# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_222
_database_code_depnum_ccdc_archive 'CCDC 2419631'
loop_
_audit_author_name
_audit_author_address
b
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2019-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 O'
_chemical_formula_sum            'C28 H24 O'
_chemical_formula_weight         376.47
_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                   12.5483(6)
_cell_length_b                   13.9712(7)
_cell_length_c                   12.1835(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.770(2)
_cell_angle_gamma                90
_cell_volume                     2125.13(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.698
_cell_measurement_theta_min      3.264
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0771 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8670.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28237
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_min         3.263
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3170
_reflns_number_total             4885
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0736
_refine_ls_restrained_S_all      1.014
_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)+(0.0920P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1834
_refine_ls_wR_factor_ref         0.2100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C18(H18A,H18B), C20(H20A,H20B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C5(H5), C1(H1), C26(H26), C23(H23), C10(H10), C25(H25),
 C24(H24), C11(H11), C2(H2), C12(H12), C3(H3), C4(H4), C17(H17)
;
_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 0.43132(17) 0.02229(16) 0.31124(19) 0.0805(7) Uani 1 1 d . . . . .
C14 C 0.34661(16) 0.07582(15) 0.47222(18) 0.0385(5) Uani 1 1 d . . . . .
C7 C 0.28939(16) -0.00156(14) 0.49738(18) 0.0368(5) Uani 1 1 d . . . . .
C15 C 0.35163(17) 0.17150(15) 0.53421(17) 0.0367(5) Uani 1 1 d . . . . .
H15 H 0.389286 0.162799 0.607976 0.044 Uiso 1 1 calc R . . . .
C8 C 0.23734(17) -0.00549(14) 0.60129(19) 0.0393(5) Uani 1 1 d . . . . .
C6 C 0.26499(16) -0.08348(15) 0.4206(2) 0.0409(5) Uani 1 1 d . . . . .
C22 C 0.41892(17) 0.23257(16) 0.46507(19) 0.0414(5) Uani 1 1 d . . . . .
C16 C 0.24226(18) 0.21598(16) 0.54379(18) 0.0410(5) Uani 1 1 d . . . . .
C27 C 0.45164(17) 0.18311(18) 0.37668(19) 0.0435(5) Uani 1 1 d . . . . .
C28 C 0.41141(18) 0.08423(18) 0.3762(2) 0.0480(6) Uani 1 1 d . . . . .
C9 C 0.2944(2) 0.00916(17) 0.7034(2) 0.0507(6) Uani 1 1 d . . . . .
H9 H 0.368115 0.018611 0.708373 0.061 Uiso 1 1 calc R . . . .
C13 C 0.12842(19) -0.02368(19) 0.5969(2) 0.0535(6) Uani 1 1 d . . . . .
H13 H 0.089840 -0.037137 0.529428 0.064 Uiso 1 1 calc R . . . .
C5 C 0.2808(2) -0.17706(18) 0.4570(2) 0.0566(7) Uani 1 1 d . . . . .
H5 H 0.310584 -0.188821 0.528694 0.068 Uiso 1 1 calc R . . . .
C1 C 0.21812(19) -0.06887(19) 0.3151(2) 0.0518(6) Uani 1 1 d . . . . .
H1 H 0.206634 -0.006744 0.289209 0.062 Uiso 1 1 calc R . . . .
C26 C 0.51296(19) 0.2262(2) 0.3008(2) 0.0557(7) Uani 1 1 d . . . . .
H26 H 0.534766 0.191956 0.241545 0.067 Uiso 1 1 calc R . . . .
C23 C 0.4478(2) 0.32786(18) 0.4809(2) 0.0560(7) Uani 1 1 d . . . . .
H23 H 0.427237 0.362112 0.540739 0.067 Uiso 1 1 calc R . . . .
C21 C 0.1688(2) 0.2235(2) 0.4416(2) 0.0658(8) Uani 1 1 d . . . . .
H21A H 0.161444 0.160601 0.407898 0.079 Uiso 1 1 calc R . . . .
H21B H 0.201175 0.265148 0.390532 0.079 Uiso 1 1 calc R . . . .
C10 C 0.2418(3) 0.0097(2) 0.7978(2) 0.0679(8) Uani 1 1 d . . . . .
H10 H 0.280223 0.019874 0.866133 0.082 Uiso 1 1 calc R . . . .
C25 C 0.5399(2) 0.3204(2) 0.3164(3) 0.0662(8) Uani 1 1 d . . . . .
H25 H 0.580147 0.351033 0.266773 0.079 Uiso 1 1 calc R . . . .
C24 C 0.5079(2) 0.3706(2) 0.4051(3) 0.0681(8) Uani 1 1 d . . . . .
H24 H 0.527238 0.434566 0.414136 0.082 Uiso 1 1 calc R . . . .
C11 C 0.1335(3) -0.0046(2) 0.7912(3) 0.0755(10) Uani 1 1 d . . . . .
H11 H 0.098362 -0.002535 0.854795 0.091 Uiso 1 1 calc R . . . .
C2 C 0.1877(2) -0.1455(2) 0.2469(3) 0.0689(8) Uani 1 1 d . . . . .
H2 H 0.155164 -0.134560 0.176042 0.083 Uiso 1 1 calc R . . . .
C18 C 0.1116(3) 0.3000(3) 0.6481(3) 0.1037(14) Uani 1 1 d . . . . .
H18A H 0.069208 0.256999 0.688658 0.124 Uiso 1 1 calc R . . . .
H18B H 0.123531 0.358021 0.691284 0.124 Uiso 1 1 calc R . . . .
C12 C 0.0768(2) -0.0220(2) 0.6913(3) 0.0727(9) Uani 1 1 d . . . . .
H12 H 0.003354 -0.032704 0.687226 0.087 Uiso 1 1 calc R . . . .
C3 C 0.2057(3) -0.2374(2) 0.2838(3) 0.0731(9) Uani 1 1 d . . . . .
H3 H 0.185753 -0.288930 0.237853 0.088 Uiso 1 1 calc R . . . .
C4 C 0.2525(3) -0.25285(19) 0.3872(3) 0.0725(9) Uani 1 1 d . . . . .
H4 H 0.265741 -0.315194 0.411572 0.087 Uiso 1 1 calc R . . . .
C17 C 0.2175(3) 0.2540(3) 0.6361(2) 0.0782(10) Uani 1 1 d . . . . .
H17 H 0.268211 0.252348 0.697234 0.094 Uiso 1 1 calc R . . . .
C20 C 0.0605(3) 0.2604(3) 0.4564(3) 0.1020(14) Uani 1 1 d . . . . .
H20A H 0.032821 0.291748 0.388393 0.122 Uiso 1 1 calc R . . . .
H20B H 0.014507 0.205969 0.466441 0.122 Uiso 1 1 calc R . . . .
C19 C 0.0506(4) 0.3239(5) 0.5426(3) 0.137(2) Uani 1 1 d . . . . .
H19A H -0.024512 0.328283 0.554437 0.165 Uiso 1 1 calc R . . . .
H19B H 0.073043 0.386779 0.520102 0.165 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
O1 C28 1.215(3) . ?
C14 C7 1.350(3) . ?
C14 C15 1.534(3) . ?
C14 C28 1.495(3) . ?
C7 C8 1.483(3) . ?
C7 C6 1.490(3) . ?
C15 H15 0.9800 . ?
C15 C22 1.514(3) . ?
C15 C16 1.522(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.386(3) . ?
C6 C5 1.388(3) . ?
C6 C1 1.374(3) . ?
C22 C27 1.377(3) . ?
C22 C23 1.388(3) . ?
C16 C21 1.477(3) . ?
C16 C17 1.309(3) . ?
C27 C28 1.471(3) . ?
C27 C26 1.398(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.376(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.367(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.482(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(5) . ?
C25 H25 0.9300 . ?
C25 C24 1.381(4) . ?
C24 H24 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.369(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.496(5) . ?
C18 C19 1.467(5) . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.352(5) . ?
C4 H4 0.9300 . ?
C17 H17 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.390(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C7 C14 C15 125.64(19) . . ?
C7 C14 C28 125.7(2) . . ?
C28 C14 C15 108.56(18) . . ?
C14 C7 C8 120.91(19) . . ?
C14 C7 C6 123.6(2) . . ?
C8 C7 C6 115.27(18) . . ?
C14 C15 H15 109.6 . . ?
C22 C15 C14 102.40(17) . . ?
C22 C15 H15 109.6 . . ?
C22 C15 C16 111.73(18) . . ?
C16 C15 C14 113.65(17) . . ?
C16 C15 H15 109.6 . . ?
C9 C8 C7 121.9(2) . . ?
C13 C8 C7 119.4(2) . . ?
C13 C8 C9 118.7(2) . . ?
C5 C6 C7 120.6(2) . . ?
C1 C6 C7 121.0(2) . . ?
C1 C6 C5 118.2(2) . . ?
C27 C22 C15 112.3(2) . . ?
C27 C22 C23 119.7(2) . . ?
C23 C22 C15 128.0(2) . . ?
C21 C16 C15 117.09(19) . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 C21 120.9(2) . . ?
C22 C27 C28 110.2(2) . . ?
C22 C27 C26 121.9(2) . . ?
C26 C27 C28 127.9(2) . . ?
O1 C28 C14 128.1(2) . . ?
O1 C28 C27 125.4(2) . . ?
C27 C28 C14 106.50(19) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C1 H1 119.6 . . ?
C6 C1 C2 120.9(3) . . ?
C2 C1 H1 119.6 . . ?
C27 C26 H26 121.1 . . ?
C25 C26 C27 117.9(3) . . ?
C25 C26 H26 121.1 . . ?
C22 C23 H23 120.9 . . ?
C24 C23 C22 118.2(3) . . ?
C24 C23 H23 120.9 . . ?
C16 C21 H21A 108.5 . . ?
C16 C21 H21B 108.5 . . ?
C16 C21 C20 115.1(2) . . ?
H21A C21 H21B 107.5 . . ?
C20 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C26 C25 H25 119.7 . . ?
C26 C25 C24 120.7(3) . . ?
C24 C25 H25 119.7 . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.6(3) . . ?
C25 C24 H24 119.2 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
H18A C18 H18B 107.7 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C19 C18 C17 113.7(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C16 C17 C18 123.2(3) . . ?
