# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_fyc-1-1
_database_code_depnum_ccdc_archive 'CCDC 2058527'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2944(5)
_cell_length_b                   11.3560(9)
_cell_length_c                   15.9573(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1321.83(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1966
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7360
_cell_measurement_theta_min      3.0580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4093
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.201
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  17.00   1.00    3.00    --  -11.59 -57.00 150.00   69
  2  ω     10.00  78.00   1.00    3.00    --   11.74  57.00 120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001815000
_diffrn_orient_matrix_UB_12      -0.0176234000
_diffrn_orient_matrix_UB_13      0.0426822000
_diffrn_orient_matrix_UB_21      -0.0064733000
_diffrn_orient_matrix_UB_22      0.0597671000
_diffrn_orient_matrix_UB_23      0.0125467000
_diffrn_orient_matrix_UB_31      -0.0969810000
_diffrn_orient_matrix_UB_32      -0.0037769000
_diffrn_orient_matrix_UB_33      -0.0007588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                2057
_reflns_number_total             2252
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.052
_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)+(0.0431P)²+0.2734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0986
_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:
 C11(H11), C14(H14), C10(H10), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.2509(2) -0.38292(17) -0.49086(11) 0.0248(5) Uani 1 1 d . . . . .
O2 O -0.1609(3) -0.47581(17) -0.73863(12) 0.0296(5) Uani 1 1 d . . . . .
C1 C -0.2196(4) -0.5357(2) -0.59709(18) 0.0217(6) Uani 1 1 d . . . . .
C6 C -0.2483(4) -0.5007(3) -0.51435(18) 0.0230(7) Uani 1 1 d . . . . .
C8 C -0.1973(4) -0.3274(2) -0.63514(18) 0.0236(7) Uani 1 1 d . . . . .
C7 C -0.2262(4) -0.3031(3) -0.55303(18) 0.0250(7) Uani 1 1 d . . . . .
C9 C -0.1903(4) -0.4476(2) -0.66460(18) 0.0235(7) Uani 1 1 d . . . . .
C2 C -0.2197(4) -0.6571(3) -0.61434(18) 0.0263(7) Uani 1 1 d . . . . .
H2 H -0.200738 -0.682937 -0.668955 0.032 Uiso 1 1 calc R U . . .
C11 C -0.3389(4) -0.1916(2) -0.74550(18) 0.0243(7) Uani 1 1 d . . . . .
H11 H -0.377280 -0.259264 -0.779314 0.029 Uiso 1 1 calc R U . . .
C17 C -0.2274(4) -0.1775(3) -0.53477(19) 0.0274(7) Uani 1 1 d . . . . .
C14 C -0.3645(4) -0.0462(3) -0.64977(19) 0.0282(7) Uani 1 1 d . . . . .
H14 H -0.423575 0.002790 -0.607015 0.034 Uiso 1 1 calc R U . . .
C10 C -0.1767(4) -0.2158(2) -0.68576(19) 0.0256(7) Uani 1 1 d . . . . .
H10 H -0.058560 -0.212502 -0.714957 0.031 Uiso 1 1 calc R U . . .
C4 C -0.2749(4) -0.6999(3) -0.4698(2) 0.0309(8) Uani 1 1 d . . . . .
H4 H -0.293422 -0.755147 -0.427593 0.037 Uiso 1 1 calc R U . . .
C5 C -0.2753(4) -0.5816(3) -0.45023(18) 0.0271(7) Uani 1 1 d . . . . .
H5 H -0.293159 -0.556519 -0.395357 0.033 Uiso 1 1 calc R U . . .
C16 C -0.1958(4) -0.1148(3) -0.61874(18) 0.0274(7) Uani 1 1 d . . . . .
H16 H -0.086336 -0.064889 -0.617097 0.033 Uiso 1 1 calc R U . . .
C12 C -0.2927(4) -0.0801(2) -0.79609(18) 0.0271(7) Uani 1 1 d . . . . .
H12A H -0.378917 -0.068676 -0.841643 0.033 Uiso 1 1 calc R U . . .
H12B H -0.169486 -0.084062 -0.818822 0.033 Uiso 1 1 calc R U . . .
C3 C -0.2472(4) -0.7377(3) -0.5518(2) 0.0314(8) Uani 1 1 d . . . . .
