 0.46924(12) 0.0426(5) Uani 1 1 d . . . . .
C20 C 0.6010(5) 0.55398(15) 0.44142(16) 0.0618(7) Uani 1 1 d . . . . .
H20 H 0.713038 0.534130 0.456957 0.074 Uiso 1 1 calc R U . . .
C21 C 0.5899(6) 0.61941(19) 0.39008(19) 0.0822(9) Uani 1 1 d . U . . .
H21 H 0.694833 0.644009 0.371689 0.099 Uiso 1 1 calc R U . . .
C22 C 0.4230(7) 0.64785(19) 0.36642(19) 0.0927(11) Uani 1 1 d . U . . .
H22 H 0.416572 0.691931 0.332435 0.111 Uiso 1 1 calc R U . . .
C23 C 0.2675(6) 0.6122(2) 0.39217(18) 0.0822(10) Uani 1 1 d . U . . .
H23 H 0.156036 0.631529 0.375215 0.099 Uiso 1 1 calc R U . . .
C24 C 0.2758(4) 0.54720(15) 0.44368(14) 0.0562(7) Uani 1 1 d . . . . .
H24 H 0.170053 0.522648 0.461189 0.067 Uiso 1 1 calc R U . . .
C25 C 0.6177(4) 0.43983(13) 0.72295(15) 0.0528(6) Uani 1 1 d . . . . .
H25A H 0.705739 0.456256 0.685274 0.079 Uiso 1 1 calc R U . . .
H25B H 0.645817 0.464718 0.771742 0.079 Uiso 1 1 calc R U . . .
H25C H 0.499817 0.457156 0.706529 0.079 Uiso 1 1 calc R U . . .
C26 C 0.9464(3) 0.31805(17) 0.65099(14) 0.0483(6) Uani 1 1 d . . . . .
H26A H 1.032245 0.349549 0.621854 0.073 Uiso 1 1 calc R U . . .
H26B H 0.983932 0.261684 0.652356 0.073 Uiso 1 1 calc R U . . .
H26C H 0.939735 0.339067 0.702698 0.073 Uiso 1 1 calc R U . . .
O1 O 0.29783(19) 0.14597(9) 0.63687(7) 0.0377(4) Uani 1 1 d . . . . .
O2 O 0.4344(2) 0.10422(9) 0.52618(8) 0.0413(4) Uani 1 1 d . . . . .
H2 H 0.349144 0.115348 0.497798 0.062 Uiso 1 1 calc R U . . .
O3 O 0.6203(2) 0.35244(8) 0.73086(7) 0.0359(3) Uani 1 1 d . . . . .
O4 O 0.77127(17) 0.32382(9) 0.61505(8) 0.0336(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.374(2) . ?
C1 C10 1.376(3) . ?
C1 C2 1.423(3) . ?
C2 C3 1.414(3) . ?
C2 C7 1.421(3) . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.414(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.416(4) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.413(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.506(3) . ?
C11 C16 1.526(3) . ?
C11 C12 1.549(3) . ?
C11 H11 0.9800 . ?
C12 O3 1.404(2) . ?
C12 O4 1.423(2) . ?
C12 C13 1.550(3) . ?
C13 C17 1.471(3) . ?
C13 C14 1.542(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O2 1.395(2) . ?
C15 O1 1.453(2) . ?
C15 C16 1.512(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.196(3) . ?
C18 C19 1.439(3) . ?
C19 C20 1.386(4) . ?
C19 C24 1.398(4) . ?
C20 C21 1.391(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 O3 1.431(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O4 1.441(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O2 H2 0.8200 . ?

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
O1 C1 C10 122.94(17) . . ?
O1 C1 C2 114.79(17) . . ?
C10 C1 C2 122.28(18) . . ?
C3 C2 C7 119.30(19) . . ?
C3 C2 C1 122.42(19) . . ?
C7 C2 C1 118.2(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 123.3(2) . . ?
C6 C7 C2 117.8(2) . . ?
C8 C7 C2 118.8(2) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.12(19) . . ?
C1 C10 C11 119.11(17) . . ?
C9 C10 C11 122.47(19) . . ?
C10 C11 C16 107.37(16) . . ?
C10 C11 C12 113.62(16) . . ?
C16 C11 C12 111.33(15) . . ?