C16 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C21 C20 H20A 107.8 . . ?
C21 C20 H20B 107.8 . . ?
H20A C20 H20B 107.2 . . ?
C19 C20 C21 117.8(3) . . ?
C19 C20 H20A 107.8 . . ?
C19 C20 H20B 107.8 . . ?
C18 C19 H19A 108.3 . . ?
C18 C19 H19B 108.3 . . ?
C20 C19 C18 116.0(4) . . ?
C20 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?

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
C14 C7 C8 C9 -54.4(3) . . . . ?
C14 C7 C8 C13 125.2(2) . . . . ?
C14 C7 C6 C5 132.3(2) . . . . ?
C14 C7 C6 C1 -53.1(3) . . . . ?
C14 C15 C22 C27 -0.9(2) . . . . ?
C14 C15 C22 C23 178.3(2) . . . . ?
C14 C15 C16 C21 -49.7(3) . . . . ?
C14 C15 C16 C17 136.4(3) . . . . ?
C7 C14 C15 C22 -175.5(2) . . . . ?
C7 C14 C15 C16 -54.9(3) . . . . ?
C7 C14 C28 O1 -6.9(4) . . . . ?
C7 C14 C28 C27 175.3(2) . . . . ?
C7 C8 C9 C10 176.7(2) . . . . ?
C7 C8 C13 C12 -176.0(2) . . . . ?
C7 C6 C5 C4 176.4(2) . . . . ?
C7 C6 C1 C2 -174.8(2) . . . . ?
C15 C14 C7 C8 -9.6(3) . . . . ?
C15 C14 C7 C6 164.3(2) . . . . ?
C15 C14 C28 O1 175.8(3) . . . . ?
C15 C14 C28 C27 -2.0(2) . . . . ?
C15 C22 C27 C28 -0.3(3) . . . . ?
C15 C22 C27 C26 178.8(2) . . . . ?
C15 C22 C23 C24 -178.3(2) . . . . ?
C15 C16 C21 C20 175.6(3) . . . . ?
C15 C16 C17 C18 178.8(3) . . . . ?
C8 C7 C6 C5 -53.4(3) . . . . ?
C8 C7 C6 C1 121.1(2) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C8 C13 C12 C11 -1.6(4) . . . . ?
C6 C7 C8 C9 131.2(2) . . . . ?
C6 C7 C8 C13 -49.2(3) . . . . ?
C6 C5 C4 C3 -2.3(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C22 C15 C16 C21 65.6(3) . . . . ?
C22 C15 C16 C17 -108.3(3) . . . . ?
C22 C27 C28 O1 -176.4(3) . . . . ?
C22 C27 C28 C14 1.5(3) . . . . ?
C22 C27 C26 C25 -0.2(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C16 C15 C22 C27 -122.9(2) . . . . ?
C16 C15 C22 C23 56.4(3) . . . . ?
C16 C21 C20 C19 29.8(6) . . . . ?
C27 C22 C23 C24 0.9(4) . . . . ?
C27 C26 C25 C24 0.5(4) . . . . ?
C28 C14 C7 C8 173.5(2) . . . . ?
C28 C14 C7 C6 -12.5(3) . . . . ?
C28 C14 C15 C22 1.8(2) . . . . ?
C28 C14 C15 C16 122.4(2) . . . . ?
C28 C27 C26 C25 178.7(2) . . . . ?
C9 C8 C13 C12 3.5(4) . . . . ?
C9 C10 C11 C12 1.6(5) . . . . ?
C13 C8 C9 C10 -2.9(3) . . . . ?
C5 C6 C1 C2 -0.2(4) . . . . ?
C1 C6 C5 C4 1.7(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C26 C27 C28 O1 4.5(4) . . . . ?
C26 C27 C28 C14 -177.6(2) . . . . ?
C26 C25 C24 C23 -0.1(4) . . . . ?
C23 C22 C27 C28 -179.6(2) . . . . ?
C23 C22 C27 C26 -0.5(3) . . . . ?
C21 C16 C17 C18 5.2(5) . . . . ?
C21 C20 C19 C18 -43.0(7) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C17 C16 C21 C20 -10.5(5) . . . . ?
C17 C18 C19 C20 35.3(7) . . . . ?
C19 C18 C17 C16 -16.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_zhuhait_1122_auto
_database_code_depnum_ccdc_archive 'CCDC 2419635'
loop_
_audit_author_name
_audit_author_address
a
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-11-22
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H23 Cl O'
_chemical_formula_sum            'C31 H23 Cl O'
_chemical_formula_weight         446.94
_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'
Cl Cl 0.1484 0.1585 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   14.6422(8)
_cell_length_b                   12.5662(6)
_cell_length_c                   26.0642(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4795.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6146
_cell_measurement_temperature    292(4)
_cell_measurement_theta_max      30.1880
_cell_measurement_theta_min      2.0920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26303
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.045
_diffrn_reflns_theta_min         2.092
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  -9.00   1.00    3.00    --    3.89 -40.00 -35.00   60
  2  ω    -62.00 -32.00   1.00    3.00    --   -6.24 -37.00   0.00   30
  3  ω    -14.00  36.00   1.00    3.00    --    3.89 -99.00  60.00   50
  4  ω    -47.00 -22.00   1.00    3.00    --   -6.24 -57.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0243067000
_diffrn_orient_matrix_UB_12      0.0207588000
_diffrn_orient_matrix_UB_13      0.0213152000
_diffrn_orient_matrix_UB_21      -0.0349898000
_diffrn_orient_matrix_UB_22      0.0179873000
_diffrn_orient_matrix_UB_23      -0.0166575000
_diffrn_orient_matrix_UB_31      -0.0230237000
_diffrn_orient_matrix_UB_32      -0.0492862000
_diffrn_orient_matrix_UB_33      0.0029032000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3755
_reflns_number_total             6056
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.016
_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)+(0.0541P)²+1.0428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1327
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26),
  C27(H27), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_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
Cl1 Cl 0.78101(5) 0.01731(5) 0.19624(2) 0.0904(2) Uani 1 1 d . . . . .
O1 O 0.58074(8) 0.64031(9) 0.49158(4) 0.0507(3) Uani 1 1 d . . . . .
C1 C 0.60875(10) 0.55298(11) 0.47829(6) 0.0407(3) Uani 1 1 d . . . . .
C2 C 0.68472(11) 0.49422(12) 0.50188(6) 0.0432(4) Uani 1 1 d . . . . .
C3 C 0.74801(13) 0.52976(15) 0.53778(7) 0.0564(4) Uani 1 1 d . . . . .
H3 H 0.743700 0.597476 0.551980 0.068 Uiso 1 1 calc R U . . .
C4 C 0.81733(14) 0.46135(16) 0.55164(8) 0.0702(6) Uani 1 1 d . . . . .
H4 H 0.860364 0.482702 0.575783 0.084 Uiso 1 1 calc R U . . .
C5 C 0.82339(14) 0.36090(16) 0.52985(8) 0.0701(6) Uani 1 1 d . . . . .
H5 H 0.871534 0.316546 0.539030 0.084 Uiso 1 1 calc R U . . .
C6 C 0.75962(13) 0.32529(14) 0.49487(7) 0.0567(5) Uani 1 1 d . . . . .
H6 H 0.763910 0.257480 0.480789 0.068 Uiso 1 1 calc R U . . .
C7 C 0.68920(11) 0.39288(12) 0.48128(6) 0.0423(3) Uani 1 1 d . . . . .
C8 C 0.61030(10) 0.37151(11) 0.44468(6) 0.0400(3) Uani 1 1 d . . . . .
H8 H 0.564099 0.329513 0.462848 0.048 Uiso 1 1 calc R U . . .
C9 C 0.57237(10) 0.48377(11) 0.43610(5) 0.0384(3) Uani 1 1 d . . . . .
C10 C 0.52020(10) 0.51931(12) 0.39717(6) 0.0405(3) Uani 1 1 d . . . . .
C11 C 0.50232(11) 0.63502(12) 0.38874(6) 0.0437(4) Uani 1 1 d . . . . .
C12 C 0.57329(13) 0.70575(14) 0.38048(7) 0.0576(4) Uani 1 1 d . . . . .
H12 H 0.633296 0.681582 0.381447 0.069 Uiso 1 1 calc R U . . .
C13 C 0.55583(17) 0.81181(16) 0.37081(8) 0.0726(6) Uani 1 1 d . . . . .
H13 H 0.604228 0.858451 0.365474 0.087 Uiso 1 1 calc R U . . .
C14 C 0.46846(17) 0.84891(16) 0.36900(8) 0.0730(6) Uani 1 1 d . . . . .
H14 H 0.457107 0.920319 0.362144 0.088 Uiso 1 1 calc R U . . .
C15 C 0.39755(16) 0.78012(16) 0.37737(8) 0.0698(6) Uani 1 1 d . . . . .
H15 H 0.337856 0.805351 0.376679 0.084 Uiso 1 1 calc R U . . .
C16 C 0.41376(13) 0.67314(15) 0.38689(7) 0.0562(4) Uani 1 1 d . . . . .
H16 H 0.364980 0.626967 0.392030 0.067 Uiso 1 1 calc R U . . .
C17 C 0.48016(11) 0.44767(13) 0.35780(6) 0.0461(4) Uani 1 1 d . . . . .
C18 C 0.48751(13) 0.47285(16) 0.30596(7) 0.0593(5) Uani 1 1 d . . . . .
H18 H 0.515640 0.535916 0.296020 0.071 Uiso 1 1 calc R U . . .
C19 C 0.45307(15) 0.4043(2) 0.26916(8) 0.0761(6) Uani 1 1 d . . . . .
H19 H 0.459884 0.420513 0.234558 0.091 Uiso 1 1 calc R U . . .
C20 C 0.40884(15) 0.3124(2) 0.28345(10) 0.0825(7) Uani 1 1 d . . . . .
H20 H 0.385790 0.266653 0.258591 0.099 Uiso 1 1 calc R U . . .
C21 C 0.39883(15) 0.28853(17) 0.33455(9) 0.0753(6) Uani 1 1 d . . . . .
H21 H 0.367592 0.227337 0.344295 0.090 Uiso 1 1 calc R U . . .