H3 H -0.247424 -0.817724 -0.564146 0.038 Uiso 1 1 calc R U . . .
C15 C -0.4854(4) -0.1450(3) -0.68462(19) 0.0272(7) Uani 1 1 d . . . . .
H15A H -0.593637 -0.115634 -0.713123 0.033 Uiso 1 1 calc R U . . .
H15B H -0.519741 -0.202261 -0.642365 0.033 Uiso 1 1 calc R U . . .
C13 C -0.3094(5) 0.0202(2) -0.72979(19) 0.0316(8) Uani 1 1 d . . . . .
H13A H -0.193484 0.060787 -0.722450 0.038 Uiso 1 1 calc R U . . .
H13B H -0.402538 0.076865 -0.745781 0.038 Uiso 1 1 calc R U . . .
C18 C -0.2563(5) -0.1292(3) -0.4603(2) 0.0347(8) Uani 1 1 d . . . . .
H18A H -0.286(5) -0.175(3) -0.408(2) 0.040(9) Uiso 1 1 d . . . . .
H18B H -0.262(5) -0.044(3) -0.454(2) 0.046(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.389(3) . ?
O1 C7 1.356(3) . ?
O2 C9 1.243(3) . ?
C1 C6 1.395(4) . ?
C1 C9 1.486(4) . ?
C1 C2 1.405(4) . ?
C6 C5 1.389(4) . ?
C8 C7 1.356(4) . ?
C8 C9 1.444(4) . ?
C8 C10 1.511(4) . ?
C7 C17 1.456(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(4) . ?
C11 H11 0.9800 . ?
C11 C10 1.544(4) . ?
C11 C12 1.539(4) . ?
C11 C15 1.538(4) . ?
C17 C16 1.535(4) . ?
C17 C18 1.327(4) . ?
C14 H14 0.9800 . ?
C14 C16 1.538(4) . ?
C14 C15 1.532(4) . ?
C14 C13 1.536(4) . ?
C10 H10 0.9800 . ?
C10 C16 1.574(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C4 C3 1.393(4) . ?
C5 H5 0.9300 . ?
C16 H16 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.559(4) . ?
C3 H3 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C18 H18A 1.01(3) . ?
C18 H18B 0.97(3) . ?

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 O1 C6 116.4(2) . . ?
C6 C1 C9 121.0(2) . . ?
C6 C1 C2 117.7(3) . . ?
C2 C1 C9 121.2(3) . . ?
O1 C6 C1 122.1(2) . . ?
C5 C6 O1 115.8(2) . . ?
C5 C6 C1 122.0(3) . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 C10 111.2(2) . . ?
C9 C8 C10 128.0(2) . . ?
O1 C7 C8 126.3(3) . . ?
O1 C7 C17 120.5(2) . . ?
C8 C7 C17 113.2(3) . . ?
O2 C9 C1 122.7(2) . . ?
O2 C9 C8 124.0(3) . . ?
C8 C9 C1 113.3(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C10 C11 H11 114.8 . . ?
C12 C11 H11 114.8 . . ?
C12 C11 C10 107.6(2) . . ?
C15 C11 H11 114.8 . . ?
C15 C11 C10 101.8(2) . . ?
C15 C11 C12 101.6(2) . . ?
C7 C17 C16 106.2(2) . . ?
C18 C17 C7 125.9(3) . . ?
C18 C17 C16 127.9(3) . . ?
C16 C14 H14 114.5 . . ?
C15 C14 H14 114.5 . . ?
C15 C14 C16 101.9(2) . . ?
C15 C14 C13 102.0(2) . . ?
C13 C14 H14 114.5 . . ?
C13 C14 C16 107.9(2) . . ?
C8 C10 C11 113.8(2) . . ?
C8 C10 H10 111.9 . . ?
C8 C10 C16 103.8(2) . . ?
C11 C10 H10 111.9 . . ?
C11 C10 C16 102.8(2) . . ?
C16 C10 H10 111.9 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.7 . . ?
C17 C16 C14 113.4(3) . . ?
C17 C16 C10 105.6(2) . . ?
C17 C16 H16 111.5 . . ?
C14 C16 C10 102.8(2) . . ?
C14 C16 H16 111.5 . . ?
C10 C16 H16 111.5 . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
C11 C12 C13 103.2(2) . . ?
H12A C12 H12B 109.1 . . ?