C10 C11 H11 108.1 . . ?
C16 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
O3 C12 O4 111.90(15) . . ?
O3 C12 C11 104.57(14) . . ?
O4 C12 C11 111.62(15) . . ?
O3 C12 C13 113.00(16) . . ?
O4 C12 C13 105.31(14) . . ?
C11 C12 C13 110.58(15) . . ?
C17 C13 C14 105.98(15) . . ?
C17 C13 C12 114.75(16) . . ?
C14 C13 C12 112.33(15) . . ?
C17 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C12 C13 H13 107.8 . . ?
C15 C14 C13 115.24(15) . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O2 C15 O1 105.74(15) . . ?
O2 C15 C16 109.42(16) . . ?
O1 C15 C16 111.06(14) . . ?
O2 C15 C14 111.53(15) . . ?
O1 C15 C14 108.53(16) . . ?
C16 C15 C14 110.47(16) . . ?
C15 C16 C11 107.77(15) . . ?
C15 C16 H16A 110.2 . . ?
C11 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C11 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C18 C17 C13 171.1(2) . . ?
C17 C18 C19 178.4(2) . . ?
C20 C19 C24 119.8(2) . . ?
C20 C19 C18 120.7(2) . . ?
C24 C19 C18 119.5(2) . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 119.9(3) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 O1 C15 119.03(14) . . ?
C15 O2 H2 109.5 . . ?
C12 O3 C25 118.08(16) . . ?
C12 O4 C26 115.69(15) . . ?

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 C2 C3 2.7(3) . . . . ?
C10 C1 C2 C3 -176.70(19) . . . . ?
O1 C1 C2 C7 -179.94(17) . . . . ?
C10 C1 C2 C7 0.6(3) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 177.6(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C4 C5 C6 -1.7(5) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 -176.8(3) . . . . ?
C5 C6 C7 C2 1.9(4) . . . . ?
C3 C2 C7 C6 -1.9(3) . . . . ?
C1 C2 C7 C6 -179.4(2) . . . . ?
C3 C2 C7 C8 176.8(2) . . . . ?
C1 C2 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 178.4(2) . . . . ?
C2 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 1.2(4) . . . . ?
O1 C1 C10 C9 -179.19(18) . . . . ?
C2 C1 C10 C9 0.2(3) . . . . ?
O1 C1 C10 C11 -5.3(3) . . . . ?
C2 C1 C10 C11 174.03(17) . . . . ?
C8 C9 C10 C1 -1.1(3) . . . . ?
C8 C9 C10 C11 -174.7(2) . . . . ?
C1 C10 C11 C16 -29.8(2) . . . . ?
C9 C10 C11 C16 143.77(19) . . . . ?
C1 C10 C11 C12 93.7(2) . . . . ?
C9 C10 C11 C12 -92.7(2) . . . . ?
C10 C11 C12 O3 57.4(2) . . . . ?
C16 C11 C12 O3 178.73(15) . . . . ?
C10 C11 C12 O4 178.54(15) . . . . ?
C16 C11 C12 O4 -60.1(2) . . . . ?
C10 C11 C12 C13 -64.6(2) . . . . ?
C16 C11 C12 C13 56.8(2) . . . . ?
O3 C12 C13 C17 76.5(2) . . . . ?
O4 C12 C13 C17 -45.9(2) . . . . ?
C11 C12 C13 C17 -166.67(16) . . . . ?
O3 C12 C13 C14 -162.37(15) . . . . ?
O4 C12 C13 C14 75.19(18) . . . . ?
C11 C12 C13 C14 -45.5(2) . . . . ?
C17 C13 C14 C15 171.20(16) . . . . ?
C12 C13 C14 C15 45.2(2) . . . . ?
C13 C14 C15 O2 -175.11(17) . . . . ?
C13 C14 C15 O1 68.8(2) . . . . ?
C13 C14 C15 C16 -53.2(2) . . . . ?
O2 C15 C16 C11 -175.73(15) . . . . ?
O1 C15 C16 C11 -59.37(19) . . . . ?
C14 C15 C16 C11 61.11(19) . . . . ?
C10 C11 C16 C15 60.43(19) . . . . ?
C12 C11 C16 C15 -64.5(2) . . . . ?
C24 C19 C20 C21 2.0(4) . . . . ?