C22 C 0.43498(12) 0.35501(14) 0.37152(7) 0.0568(4) Uani 1 1 d . . . . .
H22 H 0.428952 0.337429 0.406018 0.068 Uiso 1 1 calc R U . . .
C23 C 0.64020(10) 0.31033(12) 0.39814(6) 0.0412(3) Uani 1 1 d . . . . .
H23 H 0.666892 0.349280 0.371758 0.049 Uiso 1 1 calc R U . . .
C24 C 0.63231(10) 0.20581(12) 0.39087(6) 0.0429(3) Uani 1 1 d . . . . .
C25 C 0.66739(10) 0.15752(12) 0.34257(6) 0.0425(4) Uani 1 1 d . . . . .
C26 C 0.65480(12) 0.20720(14) 0.29550(6) 0.0542(4) Uani 1 1 d . . . . .
H26 H 0.622090 0.270578 0.294177 0.065 Uiso 1 1 calc R U . . .
C27 C 0.68952(14) 0.16509(15) 0.25056(7) 0.0619(5) Uani 1 1 d . . . . .
H27 H 0.680877 0.199992 0.219469 0.074 Uiso 1 1 calc R U . . .
C28 C 0.73703(12) 0.07084(14) 0.25252(7) 0.0562(4) Uani 1 1 d . . . . .
C29 C 0.74935(14) 0.01845(14) 0.29799(7) 0.0591(5) Uani 1 1 d . . . . .
H29 H 0.781176 -0.045573 0.298834 0.071 Uiso 1 1 calc R U . . .
C30 C 0.71424(12) 0.06118(13) 0.34265(7) 0.0530(4) Uani 1 1 d . . . . .
H30 H 0.722075 0.024809 0.373413 0.064 Uiso 1 1 calc R U . . .
C31 C 0.58904(16) 0.13169(15) 0.42895(8) 0.0703(6) Uani 1 1 d . . . . .
H31A H 0.568732 0.171491 0.458250 0.105 Uiso 1 1 calc R U . . .
H31B H 0.632926 0.079430 0.439620 0.105 Uiso 1 1 calc R U . . .
H31C H 0.537779 0.096758 0.413338 0.105 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C28 1.7376(17) . ?
O1 C1 1.2218(17) . ?
C1 C2 1.470(2) . ?
C1 C9 1.500(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.384(2) . ?
C3 C4 1.378(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.382(2) . ?
C7 C8 1.522(2) . ?
C8 C9 1.533(2) . ?
C8 C23 1.501(2) . ?
C9 C10 1.346(2) . ?
C10 C11 1.494(2) . ?
C10 C17 1.486(2) . ?
C11 C12 1.384(2) . ?
C11 C16 1.383(2) . ?
C12 C13 1.380(3) . ?
C13 C14 1.362(3) . ?
C14 C15 1.368(3) . ?
C15 C16 1.387(3) . ?
C17 C18 1.392(2) . ?
C17 C22 1.386(2) . ?
C18 C19 1.384(3) . ?
C19 C20 1.375(3) . ?
C20 C21 1.373(3) . ?
C21 C22 1.381(3) . ?
C23 C24 1.332(2) . ?
C24 C25 1.489(2) . ?
C24 C31 1.501(2) . ?
C25 C26 1.389(2) . ?
C25 C30 1.391(2) . ?
C26 C27 1.382(2) . ?
C27 C28 1.374(3) . ?
C28 C29 1.368(3) . ?
C29 C30 1.381(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
O1 C1 C2 125.92(14) . . ?
O1 C1 C9 127.56(14) . . ?
C2 C1 C9 106.51(12) . . ?
C3 C2 C1 128.64(15) . . ?
C7 C2 C1 109.63(13) . . ?
C7 C2 C3 121.67(15) . . ?
C4 C3 C2 117.83(17) . . ?
C3 C4 C5 120.49(17) . . ?
C6 C5 C4 121.50(18) . . ?
C5 C6 C7 118.36(16) . . ?
C2 C7 C8 111.69(13) . . ?
C6 C7 C2 120.11(15) . . ?
C6 C7 C8 128.21(14) . . ?
C7 C8 C9 101.78(11) . . ?
C23 C8 C7 112.05(12) . . ?
C23 C8 C9 117.33(12) . . ?
C1 C9 C8 107.34(12) . . ?
C10 C9 C1 124.18(13) . . ?
C10 C9 C8 128.39(13) . . ?
C9 C10 C11 122.23(14) . . ?
C9 C10 C17 122.92(14) . . ?
C17 C10 C11 114.78(13) . . ?
C12 C11 C10 121.09(14) . . ?
C16 C11 C10 120.44(15) . . ?
C16 C11 C12 118.42(16) . . ?
C13 C12 C11 120.63(18) . . ?
C14 C13 C12 120.7(2) . . ?
C13 C14 C15 119.39(19) . . ?
C14 C15 C16 120.71(19) . . ?
C11 C16 C15 120.14(19) . . ?
C18 C17 C10 120.15(16) . . ?
C22 C17 C10 121.27(15) . . ?
C22 C17 C18 118.59(16) . . ?
C19 C18 C17 120.2(2) . . ?
C20 C19 C18 120.4(2) . . ?
C21 C20 C19 119.78(19) . . ?
C20 C21 C22 120.2(2) . . ?
C21 C22 C17 120.73(19) . . ?
C24 C23 C8 126.47(14) . . ?
C23 C24 C25 119.48(14) . . ?
C23 C24 C31 123.67(15) . . ?
C25 C24 C31 116.85(14) . . ?
C26 C25 C24 121.19(14) . . ?
C26 C25 C30 117.25(15) . . ?
C30 C25 C24 121.56(14) . . ?
C27 C26 C25 121.85(16) . . ?
C28 C27 C26 118.97(17) . . ?
C27 C28 Cl1 119.32(15) . . ?
C29 C28 Cl1 119.76(15) . . ?
C29 C28 C27 120.92(16) . . ?
C28 C29 C30 119.61(17) . . ?
C29 C30 C25 121.37(16) . . ?

_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 1.107
_oxdiff_exptl_absorpt_empirical_full_min 0.818
####################################################################### 
# 
# 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_zhuht_1118_auto
_database_code_depnum_ccdc_archive 'CCDC 2419634'
loop_
_audit_author_name
_audit_author_address
e
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-11-18
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H30 O'
_chemical_formula_sum            'C37 H30 O'
_chemical_formula_weight         490.61
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8705(4)
_cell_length_b                   11.0596(4)
_cell_length_c                   16.4847(4)
_cell_angle_alpha                80.679(2)
_cell_angle_beta                 76.457(3)
_cell_angle_gamma                81.105(3)
_cell_volume                     1366.38(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11561
_cell_measurement_temperature    302.32(10)
_cell_measurement_theta_max      76.0460
_cell_measurement_theta_min      2.7630
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (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    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15670
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.266
_diffrn_reflns_theta_min         2.781
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.32(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  16.00   1.00    0.10    --  -46.54  19.00 -30.00   30
  2  ω      2.00  28.00   1.00    0.10    --  -46.54  19.00  60.00   26
  3  ω    -30.00  -4.00   1.00    0.10    --  -46.54  40.00 108.00   26
  4  ω    -23.00  59.00   1.00    0.10    --   46.54 -57.00 -60.00   82
  5  ω    -26.00  28.00   1.00    0.10    --   46.54 -19.00-180.00   54
  6  ω     22.00  47.00   1.00    0.10    --   46.54 -40.00 -45.00   25
  7  ω     72.00 105.00   1.00    0.35    --  104.27 -94.00  90.00   33
  8  ω     74.00 111.00   1.00    0.35    --  104.27-125.00 120.00   37
  9  ω     70.00 106.00   1.00    0.35    --  104.27-105.00 141.64   36
 10  ω     37.00  66.00   1.00    0.35    --  104.27-105.00 141.64   29
 11  ω     35.00  60.00   1.00    0.35    --  104.27-125.00 120.00   25
 12  ω     34.00  62.00   1.00    0.35    --  104.27 -94.00  90.00   28
 13  ω     42.00  88.00   1.00    0.10    --   46.54-125.00 150.00   46
 14  ω     51.00 105.00   1.00    0.35    --  104.27 -94.00 -60.00   54
 15  ω     78.00 111.00   1.00    0.35    --  104.27-125.00-150.00   33
 16  ω     55.00  96.00   1.00    0.35    --  104.27 -94.00-180.00   41
 17  ω     46.00  71.00   1.00    0.35    --  104.27 -61.00 -30.00   25
 18  ω     63.00  97.00   1.00    0.35    --  104.27 -77.00   0.00   34
 19  ω     43.00  73.00   1.00    0.35    --  104.27 -61.00 120.00   30
 20  ω     41.00  68.00   1.00    0.35    --  104.27 -61.00 150.00   27
 21  ω     35.00  68.00   1.00    0.35    --  104.27 -61.00-150.00   33
 22  ω     37.00  65.00   1.00    0.35    --  104.27 -61.00-180.00   28
 23  ω     91.00 119.00   1.00    0.35    --  104.27  15.00-150.00   28
 24  ω    104.00 130.00   1.00    0.35    --  104.27  45.00-180.00   26
 25  ω    137.00 177.00   1.00    0.35    --  104.27  15.00-180.00   40
 26  ω    105.00 176.00   1.00    0.35    --  104.27  40.00 108.00   71
 27  ω     89.00 143.00   1.00    0.35    --  104.27  77.00  30.00   54
 28  ω    125.00 172.00   1.00    0.35    --  104.27  15.00-150.00   47
 29  ω     91.00 132.00   1.00    0.35    --  104.27  15.00-180.00   41
 30  ω     40.00 115.00   1.00    0.10    --   46.54  40.00 108.00   75
 31  ω    -68.00 -39.00   1.00    0.35    -- -102.00  77.00 -90.00   29
 32  ω   -102.00 -72.00   1.00    0.35    -- -102.00  77.00 -90.00   30
 33  ω    -69.00 -44.00   1.00    0.35    -- -102.00  61.00 150.00   25
 34  ω    -60.00 -31.00   1.00    0.35    -- -102.00  61.00  30.00   29
 35  ω    -69.00 -37.00   1.00    0.35    -- -102.00  61.00 -30.00   32
 36  ω   -121.00 -90.00   1.00    0.35    -- -102.00 140.00-122.17   31
 37  ω   -112.00 -37.00   1.00    0.35    -- -102.00 125.00-120.00   75
 38  ω    -74.00 -34.00   1.00    0.35    -- -102.00 125.00 -60.00   40
 39  ω   -112.00 -40.00   1.00    0.35    -- -102.00 125.00   0.00   72
 40  ω   -107.00 -42.00   1.00    0.10    --  -46.54 -40.00 -45.00   65
 41  ω   -167.00-106.00   1.00    0.35    -- -102.00 -40.00 -45.00   61
 42  ω   -172.00-127.00   1.00    0.35    -- -102.00 -61.00 120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1050717000
_diffrn_orient_matrix_UB_12      -0.1117715000
_diffrn_orient_matrix_UB_13      0.0423213000
_diffrn_orient_matrix_UB_21      -0.1667797000
_diffrn_orient_matrix_UB_22      -0.0660217000
_diffrn_orient_matrix_UB_23      0.0283122000
_diffrn_orient_matrix_UB_31      0.0478284000
_diffrn_orient_matrix_UB_32      -0.0581262000
_diffrn_orient_matrix_UB_33      -0.0825202000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4926
_reflns_number_total             5419
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0135(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.081
_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)+(0.0662P)²+0.2437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36)
2.c Fitted hexagon refined as free rotating group:
 C19(C20,C21,C22,C23,C18)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_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 0.80613(13) 0.14939(8) 0.83221(6) 0.0520(3) Uani 1 1 d . . . . .