C13 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C11 C15 H15A 112.8 . . ?
C11 C15 H15B 112.8 . . ?
C14 C15 C11 94.7(2) . . ?
C14 C15 H15A 112.8 . . ?
C14 C15 H15B 112.8 . . ?
H15A C15 H15B 110.3 . . ?
C14 C13 C12 103.1(2) . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C17 C18 H18A 124.7(18) . . ?
C17 C18 H18B 121(2) . . ?
H18A C18 H18B 115(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C5 C4 179.7(2) . . . . ?
O1 C7 C17 C16 180.0(2) . . . . ?
O1 C7 C17 C18 -2.0(5) . . . . ?
C1 C6 C5 C4 -0.5(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C6 O1 C7 C8 -0.8(4) . . . . ?
C6 O1 C7 C17 179.8(2) . . . . ?
C6 C1 C9 O2 178.6(3) . . . . ?
C6 C1 C9 C8 -0.7(4) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C8 C7 C17 C16 0.5(4) . . . . ?
C8 C7 C17 C18 178.5(3) . . . . ?
C8 C10 C16 C17 -0.4(3) . . . . ?
C8 C10 C16 C14 -119.4(2) . . . . ?
C7 O1 C6 C1 0.8(4) . . . . ?
C7 O1 C6 C5 -179.5(2) . . . . ?
C7 C8 C9 O2 -178.6(3) . . . . ?
C7 C8 C9 C1 0.7(4) . . . . ?
C7 C8 C10 C11 -110.2(3) . . . . ?
C7 C8 C10 C16 0.7(3) . . . . ?
C7 C17 C16 C14 111.7(3) . . . . ?
C7 C17 C16 C10 -0.1(3) . . . . ?
C9 C1 C6 O1 0.0(4) . . . . ?
C9 C1 C6 C5 -179.8(3) . . . . ?
C9 C1 C2 C3 -179.8(3) . . . . ?
C9 C8 C7 O1 0.1(5) . . . . ?
C9 C8 C7 C17 179.5(3) . . . . ?
C9 C8 C10 C11 69.4(4) . . . . ?
C9 C8 C10 C16 -179.7(3) . . . . ?
C2 C1 C6 O1 -179.9(2) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C2 C1 C9 O2 -1.5(4) . . . . ?
C2 C1 C9 C8 179.2(3) . . . . ?
C11 C10 C16 C17 118.4(2) . . . . ?
C11 C10 C16 C14 -0.6(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C10 C8 C7 O1 179.8(3) . . . . ?
C10 C8 C7 C17 -0.8(4) . . . . ?
C10 C8 C9 O2 1.8(5) . . . . ?
C10 C8 C9 C1 -178.9(3) . . . . ?
C10 C11 C12 C13 -71.3(3) . . . . ?
C10 C11 C15 C14 55.6(3) . . . . ?
C5 C4 C3 C2 0.1(5) . . . . ?
C16 C14 C15 C11 -56.1(3) . . . . ?
C16 C14 C13 C12 72.2(3) . . . . ?
C12 C11 C10 C8 -176.6(2) . . . . ?
C12 C11 C10 C16 71.8(3) . . . . ?
C12 C11 C15 C14 -55.4(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C15 C11 C10 C8 77.1(3) . . . . ?
C15 C11 C10 C16 -34.5(3) . . . . ?
C15 C11 C12 C13 35.2(3) . . . . ?
C15 C14 C16 C17 -77.7(3) . . . . ?
C15 C14 C16 C10 35.7(3) . . . . ?
C15 C14 C13 C12 -34.7(3) . . . . ?
C13 C14 C16 C17 175.3(2) . . . . ?
C13 C14 C16 C10 -71.2(3) . . . . ?
C13 C14 C15 C11 55.3(3) . . . . ?
C18 C17 C16 C14 -66.2(4) . . . . ?