C18 C19 C20 C21 -179.8(2) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C21 C22 C23 C24 0.9(5) . . . . ?
C22 C23 C24 C19 0.2(5) . . . . ?
C20 C19 C24 C23 -1.7(4) . . . . ?
C18 C19 C24 C23 -179.9(2) . . . . ?
C10 C1 O1 C15 8.5(3) . . . . ?
C2 C1 O1 C15 -170.89(16) . . . . ?
O2 C15 O1 C1 143.46(16) . . . . ?
C16 C15 O1 C1 24.9(2) . . . . ?
C14 C15 O1 C1 -96.76(19) . . . . ?
O4 C12 O3 C25 57.7(2) . . . . ?
C11 C12 O3 C25 178.65(19) . . . . ?
C13 C12 O3 C25 -61.0(2) . . . . ?
O3 C12 O4 C26 54.9(2) . . . . ?
C11 C12 O4 C26 -61.9(2) . . . . ?
C13 C12 O4 C26 178.05(18) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_0123-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2327657'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2024-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         '0.44(C24 H23 I O4)'
_chemical_formula_sum            'C10.67 H10.22 I0.44 O1.78'
_chemical_formula_weight         223.25
_chemical_absolute_configuration ab
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.7566(3)
_cell_length_b                   15.3110(4)
_cell_length_c                   20.2975(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2099.78(12)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.3180
_cell_measurement_theta_min      4.0060
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    1.553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13930
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.196
_diffrn_reflns_theta_min         3.296
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  51.00   1.00    5.27    --  -15.92  57.00   0.00   84
  2  ω    -88.00 -39.00   1.00    5.27    --  -15.92-178.00  60.00   49
  3  ω     39.00  89.00   1.00    5.27    --   16.85 178.00-150.00   50
  4  ω    -85.00 -29.00   1.00    5.27    --  -15.92 -37.00  30.00   56
  5  ω    -42.00  11.00   1.00    5.27    --  -15.92 -77.00 -60.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0511738000
_diffrn_orient_matrix_UB_12      0.0362539000
_diffrn_orient_matrix_UB_13      0.0135591000
_diffrn_orient_matrix_UB_21      -0.0642189000
_diffrn_orient_matrix_UB_22      -0.0005096000
_diffrn_orient_matrix_UB_23      0.0276339000
_diffrn_orient_matrix_UB_31      0.0653541000
_diffrn_orient_matrix_UB_32      -0.0288439000
_diffrn_orient_matrix_UB_33      0.0165575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.607
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                4020
_reflns_number_total             4790
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1290 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+0.7456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0665
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006), C008(H008), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00F(H00C,H00D,H00E), C00M(H00F,H00K,H00M)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.15594(6) 0.04473(2) 0.79455(2) 0.05412(12) Uani 1 1 d . . . . .
O002 O 0.1674(5) 0.17147(18) 0.66533(13) 0.0356(7) Uani 1 1 d . . . . .
O003 O -0.1257(5) 0.1818(2) 0.71778(15) 0.0433(8) Uani 1 1 d . . . . .
H003 H -0.188516 0.208031 0.689425 0.065 Uiso 1 1 calc GR . . . .
O004 O 0.5786(4) 0.34984(19) 0.78220(13) 0.0351(7) Uani 1 1 d . . . . .
O005 O 0.2687(5) 0.36102(19) 0.83393(14) 0.0373(8) Uani 1 1 d . . . . .
C006 C 0.1572(7) 0.1858(2) 0.78543(19) 0.0298(9) Uani 1 1 d . . . . .
H006 H 0.072649 0.209279 0.820424 0.036 Uiso 1 1 calc R . . . .
C007 C 0.3340(8) 0.2106(3) 0.63915(18) 0.0301(9) Uani 1 1 d . . . . .
C008 C 0.3684(7) 0.2192(2) 0.79772(19) 0.0278(9) Uani 1 1 d . . . . .
H008 H 0.452837 0.191160 0.764671 0.033 Uiso 1 1 calc R . . . .
C009 C 0.2978(6) 0.3381(3) 0.7146(2) 0.0298(10) Uani 1 1 d . . . . .
H009 H 0.308216 0.400835 0.705741 0.036 Uiso 1 1 calc R . . . .
C00A C 0.0677(6) 0.2135(3) 0.7196(2) 0.0314(10) Uani 1 1 d . . . . .