C1 C 0.69621(17) 0.44237(11) 0.72766(8) 0.0428(3) Uani 1 1 d . . . . .
H1 H 0.718574 0.488790 0.769147 0.051 Uiso 1 1 calc R U . . .
C2 C 0.87033(17) 0.38941(11) 0.67533(8) 0.0425(3) Uani 1 1 d . . . . .
C3 C 0.99204(19) 0.45259(13) 0.61497(9) 0.0511(3) Uani 1 1 d . . . . .
H3 H 0.973115 0.538064 0.602838 0.061 Uiso 1 1 calc R U . . .
C4 C 1.1419(2) 0.38642(14) 0.57317(9) 0.0566(4) Uani 1 1 d . . . . .
H4 H 1.223556 0.428048 0.532445 0.068 Uiso 1 1 calc R U . . .
C5 C 1.1721(2) 0.25915(14) 0.59107(9) 0.0569(4) Uani 1 1 d . . . . .
H5 H 1.274166 0.216178 0.562955 0.068 Uiso 1 1 calc R U . . .
C6 C 1.05072(19) 0.19600(13) 0.65065(9) 0.0507(3) Uani 1 1 d . . . . .
H6 H 1.070226 0.110559 0.662851 0.061 Uiso 1 1 calc R U . . .
C7 C 0.89958(17) 0.26164(11) 0.69196(8) 0.0430(3) Uani 1 1 d . . . . .
C8 C 0.75101(17) 0.21089(11) 0.75762(8) 0.0435(3) Uani 1 1 d . . . . .
H8 H 0.700606 0.152652 0.733797 0.052 Uiso 1 1 calc R U . . .
C9 C 0.61639(17) 0.32449(11) 0.77247(8) 0.0427(3) Uani 1 1 d . . . . .
C10 C 0.58332(17) 0.52434(11) 0.67325(8) 0.0445(3) Uani 1 1 d . . . . .
H10 H 0.519320 0.484692 0.647003 0.053 Uiso 1 1 calc R U . . .
C11 C 0.56510(16) 0.64747(11) 0.65859(8) 0.0422(3) Uani 1 1 d . . . . .
C12 C 0.45342(17) 0.71810(11) 0.60059(8) 0.0435(3) Uani 1 1 d . . . . .
C13 C 0.4219(2) 0.84609(13) 0.59200(10) 0.0571(4) Uani 1 1 d . . . . .
H13 H 0.468782 0.888870 0.624032 0.068 Uiso 1 1 calc R U . . .
C14 C 0.3217(2) 0.91145(14) 0.53646(12) 0.0679(4) Uani 1 1 d . . . . .
H14 H 0.303643 0.997193 0.531540 0.082 Uiso 1 1 calc R U . . .
C15 C 0.2492(2) 0.85185(16) 0.48900(11) 0.0682(4) Uani 1 1 d . . . . .
H15 H 0.183171 0.896069 0.451536 0.082 Uiso 1 1 calc R U . . .
C16 C 0.2761(3) 0.72513(17) 0.49781(13) 0.0774(5) Uani 1 1 d . . . . .
H16 H 0.225430 0.682911 0.466976 0.093 Uiso 1 1 calc R U . . .
C17 C 0.3774(2) 0.66004(14) 0.55192(12) 0.0673(4) Uani 1 1 d . . . . .
H17 H 0.395494 0.574365 0.555944 0.081 Uiso 1 1 calc R U . . .
C19 C 0.58741(13) 0.74666(10) 0.78175(5) 0.0630(4) Uani 1 1 d G . . . .
H19 H 0.486931 0.712877 0.812568 0.076 Uiso 1 1 calc R U . . .
C20 C 0.66855(17) 0.82047(11) 0.81810(6) 0.0780(5) Uani 1 1 d G . . . .
H20 H 0.622351 0.836072 0.873238 0.094 Uiso 1 1 calc R U . . .
C21 C 0.81874(16) 0.87096(10) 0.77203(8) 0.0790(6) Uani 1 1 d G . . . .
H21 H 0.873020 0.920346 0.796348 0.095 Uiso 1 1 calc R U . . .
C22 C 0.88779(13) 0.84764(10) 0.68961(8) 0.0779(5) Uani 1 1 d G . . . .
H22 H 0.988271 0.881425 0.658789 0.093 Uiso 1 1 calc R U . . .
C23 C 0.80665(13) 0.77383(10) 0.65326(5) 0.0628(4) Uani 1 1 d G . . . .
H23 H 0.852853 0.758230 0.598118 0.075 Uiso 1 1 calc R U . . .
C18 C 0.65647(12) 0.72334(8) 0.69933(5) 0.0465(3) Uani 1 1 d G . . . .
C24 C 0.45288(17) 0.31832(12) 0.81834(8) 0.0441(3) Uani 1 1 d . . . . .
C25 C 0.32816(18) 0.42906(12) 0.84265(9) 0.0497(3) Uani 1 1 d . . . . .
C26 C 0.1901(2) 0.47342(15) 0.80270(13) 0.0683(4) Uani 1 1 d . . . . .
H26 H 0.177845 0.435910 0.758153 0.082 Uiso 1 1 calc R U . . .
C27 C 0.0709(3) 0.57212(18) 0.82798(18) 0.0909(7) Uani 1 1 d . . . . .
H27 H -0.019663 0.601635 0.799759 0.109 Uiso 1 1 calc R U . . .
C28 C 0.0847(3) 0.6268(2) 0.89397(18) 0.0982(7) Uani 1 1 d . . . . .
H28 H 0.002947 0.692821 0.911315 0.118 Uiso 1 1 calc R U . . .
C29 C 0.2184(4) 0.5845(2) 0.93449(16) 0.1042(8) Uani 1 1 d . . . . .
H29 H 0.227689 0.621715 0.979733 0.125 Uiso 1 1 calc R U . . .
C30 C 0.3418(3) 0.48569(19) 0.90863(12) 0.0806(5) Uani 1 1 d . . . . .
H30 H 0.433675 0.458077 0.936269 0.097 Uiso 1 1 calc R U . . .
C31 C 0.38187(17) 0.19758(12) 0.85055(8) 0.0469(3) Uani 1 1 d . . . . .
C32 C 0.3462(2) 0.12721(14) 0.79555(10) 0.0571(4) Uani 1 1 d . . . . .
H32 H 0.371319 0.153599 0.737994 0.068 Uiso 1 1 calc R U . . .
C33 C 0.2733(2) 0.01777(15) 0.82553(12) 0.0681(4) Uani 1 1 d . . . . .
H33 H 0.248999 -0.028292 0.788068 0.082 Uiso 1 1 calc R U . . .
C34 C 0.2371(2) -0.02257(16) 0.91002(13) 0.0727(5) Uani 1 1 d . . . . .
H34 H 0.188803 -0.096137 0.929916 0.087 Uiso 1 1 calc R U . . .
C35 C 0.2721(3) 0.04547(18) 0.96517(12) 0.0778(5) Uani 1 1 d . . . . .
H35 H 0.248836 0.017623 1.022549 0.093 Uiso 1 1 calc R U . . .
C36 C 0.3422(2) 0.15604(16) 0.93559(10) 0.0658(4) Uani 1 1 d . . . . .
H36 H 0.362677 0.202798 0.973625 0.079 Uiso 1 1 calc R U . . .
C37 C 0.8682(2) 0.22685(15) 0.87580(10) 0.0630(4) Uani 1 1 d . . . . .
H37A H 0.954978 0.272327 0.837339 0.095 Uiso 1 1 calc R U . . .
H37B H 0.920090 0.177669 0.919404 0.095 Uiso 1 1 calc R U . . .
H37C H 0.771826 0.283370 0.900367 0.095 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.4320(15) . ?
O1 C37 1.4077(19) . ?
C1 C2 1.5255(18) . ?
C1 C9 1.5374(16) . ?
C1 C10 1.5089(18) . ?
C2 C3 1.3896(18) . ?
C2 C7 1.3887(17) . ?
C3 C4 1.385(2) . ?
C4 C5 1.385(2) . ?
C5 C6 1.382(2) . ?
C6 C7 1.3855(19) . ?
C7 C8 1.5057(17) . ?
C8 C9 1.5256(17) . ?
C9 C24 1.3369(18) . ?
C10 C11 1.3351(17) . ?
C11 C12 1.4954(18) . ?
C11 C18 1.5059(13) . ?
C12 C13 1.3886(18) . ?
C12 C17 1.387(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.365(2) . ?
C15 C16 1.374(2) . ?
C16 C17 1.377(2) . ?
C19 C20 1.3900 . ?
C19 C18 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C23 C18 1.3900 . ?
C24 C25 1.4924(19) . ?
C24 C31 1.4966(18) . ?
C25 C26 1.386(2) . ?
C25 C30 1.372(2) . ?
C26 C27 1.376(3) . ?
C27 C28 1.360(4) . ?
C28 C29 1.359(4) . ?
C29 C30 1.396(3) . ?
C31 C32 1.386(2) . ?
C31 C36 1.380(2) . ?
C32 C33 1.388(2) . ?
C33 C34 1.368(3) . ?
C34 C35 1.368(3) . ?
C35 C36 1.388(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
C37 O1 C8 114.12(10) . . ?
C2 C1 C9 101.76(10) . . ?
C10 C1 C2 111.73(10) . . ?
C10 C1 C9 113.34(10) . . ?
C3 C2 C1 128.07(12) . . ?
C7 C2 C1 112.16(11) . . ?
C7 C2 C3 119.75(12) . . ?
C4 C3 C2 119.03(13) . . ?
C3 C4 C5 121.02(13) . . ?
C6 C5 C4 120.08(14) . . ?
C5 C6 C7 119.12(13) . . ?
C2 C7 C8 111.51(11) . . ?
C6 C7 C2 120.99(12) . . ?
C6 C7 C8 127.50(12) . . ?
O1 C8 C7 112.73(10) . . ?
O1 C8 C9 113.59(10) . . ?
C7 C8 C9 103.24(10) . . ?
C8 C9 C1 110.48(10) . . ?
C24 C9 C1 126.42(11) . . ?
C24 C9 C8 123.10(11) . . ?
C11 C10 C1 127.22(11) . . ?
C10 C11 C12 122.03(11) . . ?
C10 C11 C18 121.89(11) . . ?
C12 C11 C18 116.08(10) . . ?
C13 C12 C11 121.47(12) . . ?
C17 C12 C11 122.13(11) . . ?
C17 C12 C13 116.39(13) . . ?
C12 C13 C14 121.25(14) . . ?
C15 C14 C13 121.08(14) . . ?
C14 C15 C16 118.53(15) . . ?
C15 C16 C17 120.58(16) . . ?
C16 C17 C12 122.16(14) . . ?
C20 C19 C18 120.0 . . ?
C19 C20 C21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C21 C22 C23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C19 C18 C11 120.18(7) . . ?
C23 C18 C11 119.78(7) . . ?
C23 C18 C19 120.0 . . ?
C9 C24 C25 123.47(12) . . ?
C9 C24 C31 121.83(12) . . ?
C25 C24 C31 114.69(11) . . ?
C26 C25 C24 121.28(13) . . ?
C30 C25 C24 120.50(14) . . ?
C30 C25 C26 118.12(15) . . ?
C27 C26 C25 120.98(19) . . ?
C28 C27 C26 120.4(2) . . ?
C29 C28 C27 119.73(19) . . ?
C28 C29 C30 120.4(2) . . ?
C25 C30 C29 120.3(2) . . ?
C32 C31 C24 120.50(12) . . ?
C36 C31 C24 121.26(13) . . ?
C36 C31 C32 118.17(13) . . ?
C31 C32 C33 120.67(15) . . ?
C34 C33 C32 120.22(16) . . ?
C35 C34 C33 119.90(15) . . ?
C34 C35 C36 120.07(16) . . ?
C31 C36 C35 120.96(16) . . ?

_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.622
####################################################################### 
# 
# 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_zhu_1014_auto
_database_code_depnum_ccdc_archive 'CCDC 2419633'
loop_
_audit_author_name
_audit_author_address
d
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H24 O2'
_chemical_formula_sum            'C36 H24 O2'
_chemical_formula_weight         488.55
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   16.0351(2)
_cell_length_b                   19.3964(2)
_cell_length_c                   17.3183(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.5380(10)
_cell_angle_gamma                90
_cell_volume                     5163.56(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17039
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      75.7770
_cell_measurement_theta_min      2.6940
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20264
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.849
_diffrn_reflns_theta_min         3.669
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -25.75   0.75    1.50    -- -100.00  61.00 150.00   63
  2  ω    -54.00 -25.50   0.75    1.50    -- -100.00  45.00 150.00   38
  3  ω    -55.00 -25.75   0.75    1.50    -- -100.00  45.00 120.00   39
  4  ω    -55.00 -25.75   0.75    1.50    -- -100.00  45.00  90.00   39
  5  ω    -55.00 -25.75   0.75    1.50    -- -100.00  45.00  60.00   39
  6  ω    -45.00  31.50   0.75    0.50    --  -45.30  37.00  60.00  102
  7  ω     27.00  62.25   0.75    0.50    --   45.30  57.00  30.00   47
  8  ω     72.00 118.50   0.75    0.50    --   45.30  57.00  30.00   62
  9  ω     76.00 102.25   0.75    0.50    --   45.30 135.00  95.00   35
 10  ω     98.00 123.50   0.75    1.50    --  109.64 135.00  95.00   34
 11  ω     70.00 131.50   0.75    1.50    --  109.64 134.00 -83.00   82
 12  ω     70.00  96.25   0.75    0.50    --   45.30 134.00 -83.00   35
 13  ω    112.00 158.50   0.75    1.50    --  109.64  45.00-150.00   62
 14  ω     52.00  99.25   0.75    1.50    --  109.64 -77.00-180.00   63
 15  ω     73.00  99.25   0.75    1.50    --  109.64 -77.00-150.00   35
 16  ω     27.00  94.50   0.75    0.50    --   45.30-134.00-151.00   90
 17  ω     41.00  74.00   0.75    0.50    --   45.30-135.00  29.00   44
 18  ω     53.00  78.50   0.75    1.50    --  109.64-135.00  29.00   34
 19  ω     38.00  72.50   0.75    1.50    --  109.64 -94.00  60.00   46
 20  ω     54.00  79.50   0.75    1.50    --  109.64-134.00-151.00   34
 21  ω     68.00 111.50   0.75    1.50    --  109.64-125.00-120.00   58
 22  ω   -118.00 -65.50   0.75    1.50    -- -100.00 135.00  95.00   70
 23  ω   -115.00 -70.75   0.75    1.50    -- -100.00 134.00 -83.00   59
 24  ω   -112.00 -34.00   0.75    1.50    -- -100.00 125.00-120.00  104
 25  ω   -160.00 -91.75   0.75    1.50    -- -100.00 -94.00  90.00   91
 26  ω   -163.00 -91.75   0.75    1.50    -- -100.00 -61.00 -60.00   95
 27  ω   -139.00 -91.00   0.75    1.50    -- -100.00-134.00-151.00   64
 28  ω   -171.00 -81.75   0.75    1.50    -- -100.00-125.00-120.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462916000
_diffrn_orient_matrix_UB_12      -0.0363579000
_diffrn_orient_matrix_UB_13      -0.0797984000
_diffrn_orient_matrix_UB_21      0.0243824000
_diffrn_orient_matrix_UB_22      -0.0705994000
_diffrn_orient_matrix_UB_23      0.0409509000
_diffrn_orient_matrix_UB_31      -0.0854289000
_diffrn_orient_matrix_UB_32      -0.0004113000
_diffrn_orient_matrix_UB_33      0.0239713000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4391
_reflns_number_total             5135
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00043(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.036
_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)+(0.0762P)²+1.5336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62192(7) 0.29281(6) 0.37137(7) 0.0703(3) Uani 1 1 d . . . . .
O2 O 0.25349(7) 0.35651(6) 0.20966(6) 0.0643(3) Uani 1 1 d . . . . .
H2 H 0.284652 0.340704 0.183765 0.096 Uiso 1 1 calc R U . . .
C1 C 0.54539(10) 0.30700(8) 0.36134(8) 0.0565(3) Uani 1 1 d . . . . .
C2 C 0.50749(9) 0.37657(7) 0.35315(9) 0.0572(3) Uani 1 1 d . . . . .
C3 C 0.55148(11) 0.43874(9) 0.36721(11) 0.0708(4) Uani 1 1 d . . . . .
H3 H 0.611667 0.440357 0.377881 0.085 Uiso 1 1 calc R U . . .
C4 C 0.50406(12) 0.49800(9) 0.36500(13) 0.0819(5) Uani 1 1 d . . . . .
H4 H 0.532041 0.540489 0.373865 0.098 Uiso 1 1 calc R U . . .
C5 C 0.41438(12) 0.49450(9) 0.34955(12) 0.0765(5) Uani 1 1 d . . . . .
H5 H 0.383175 0.534851 0.349942 0.092 Uiso 1 1 calc R U . . .
C6 C 0.37023(10) 0.43245(8) 0.33358(10) 0.0656(4) Uani 1 1 d . . . . .
H6 H 0.310017 0.431200 0.322737 0.079 Uiso 1 1 calc R U . . .
C7 C 0.41689(9) 0.37203(7) 0.33394(8) 0.0556(3) Uani 1 1 d . . . . .
C8 C 0.39172(10) 0.29717(7) 0.32659(8) 0.0554(3) Uani 1 1 d . . . . .
C9 C 0.47109(10) 0.25884(8) 0.35260(8) 0.0569(3) Uani 1 1 d . . . . .
C10 C 0.47387(11) 0.18922(8) 0.36558(9) 0.0624(4) Uani 1 1 d . . . . .
C11 C 0.39227(13) 0.15391(8) 0.35118(9) 0.0689(4) Uani 1 1 d . . . . .
C12 C 0.38987(17) 0.08201(9) 0.36538(11) 0.0874(6) Uani 1 1 d . . . . .
H12 H 0.441751 0.057634 0.383236 0.105 Uiso 1 1 calc R U . . .
C13 C 0.3128(2) 0.04807(11) 0.35331(14) 0.1068(8) Uani 1 1 d . . . . .
H13 H 0.312275 0.000645 0.361028 0.128 Uiso 1 1 calc R U . . .
C14 C 0.2346(2) 0.08463(13) 0.32932(13) 0.1022(8) Uani 1 1 d . . . . .
H14 H 0.182257 0.061844 0.324133 0.123 Uiso 1 1 calc R U . . .
C15 C 0.23447(14) 0.15313(10) 0.31353(11) 0.0838(6) Uani 1 1 d . . . . .
H15 H 0.181605 0.176367 0.297419 0.101 Uiso 1 1 calc R U . . .
C16 C 0.31258(12) 0.19052(8) 0.32082(9) 0.0669(4) Uani 1 1 d . . . . .