C00B C 0.0809(6) 0.3118(3) 0.7122(2) 0.0334(10) Uani 1 1 d . . . . .
H00A H 0.008865 0.340213 0.747599 0.040 Uiso 1 1 calc R . . . .
H00B H 0.022947 0.329710 0.670641 0.040 Uiso 1 1 calc R . . . .
C00C C 0.4063(7) 0.2888(3) 0.66110(19) 0.0297(10) Uani 1 1 d . . . . .
C00D C 0.4228(7) 0.1633(3) 0.5867(2) 0.0337(11) Uani 1 1 d . . . . .
C00E C 0.3800(6) 0.3194(3) 0.78441(19) 0.0298(9) Uani 1 1 d . . . . .
C00F C 0.2612(8) 0.4551(3) 0.8312(2) 0.0516(13) Uani 1 1 d . . . . .
H00C H 0.149896 0.472957 0.805023 0.077 Uiso 1 1 calc GR . . . .
H00D H 0.380887 0.476883 0.811662 0.077 Uiso 1 1 calc GR . . . .
H00E H 0.247841 0.478099 0.874931 0.077 Uiso 1 1 calc GR . . . .
C00G C 0.5782(7) 0.3221(3) 0.6307(2) 0.0371(11) Uani 1 1 d . . . . .
H00G H 0.628941 0.375431 0.644705 0.045 Uiso 1 1 calc R . . . .
C00H C 0.6311(8) 0.1511(3) 0.8678(2) 0.0467(13) Uani 1 1 d . . . . .
H00H H 0.703713 0.142460 0.829420 0.056 Uiso 1 1 calc R . . . .
C00I C 0.6714(8) 0.2782(3) 0.5815(2) 0.0433(12) Uani 1 1 d . . . . .
H00I H 0.786140 0.301272 0.563131 0.052 Uiso 1 1 calc R . . . .
C00J C 0.3409(10) 0.0857(3) 0.5610(2) 0.0467(12) Uani 1 1 d . . . . .
H00J H 0.225864 0.062761 0.579262 0.056 Uiso 1 1 calc R . . . .
C00K C 0.5971(8) 0.1985(3) 0.5580(2) 0.0394(12) Uani 1 1 d . . . . .
C00L C 0.6030(11) 0.0783(4) 0.4812(3) 0.069(2) Uani 1 1 d . . . . .
H00L H 0.661385 0.049954 0.445619 0.082 Uiso 1 1 calc R . . . .
C00M C 0.6812(8) 0.3636(3) 0.8428(2) 0.0460(12) Uani 1 1 d . . . . .
H00F H 0.751178 0.418074 0.840938 0.069 Uiso 1 1 calc GR . . . .
H00K H 0.773630 0.316839 0.849762 0.069 Uiso 1 1 calc GR . . . .
H00M H 0.587850 0.364984 0.878429 0.069 Uiso 1 1 calc GR . . . .
C00N C 0.4472(8) 0.1910(3) 0.8647(2) 0.0347(11) Uani 1 1 d . . . . .
C00O C 0.4299(10) 0.0440(4) 0.5092(2) 0.0648(17) Uani 1 1 d . . . . .
H00O H 0.375468 -0.007241 0.492527 0.078 Uiso 1 1 calc R . . . .
C00P C 0.6861(10) 0.1522(4) 0.5051(2) 0.0568(15) Uani 1 1 d . . . . .
H00P H 0.803121 0.172931 0.486762 0.068 Uiso 1 1 calc R . . . .
C00Q C 0.3410(11) 0.2035(3) 0.9221(2) 0.0498(13) Uani 1 1 d . . . . .
H00Q H 0.218614 0.231273 0.920660 0.060 Uiso 1 1 calc R . . . .
C00R C 0.7068(11) 0.1241(4) 0.9276(3) 0.071(2) Uani 1 1 d . . . . .
H00R H 0.830698 0.097671 0.929260 0.085 Uiso 1 1 calc R . . . .
C00S C 0.4171(12) 0.1746(4) 0.9820(3) 0.073(2) Uani 1 1 d . . . . .
H00S H 0.343811 0.181493 1.020397 0.088 Uiso 1 1 calc R . . . .