C17 C 0.31285(10) 0.26331(8) 0.30228(9) 0.0599(4) Uani 1 1 d . . . . .
C18 C 0.22925(10) 0.30221(8) 0.25592(9) 0.0619(4) Uani 1 1 d . . . . .
C19 C 0.16357(10) 0.25754(9) 0.19268(9) 0.0646(4) Uani 1 1 d . . . . .
C20 C 0.19129(11) 0.22237(9) 0.13490(9) 0.0670(4) Uani 1 1 d . . . . .
H20 H 0.249745 0.223550 0.136532 0.080 Uiso 1 1 calc R U . . .
C21 C 0.13314(12) 0.18555(9) 0.07487(10) 0.0731(4) Uani 1 1 d . . . . .
H21 H 0.152926 0.162341 0.036493 0.088 Uiso 1 1 calc R U . . .
C22 C 0.04638(13) 0.18277(10) 0.07113(11) 0.0794(5) Uani 1 1 d . . . . .
H22 H 0.007545 0.157660 0.030814 0.095 Uiso 1 1 calc R U . . .
C23 C 0.01806(13) 0.21763(12) 0.12781(13) 0.0895(6) Uani 1 1 d . . . . .
H23 H -0.040422 0.216113 0.126047 0.107 Uiso 1 1 calc R U . . .
C24 C 0.07598(12) 0.25502(11) 0.18759(12) 0.0833(6) Uani 1 1 d . . . . .
H24 H 0.055620 0.278948 0.225113 0.100 Uiso 1 1 calc R U . . .
C25 C 0.18691(11) 0.33750(9) 0.31420(10) 0.0682(4) Uani 1 1 d . . . . .
C26 C 0.20303(15) 0.31628(11) 0.39330(11) 0.0870(6) Uani 1 1 d . . . . .
H26 H 0.241061 0.279889 0.412431 0.104 Uiso 1 1 calc R U . . .
C27 C 0.1627(2) 0.34907(14) 0.44436(14) 0.1093(8) Uani 1 1 d . . . . .
H27 H 0.174080 0.334477 0.497505 0.131 Uiso 1 1 calc R U . . .
C28 C 0.10655(18) 0.40241(14) 0.41737(15) 0.1057(8) Uani 1 1 d . . . . .
H28 H 0.079479 0.423956 0.451758 0.127 Uiso 1 1 calc R U . . .
C29 C 0.09047(14) 0.42390(12) 0.33955(14) 0.0942(6) Uani 1 1 d . . . . .
H29 H 0.052110 0.460179 0.320877 0.113 Uiso 1 1 calc R U . . .
C30 C 0.13063(12) 0.39226(11) 0.28815(12) 0.0804(5) Uani 1 1 d . . . . .
H30 H 0.119703 0.407960 0.235464 0.096 Uiso 1 1 calc R U . . .
C31 C 0.55715(12) 0.15079(8) 0.39727(9) 0.0681(4) Uani 1 1 d . . . . .
C32 C 0.59873(13) 0.11988(10) 0.34698(11) 0.0815(5) Uani 1 1 d . . . . .
H32 H 0.576017 0.125248 0.291581 0.098 Uiso 1 1 calc R U . . .
C33 C 0.67267(15) 0.08139(11) 0.37625(14) 0.0939(6) Uani 1 1 d . . . . .
H33 H 0.699323 0.060926 0.340864 0.113 Uiso 1 1 calc R U . . .
C34 C 0.70722(17) 0.07310(11) 0.45744(15) 0.1031(7) Uani 1 1 d . . . . .
H34 H 0.756448 0.045969 0.477540 0.124 Uiso 1 1 calc R U . . .
C35 C 0.6691(2) 0.10477(12) 0.50850(13) 0.1124(9) Uani 1 1 d . . . . .
H35 H 0.693867 0.100607 0.563806 0.135 Uiso 1 1 calc R U . . .
C36 C 0.59376(17) 0.14330(10) 0.47936(11) 0.0950(7) Uani 1 1 d . . . . .
H36 H 0.567849 0.164096 0.515101 0.114 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2208(18) . ?
O2 H2 0.8200 . ?
O2 C18 1.4421(18) . ?
C1 C2 1.470(2) . ?
C1 C9 1.487(2) . ?
C2 C3 1.383(2) . ?
C2 C7 1.398(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(2) . ?
C7 C8 1.5027(19) . ?
C8 C9 1.431(2) . ?
C8 C17 1.380(2) . ?
C9 C10 1.368(2) . ?
C10 C11 1.434(2) . ?
C10 C31 1.491(2) . ?
C11 C12 1.419(2) . ?
C11 C16 1.425(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.397(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.356(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.421(2) . ?
C16 C17 1.448(2) . ?
C17 C18 1.549(2) . ?
C18 C19 1.550(2) . ?
C18 C25 1.529(2) . ?
C19 C20 1.385(2) . ?
C19 C24 1.383(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.371(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(3) . ?
C25 C30 1.384(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.364(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.363(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.382(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.376(2) . ?
C31 C36 1.383(2) . ?
C32 H32 0.9300 . ?
C32 C33 1.370(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.366(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.356(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.388(3) . ?
C36 H36 0.9300 . ?

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
C18 O2 H2 109.5 . . ?
O1 C1 C2 126.29(14) . . ?
O1 C1 C9 128.06(14) . . ?
C2 C1 C9 105.63(12) . . ?
C3 C2 C1 127.38(14) . . ?
C3 C2 C7 122.69(14) . . ?
C7 C2 C1 109.77(12) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.32(15) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.00(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.62(16) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.24(14) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C8 108.47(12) . . ?
C6 C7 C2 118.03(13) . . ?
C6 C7 C8 133.10(13) . . ?
C9 C8 C7 106.38(12) . . ?
C17 C8 C7 133.34(14) . . ?
C17 C8 C9 120.27(14) . . ?
C8 C9 C1 108.69(12) . . ?
C10 C9 C1 128.00(14) . . ?
C10 C9 C8 123.31(14) . . ?
C9 C10 C11 117.21(15) . . ?
C9 C10 C31 122.55(15) . . ?
C11 C10 C31 120.17(14) . . ?
C12 C11 C10 120.51(18) . . ?
C12 C11 C16 119.21(18) . . ?
C16 C11 C10 120.27(14) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.0 . . ?
C14 C15 C16 122.1(2) . . ?
C16 C15 H15 119.0 . . ?
C11 C16 C17 120.57(14) . . ?
C15 C16 C11 116.96(16) . . ?
C15 C16 C17 122.41(18) . . ?
C8 C17 C16 117.17(15) . . ?
C8 C17 C18 120.60(13) . . ?
C16 C17 C18 122.22(13) . . ?
O2 C18 C17 108.27(11) . . ?
O2 C18 C19 104.60(12) . . ?
O2 C18 C25 106.28(13) . . ?
C17 C18 C19 114.07(13) . . ?
C25 C18 C17 110.94(13) . . ?
C25 C18 C19 112.12(12) . . ?
C20 C19 C18 119.51(13) . . ?
C24 C19 C18 122.56(14) . . ?
C24 C19 C20 117.76(15) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.79(15) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.84(16) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.92(16) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.38(17) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 121.31(17) . . ?
C19 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C26 C25 C18 121.86(18) . . ?
C26 C25 C30 118.18(17) . . ?
C30 C25 C18 119.96(15) . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.3(2) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.4(2) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 H30 119.6 . . ?
C29 C30 C25 120.7(2) . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C10 121.97(14) . . ?
C32 C31 C36 117.68(18) . . ?
C36 C31 C10 120.32(16) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 C31 121.82(18) . . ?
C33 C32 H32 119.1 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.3 . . ?
C35 C34 C33 119.5(2) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 H35 119.5 . . ?
C34 C35 C36 120.9(2) . . ?
C36 C35 H35 119.5 . . ?
C31 C36 C35 120.1(2) . . ?
C31 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -10.7(3) . . . . ?
O1 C1 C2 C7 173.71(14) . . . . ?
O1 C1 C9 C8 -168.91(14) . . . . ?
O1 C1 C9 C10 10.5(2) . . . . ?
O2 C18 C19 C20 64.81(19) . . . . ?
O2 C18 C19 C24 -110.40(18) . . . . ?
O2 C18 C25 C26 -139.08(16) . . . . ?
O2 C18 C25 C30 40.98(19) . . . . ?
C1 C2 C3 C4 -172.65(17) . . . . ?
C1 C2 C7 C6 172.16(13) . . . . ?
C1 C2 C7 C8 -1.51(16) . . . . ?
C1 C9 C10 C11 -178.70(13) . . . . ?
C1 C9 C10 C31 4.3(2) . . . . ?
C2 C1 C9 C8 9.55(14) . . . . ?
C2 C1 C9 C10 -171.01(13) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C2 C7 C8 C9 7.48(15) . . . . ?
C2 C7 C8 C17 -173.31(14) . . . . ?
C3 C2 C7 C6 -3.7(2) . . . . ?
C3 C2 C7 C8 -177.37(14) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C2 2.0(2) . . . . ?
C5 C6 C7 C8 173.79(16) . . . . ?
C6 C7 C8 C9 -164.87(16) . . . . ?
C6 C7 C8 C17 14.3(3) . . . . ?
C7 C2 C3 C4 2.4(3) . . . . ?
C7 C8 C9 C1 -10.42(14) . . . . ?
C7 C8 C9 C10 170.11(13) . . . . ?
C7 C8 C17 C16 -165.90(14) . . . . ?
C7 C8 C17 C18 15.1(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C8 C9 C10 C31 -176.32(13) . . . . ?
C8 C17 C18 O2 30.23(17) . . . . ?
C8 C17 C18 C19 146.22(13) . . . . ?
C8 C17 C18 C25 -86.02(15) . . . . ?
C9 C1 C2 C3 170.82(15) . . . . ?
C9 C1 C2 C7 -4.79(15) . . . . ?
C9 C8 C17 C16 13.23(19) . . . . ?
C9 C8 C17 C18 -165.74(12) . . . . ?
C9 C10 C11 C12 -178.28(14) . . . . ?
C9 C10 C11 C16 3.0(2) . . . . ?
C9 C10 C31 C32 -93.2(2) . . . . ?
C9 C10 C31 C36 88.9(2) . . . . ?
C10 C11 C12 C13 178.83(16) . . . . ?
C10 C11 C16 C15 -175.65(13) . . . . ?
C10 C11 C16 C17 1.5(2) . . . . ?
C10 C31 C32 C33 -176.33(18) . . . . ?
C10 C31 C36 C35 177.01(19) . . . . ?
C11 C10 C31 C32 89.9(2) . . . . ?
C11 C10 C31 C36 -88.0(2) . . . . ?
C11 C12 C13 C14 -2.3(3) . . . . ?
C11 C16 C17 C8 -9.6(2) . . . . ?
C11 C16 C17 C18 169.31(13) . . . . ?
C12 C11 C16 C15 5.6(2) . . . . ?
C12 C11 C16 C17 -177.23(13) . . . . ?
C12 C13 C14 C15 3.7(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 -4.4(2) . . . . ?
C14 C15 C16 C17 178.54(17) . . . . ?
C15 C16 C17 C8 167.35(14) . . . . ?
C15 C16 C17 C18 -13.7(2) . . . . ?
C16 C11 C12 C13 -2.4(2) . . . . ?
C16 C17 C18 O2 -148.69(13) . . . . ?
C16 C17 C18 C19 -32.70(18) . . . . ?
C16 C17 C18 C25 95.06(16) . . . . ?
C17 C8 C9 C1 170.24(12) . . . . ?
C17 C8 C9 C10 -9.2(2) . . . . ?
C17 C18 C19 C20 -53.30(19) . . . . ?
C17 C18 C19 C24 131.49(18) . . . . ?
C17 C18 C25 C26 -21.6(2) . . . . ?
C17 C18 C25 C30 158.45(14) . . . . ?
C18 C19 C20 C21 -176.07(16) . . . . ?
C18 C19 C24 C23 176.48(19) . . . . ?
C18 C25 C26 C27 -179.30(18) . . . . ?
C18 C25 C30 C29 178.73(16) . . . . ?
C19 C18 C25 C26 107.21(18) . . . . ?
C19 C18 C25 C30 -72.73(19) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C19 C24 C23 1.2(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C19 -1.0(4) . . . . ?
C24 C19 C20 C21 -0.6(3) . . . . ?
C25 C18 C19 C20 179.54(15) . . . . ?
C25 C18 C19 C24 4.3(2) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C25 C30 C29 -1.2(3) . . . . ?
C26 C27 C28 C29 -0.4(4) . . . . ?
C27 C28 C29 C30 -0.2(4) . . . . ?
C28 C29 C30 C25 1.0(3) . . . . ?
C30 C25 C26 C27 0.6(3) . . . . ?
C31 C10 C11 C12 -1.2(2) . . . . ?
C31 C10 C11 C16 -179.95(13) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C31 C36 C35 -1.0(3) . . . . ?
C32 C33 C34 C35 -1.8(4) . . . . ?
C33 C34 C35 C36 2.5(4) . . . . ?
C34 C35 C36 C31 -1.0(4) . . . . ?
C36 C31 C32 C33 1.6(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 2.869
_oxdiff_exptl_absorpt_empirical_full_min 0.347
####################################################################### 
# 
# 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_mo_1123_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2419632'
loop_
_audit_author_name
_audit_author_address
c
;Baoji University of Arts and Sciences
China
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2022-11-24
_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        ?
_chemical_formula_moiety         'C36 H26 O'
_chemical_formula_sum            'C36 H26 O'
_chemical_formula_weight         474.57
_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/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                   9.2849(7)
_cell_length_b                   21.4705(17)
_cell_length_c                   12.8615(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.362(3)
_cell_angle_gamma                90
_cell_volume                     2561.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8206
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.4094.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55086
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.392
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4233
_reflns_number_total             5242
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0612
_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)+(0.0800P)²+1.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C32(H32), C26(H26), C5(H5), C19(H19), C13(H13), C9(H9), C22(H22),
 C28(H28), C27(H27), C34(H34), C33(H33), C36(H36), C30(H30), C29(H29), C12(H12),
  C20(H20), C10(H10), C35(H35), C1(H1), C21(H21), C4(H4), C2(H2), C11(H11),
 C3(H3)
;
_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 0.63445(19) 0.14767(7) 0.13753(12) 0.0455(4) Uani 1 1 d . . . . .
C23 C 0.4261(2) 0.32645(9) 0.22805(15) 0.0284(4) Uani 1 1 d . . . . .
H23 H 0.356706 0.295335 0.210095 0.034 Uiso 1 1 calc R . . . .
C24 C 0.3748(2) 0.38083(9) 0.26141(14) 0.0274(4) Uani 1 1 d . . . . .
C32 C 0.5462(2) 0.42700(10) 0.39536(16) 0.0329(4) Uani 1 1 d . . . . .
H32 H 0.535132 0.390609 0.436268 0.039 Uiso 1 1 calc R . . . .
C31 C 0.4721(2) 0.43212(9) 0.29982(15) 0.0287(4) Uani 1 1 d . . . . .
C25 C 0.2167(2) 0.39215(9) 0.26520(15) 0.0283(4) Uani 1 1 d . . . . .
C26 C 0.1184(2) 0.36342(10) 0.19585(16) 0.0330(4) Uani 1 1 d . . . . .
H26 H 0.152390 0.336725 0.143308 0.040 Uiso 1 1 calc R . . . .
C17 C 0.6144(2) 0.30988(9) 0.10108(15) 0.0304(4) Uani 1 1 d . . . . .
C16 C 0.6319(2) 0.25003(10) 0.06279(15) 0.0322(4) Uani 1 1 d . . . . .
C18 C 0.5824(2) 0.30904(9) 0.21576(15) 0.0286(4) Uani 1 1 d . . . . .
H18 H 0.648348 0.337568 0.256604 0.034 Uiso 1 1 calc R . . . .
C14 C 0.6088(2) 0.24083(9) 0.24613(15) 0.0295(4) Uani 1 1 d . . . . .
C6 C 0.6366(2) 0.15162(10) 0.37110(16) 0.0335(4) Uani 1 1 d . . . . .
C15 C 0.6241(2) 0.20394(10) 0.14741(16) 0.0330(4) Uani 1 1 d . . . . .
C8 C 0.6438(2) 0.26181(9) 0.43501(15) 0.0318(4) Uani 1 1 d . . . . .
C5 C 0.7496(3) 0.13034(10) 0.43624(17) 0.0391(5) Uani 1 1 d . . . . .
H5 H 0.821643 0.158598 0.461444 0.047 Uiso 1 1 calc R . . . .
C19 C 0.6550(2) 0.23904(11) -0.04206(16) 0.0401(5) Uani 1 1 d . . . . .
H19 H 0.664047 0.197823 -0.067828 0.048 Uiso 1 1 calc R . . . .
C7 C 0.6276(2) 0.21884(9) 0.34363(15) 0.0304(4) Uani 1 1 d . . . . .
C13 C 0.7659(2) 0.29828(10) 0.45029(17) 0.0376(5) Uani 1 1 d . . . . .
H13 H 0.838275 0.297558 0.400206 0.045 Uiso 1 1 calc R . . . .
C9 C 0.5392(2) 0.26318(10) 0.50992(16) 0.0373(5) Uani 1 1 d . . . . .
H9 H 0.456107 0.237506 0.501839 0.045 Uiso 1 1 calc R . . . .
C22 C 0.6236(2) 0.36092(11) 0.03479(17) 0.0381(5) Uani 1 1 d . . . . .
H22 H 0.612070 0.402130 0.060042 0.046 Uiso 1 1 calc R . . . .
C28 C -0.0801(2) 0.41246(11) 0.27783(19) 0.0429(5) Uani 1 1 d . . . . .
H28 H -0.180748 0.419313 0.282013 0.052 Uiso 1 1 calc R . . . .
C27 C -0.0286(2) 0.37332(11) 0.20262(19) 0.0408(5) Uani 1 1 d . . . . .
H27 H -0.094255 0.353050 0.155213 0.049 Uiso 1 1 calc R . . . .
C34 C 0.6541(2) 0.52753(11) 0.37428(19) 0.0430(5) Uani 1 1 d . . . . .
H34 H 0.716476 0.559713 0.399425 0.052 Uiso 1 1 calc R . . . .
C33 C 0.6362(2) 0.47442(10) 0.43175(19) 0.0412(5) Uani 1 1 d . . . . .
H33 H 0.686164 0.470109 0.497310 0.049 Uiso 1 1 calc R . . . .
C36 C 0.4895(3) 0.48639(10) 0.24242(18) 0.0441(6) Uani 1 1 d . . . . .
H36 H 0.438800 0.491252 0.177236 0.053 Uiso 1 1 calc R . . . .
C30 C 0.1627(2) 0.43162(10) 0.34038(17) 0.0384(5) Uani 1 1 d . . . . .
H30 H 0.227768 0.452083 0.388016 0.046 Uiso 1 1 calc R . . . .
C29 C 0.0157(3) 0.44150(11) 0.34679(19) 0.0451(6) Uani 1 1 d . . . . .
H29 H -0.019029 0.468357 0.398836 0.054 Uiso 1 1 calc R . . . .
C12 C 0.7841(3) 0.33583(11) 0.53752(18) 0.0433(5) Uani 1 1 d . . . . .
H12 H 0.869182 0.360073 0.547458 0.052 Uiso 1 1 calc R . . . .
C20 C 0.6642(3) 0.28969(13) -0.10724(18) 0.0469(6) Uani 1 1 d . . . . .
H20 H 0.680454 0.283392 -0.178916 0.056 Uiso 1 1 calc R . . . .
C10 C 0.5557(3) 0.30178(11) 0.59605(17) 0.0448(6) Uani 1 1 d . . . . .
H10 H 0.482729 0.303426 0.645608 0.054 Uiso 1 1 calc R . . . .
C35 C 0.5803(3) 0.53353(11) 0.27972(19) 0.0487(6) Uani 1 1 d . . . . .
H35 H 0.591675 0.570224 0.239590 0.058 Uiso 1 1 calc R . . . .
C1 C 0.5304(3) 0.10978(11) 0.33759(19) 0.0422(5) Uani 1 1 d . . . . .
H1 H 0.452283 0.123728 0.293528 0.051 Uiso 1 1 calc R . . . .
C21 C 0.6499(3) 0.35000(12) -0.06920(18) 0.0457(6) Uani 1 1 d . . . . .