C00T C 0.6018(14) 0.1358(4) 0.9843(3) 0.085(3) Uani 1 1 d . . . . .
H00T H 0.654132 0.117631 1.024421 0.102 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I001 C006 2.168(4) . ?
O002 C007 1.381(6) . ?
O002 C00A 1.443(5) . ?
O003 C00A 1.394(5) . ?
O004 C00E 1.421(5) . ?
O004 C00M 1.427(5) . ?
O005 C00E 1.407(5) . ?
O005 C00F 1.443(6) . ?
C006 C008 1.536(6) . ?
C006 C00A 1.527(6) . ?
C007 C00C 1.368(6) . ?
C007 C00D 1.421(6) . ?
C008 C00E 1.560(5) . ?
C008 C00N 1.523(5) . ?
C009 C00B 1.520(6) . ?
C009 C00C 1.512(6) . ?
C009 C00E 1.549(5) . ?
C00A C00B 1.516(6) . ?
C00C C00G 1.410(6) . ?
C00D C00J 1.411(6) . ?
C00D C00K 1.420(7) . ?
C00G C00I 1.359(6) . ?
C00H C00N 1.386(7) . ?
C00H C00R 1.381(7) . ?
C00I C00K 1.403(7) . ?
C00J C00O 1.369(7) . ?
C00K C00P 1.419(7) . ?
C00L C00O 1.403(8) . ?
C00L C00P 1.354(8) . ?
C00N C00Q 1.380(7) . ?
C00Q C00S 1.392(7) . ?
C00R C00T 1.364(9) . ?
C00S C00T 1.383(10) . ?

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
C007 O002 C00A 118.8(3) . . ?
C00E O004 C00M 118.7(3) . . ?
C00E O005 C00F 116.3(3) . . ?
C008 C006 I001 108.8(3) . . ?
C00A C006 I001 110.5(3) . . ?
C00A C006 C008 114.7(3) . . ?
O002 C007 C00D 114.3(4) . . ?
C00C C007 O002 123.0(4) . . ?
C00C C007 C00D 122.7(5) . . ?
C006 C008 C00E 110.3(3) . . ?
C00N C008 C006 112.0(4) . . ?
C00N C008 C00E 114.6(3) . . ?
C00B C009 C00E 109.0(4) . . ?
C00C C009 C00B 108.2(3) . . ?
C00C C009 C00E 113.0(3) . . ?
O002 C00A C006 111.1(3) . . ?
O002 C00A C00B 109.9(3) . . ?
O003 C00A O002 105.2(3) . . ?
O003 C00A C006 107.3(4) . . ?
O003 C00A C00B 113.5(4) . . ?
C00B C00A C006 109.8(3) . . ?
C00A C00B C009 108.4(3) . . ?
C007 C00C C009 119.8(4) . . ?
C007 C00C C00G 117.9(4) . . ?
C00G C00C C009 122.2(4) . . ?
C00J C00D C007 122.7(5) . . ?
C00J C00D C00K 119.6(4) . . ?
C00K C00D C007 117.7(4) . . ?
O004 C00E C008 112.0(3) . . ?
O004 C00E C009 104.4(3) . . ?
O005 C00E O004 112.3(3) . . ?
O005 C00E C008 107.1(3) . . ?
O005 C00E C009 112.2(3) . . ?
C009 C00E C008 108.8(3) . . ?
C00I C00G C00C 121.6(5) . . ?
C00R C00H C00N 120.2(6) . . ?
C00G C00I C00K 121.0(5) . . ?
C00O C00J C00D 120.3(6) . . ?
C00I C00K C00D 119.2(4) . . ?
C00I C00K C00P 122.7(5) . . ?
C00P C00K C00D 118.2(5) . . ?
C00P C00L C00O 120.9(5) . . ?
C00H C00N C008 118.6(4) . . ?
C00Q C00N C008 122.1(5) . . ?
C00Q C00N C00H 119.3(5) . . ?
C00J C00O C00L 120.2(6) . . ?
C00L C00P C00K 120.9(6) . . ?
C00N C00Q C00S 120.0(6) . . ?
C00T C00R C00H 120.6(6) . . ?
C00T C00S C00Q 120.0(6) . . ?
C00R C00T C00S 119.8(6) . . ?

_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 1.312
_oxdiff_exptl_absorpt_empirical_full_min 0.760