H21 H 0.658367 0.384313 -0.115189 0.055 Uiso 1 1 calc R . . . .
C4 C 0.7574(3) 0.06792(12) 0.46451(19) 0.0489(6) Uani 1 1 d . . . . .
H4 H 0.836382 0.053524 0.507315 0.059 Uiso 1 1 calc R . . . .
C2 C 0.5373(3) 0.04787(11) 0.3679(2) 0.0499(6) Uani 1 1 d . . . . .
H2 H 0.463425 0.019764 0.345334 0.060 Uiso 1 1 calc R . . . .
C11 C 0.6786(3) 0.33794(11) 0.60991(18) 0.0469(6) Uani 1 1 d . . . . .
H11 H 0.690195 0.364154 0.669169 0.056 Uiso 1 1 calc R . . . .
C3 C 0.6518(3) 0.02684(11) 0.4310(2) 0.0510(6) Uani 1 1 d . . . . .
H3 H 0.657256 -0.015720 0.450999 0.061 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
O1 C15 1.219(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.338(3) . ?
C23 C18 1.513(3) . ?
C24 C31 1.495(3) . ?
C24 C25 1.491(3) . ?
C32 H32 0.9500 . ?
C32 C31 1.388(3) . ?
C32 C33 1.386(3) . ?
C31 C36 1.392(3) . ?
C25 C26 1.394(3) . ?
C25 C30 1.394(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.387(3) . ?
C17 C16 1.388(3) . ?
C17 C18 1.517(3) . ?
C17 C22 1.393(3) . ?
C16 C15 1.475(3) . ?
C16 C19 1.394(3) . ?
C18 H18 1.0000 . ?
C18 C14 1.533(3) . ?
C14 C15 1.508(3) . ?
C14 C7 1.344(3) . ?
C6 C5 1.393(3) . ?
C6 C7 1.487(3) . ?
C6 C1 1.390(3) . ?
C8 C7 1.497(3) . ?
C8 C13 1.385(3) . ?
C8 C9 1.397(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.389(3) . ?
C28 H28 0.9500 . ?
C28 C27 1.381(3) . ?
C28 C29 1.379(3) . ?
C27 H27 0.9500 . ?
C34 H34 0.9500 . ?
C34 C33 1.372(3) . ?
C34 C35 1.377(4) . ?
C33 H33 0.9500 . ?
C36 H36 0.9500 . ?
C36 C35 1.390(3) . ?
C30 H30 0.9500 . ?
C30 C29 1.387(3) . ?
C29 H29 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.380(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(4) . ?
C35 H35 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.386(3) . ?
C21 H21 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(4) . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 C23 H23 116.4 . . ?
C24 C23 C18 127.19(17) . . ?
C18 C23 H23 116.4 . . ?
C23 C24 C31 122.03(17) . . ?
C23 C24 C25 121.09(17) . . ?
C25 C24 C31 116.84(16) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C33 C32 C31 120.7(2) . . ?
C32 C31 C24 120.32(18) . . ?
C32 C31 C36 118.16(19) . . ?
C36 C31 C24 121.51(18) . . ?
C26 C25 C24 121.80(18) . . ?
C26 C25 C30 117.93(18) . . ?
C30 C25 C24 120.27(17) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C16 C17 C18 111.37(17) . . ?
C16 C17 C22 120.02(19) . . ?
C22 C17 C18 128.59(19) . . ?
C17 C16 C15 110.45(17) . . ?
C17 C16 C19 121.6(2) . . ?
C19 C16 C15 127.9(2) . . ?
C23 C18 C17 109.03(15) . . ?
C23 C18 H18 111.3 . . ?
C23 C18 C14 110.72(16) . . ?
C17 C18 H18 111.3 . . ?
C17 C18 C14 102.91(15) . . ?
C14 C18 H18 111.3 . . ?
C15 C14 C18 107.87(16) . . ?
C7 C14 C18 125.91(18) . . ?
C7 C14 C15 125.99(18) . . ?
C5 C6 C7 119.65(19) . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 121.45(19) . . ?
O1 C15 C16 125.56(19) . . ?
O1 C15 C14 128.23(19) . . ?
C16 C15 C14 106.14(17) . . ?
C13 C8 C7 120.99(19) . . ?
C13 C8 C9 118.61(19) . . ?
C9 C8 C7 120.30(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C16 C19 H19 121.0 . . ?
C20 C19 C16 118.1(2) . . ?
C20 C19 H19 121.0 . . ?
C14 C7 C6 124.48(18) . . ?
C14 C7 C8 121.39(18) . . ?
C6 C7 C8 114.13(17) . . ?
C8 C13 H13 119.5 . . ?
C8 C13 C12 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C17 C22 H22 120.9 . . ?
C21 C22 C17 118.3(2) . . ?
C21 C22 H22 120.9 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C29 C28 C27 119.5(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.8 . . ?
C33 C34 H34 120.4 . . ?
C33 C34 C35 119.1(2) . . ?
C35 C34 H34 120.4 . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.9(2) . . ?
C34 C33 H33 119.6 . . ?
C31 C36 H36 119.7 . . ?
C35 C36 C31 120.5(2) . . ?
C35 C36 H36 119.7 . . ?
C25 C30 H30 119.4 . . ?
C29 C30 C25 121.1(2) . . ?
C29 C30 H30 119.4 . . ?
C28 C29 C30 120.2(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C34 C35 C36 120.6(2) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C22 C21 C20 121.2(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?

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
C23 C24 C31 C32 -72.3(3) . . . . ?
C23 C24 C31 C36 108.8(2) . . . . ?
C23 C24 C25 C26 -29.9(3) . . . . ?
C23 C24 C25 C30 149.2(2) . . . . ?
C23 C18 C14 C15 105.17(18) . . . . ?
C23 C18 C14 C7 -80.1(2) . . . . ?
C24 C23 C18 C17 -104.7(2) . . . . ?
C24 C23 C18 C14 142.8(2) . . . . ?
C24 C31 C36 C35 179.9(2) . . . . ?
C24 C25 C26 C27 178.24(19) . . . . ?
C24 C25 C30 C29 -178.4(2) . . . . ?
C32 C31 C36 C35 0.9(3) . . . . ?
C31 C24 C25 C26 152.12(19) . . . . ?
C31 C24 C25 C30 -28.9(3) . . . . ?
C31 C32 C33 C34 0.1(3) . . . . ?
C31 C36 C35 C34 -0.4(4) . . . . ?
C25 C24 C31 C32 105.7(2) . . . . ?
C25 C24 C31 C36 -73.2(3) . . . . ?
C25 C26 C27 C28 0.6(3) . . . . ?
C25 C30 C29 C28 -0.4(4) . . . . ?
C26 C25 C30 C29 0.7(3) . . . . ?
C17 C16 C15 O1 179.4(2) . . . . ?
C17 C16 C15 C14 -3.4(2) . . . . ?
C17 C16 C19 C20 1.8(3) . . . . ?
C17 C18 C14 C15 -11.2(2) . . . . ?
C17 C18 C14 C7 163.49(19) . . . . ?
C17 C22 C21 C20 1.2(3) . . . . ?
C16 C17 C18 C23 -108.09(18) . . . . ?
C16 C17 C18 C14 9.5(2) . . . . ?
C16 C17 C22 C21 0.2(3) . . . . ?
C16 C19 C20 C21 -0.4(3) . . . . ?
C18 C23 C24 C31 -4.7(3) . . . . ?
C18 C23 C24 C25 177.37(18) . . . . ?
C18 C17 C16 C15 -4.0(2) . . . . ?
C18 C17 C16 C19 176.71(18) . . . . ?
C18 C17 C22 C21 -177.9(2) . . . . ?
C18 C14 C15 O1 -173.6(2) . . . . ?
C18 C14 C15 C16 9.3(2) . . . . ?
C18 C14 C7 C6 172.76(18) . . . . ?
C18 C14 C7 C8 -8.2(3) . . . . ?
C6 C5 C4 C3 -1.8(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C15 C16 C19 C20 -177.3(2) . . . . ?
C15 C14 C7 C6 -13.5(3) . . . . ?
C15 C14 C7 C8 165.55(18) . . . . ?
C8 C13 C12 C11 -1.0(3) . . . . ?
C8 C9 C10 C11 -1.9(3) . . . . ?
C5 C6 C7 C14 130.1(2) . . . . ?
C5 C6 C7 C8 -48.9(3) . . . . ?
C5 C6 C1 C2 -0.4(3) . . . . ?
C5 C4 C3 C2 0.5(4) . . . . ?
C19 C16 C15 O1 -1.4(4) . . . . ?
C19 C16 C15 C14 175.8(2) . . . . ?
C19 C20 C21 C22 -1.1(4) . . . . ?
C7 C14 C15 O1 11.7(3) . . . . ?
C7 C14 C15 C16 -165.36(19) . . . . ?
C7 C6 C5 C4 178.5(2) . . . . ?
C7 C6 C1 C2 -177.1(2) . . . . ?
C7 C8 C13 C12 -176.84(19) . . . . ?
C7 C8 C9 C10 178.33(19) . . . . ?
C13 C8 C7 C14 -69.2(3) . . . . ?
C13 C8 C7 C6 110.0(2) . . . . ?
C13 C8 C9 C10 1.9(3) . . . . ?
C13 C12 C11 C10 1.0(3) . . . . ?
C9 C8 C7 C14 114.5(2) . . . . ?
C9 C8 C7 C6 -66.3(2) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C22 C17 C16 C15 177.57(18) . . . . ?
C22 C17 C16 C19 -1.7(3) . . . . ?
C22 C17 C18 C23 70.1(3) . . . . ?
C22 C17 C18 C14 -172.28(19) . . . . ?
C27 C28 C29 C30 0.2(4) . . . . ?
C33 C32 C31 C24 -179.75(19) . . . . ?
C33 C32 C31 C36 -0.8(3) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C30 C25 C26 C27 -0.8(3) . . . . ?
C29 C28 C27 C26 -0.3(4) . . . . ?
C35 C34 C33 C32 0.5(3) . . . . ?
C1 C6 C5 C4 1.8(3) . . . . ?
C1 C6 C7 C14 -53.2(3) . . . . ?
C1 C6 C7 C8 127.7(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