C18 C17 C16 C10 -178.0(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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.748
####################################################################### 
# 
# 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_115_10_4
_database_code_depnum_ccdc_archive 'CCDC 2058532'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-12-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H24 O2'
_chemical_formula_sum            'C32 H24 O2'
_chemical_formula_weight         440.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.4782(7)
_cell_length_b                   17.1767(9)
_cell_length_c                   12.0834(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.707(7)
_cell_angle_gamma                90
_cell_volume                     2197.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3276
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.5730
_cell_measurement_theta_min      4.1600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.811
_diffrn_reflns_theta_min         4.175
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  37.00   1.00    1.61    --   41.11 -38.00   0.00   25
  2  ω     35.00 130.00   1.00    2.00    --  107.58 -61.00 120.00   95
  3  ω     83.00 108.00   1.00    2.00    --  107.58 -95.00  30.00   25
  4  ω     79.00 122.00   1.00    2.00    --  107.58-125.00-120.00   43
  5  ω     87.00 178.00   1.00    2.00    --  107.58  30.00  30.00   91
  6  ω    109.00 170.00   1.00    2.00    --  107.58 125.00  30.00   61
  7  ω    104.00 177.00   1.00    2.00    --  107.58  45.00 -90.00   73
  8  ω    118.00 171.00   1.00    2.00    --  107.58 125.00-150.00   53
  9  ω    -95.00  -2.00   1.00    1.61    --  -41.11 125.00-150.00   93
 10  ω   -110.00 -55.00   1.00    1.61    --  -41.11 -38.00-180.00   55
 11  ω   -111.00 -30.00   1.00    1.61    --  -41.11 -57.00  90.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0260464000
_diffrn_orient_matrix_UB_12      -0.0877494000
_diffrn_orient_matrix_UB_13      0.0230005000
_diffrn_orient_matrix_UB_21      -0.1117849000
_diffrn_orient_matrix_UB_22      -0.0185859000
_diffrn_orient_matrix_UB_23      -0.1182371000
_diffrn_orient_matrix_UB_31      0.0894997000
_diffrn_orient_matrix_UB_32      0.0022917000
_diffrn_orient_matrix_UB_33      -0.0675753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3257
_reflns_number_total             4314
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.068
_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)+(0.1004P)²+0.6149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2088
_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:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C22(H22), C23(H23), C24(H24), C25(H25),
 C28(H28), C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9510(2) 0.46382(15) 0.7156(2) 0.0281(5) Uani 1 1 d . . . . .
C2 C 1.0127(3) 0.47985(17) 0.8388(2) 0.0354(6) Uani 1 1 d . . . . .
H2 H 1.036208 0.439124 0.893760 0.042 Uiso 1 1 calc R U . . .
C3 C 1.0386(3) 0.55545(18) 0.8784(3) 0.0387(7) Uani 1 1 d . . . . .
H3 H 1.079481 0.565341 0.960034 0.046 Uiso 1 1 calc R U . . .
C4 C 1.0042(3) 0.61730(17) 0.7977(3) 0.0376(7) Uani 1 1 d . . . . .
H4 H 1.021360 0.668149 0.825745 0.045 Uiso 1 1 calc R U . . .
C5 C 0.9447(2) 0.60332(16) 0.6763(3) 0.0341(6) Uani 1 1 d . . . . .
H5 H 0.922425 0.644333 0.621884 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9186(2) 0.52691(15) 0.6369(2) 0.0278(5) Uani 1 1 d . . . . .
C7 C 0.8344(2) 0.44326(14) 0.4740(2) 0.0262(5) Uani 1 1 d . . . . .
C8 C 0.8622(2) 0.37860(14) 0.5427(2) 0.0254(5) Uani 1 1 d . . . . .
O8 O 0.94466(17) 0.32577(11) 0.73888(16) 0.0333(4) Uani 1 1 d . . . . .
O9 O 0.85841(17) 0.51733(10) 0.51377(15) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.9210(2) 0.38329(15) 0.6715(2) 0.0265(5) Uani 1 1 d . . . . .
C10 C 0.7721(2) 0.42684(14) 0.3458(2) 0.0262(5) Uani 1 1 d . . . . .
C11 C 0.7682(2) 0.33860(14) 0.3341(2) 0.0247(5) Uani 1 1 d . . . . .
H11 H 0.820015 0.320649 0.290907 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8207(2) 0.30705(14) 0.4667(2) 0.0241(5) Uani 1 1 d . . . . .
H12 H 0.891338 0.271123 0.481044 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7048(2) 0.26445(14) 0.4745(2) 0.0242(5) Uani 1 1 d . . . . .
H13 H 0.706184 0.259490 0.555809 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6953(2) 0.18763(14) 0.4085(2) 0.0244(5) Uani 1 1 d . . . . .
H14 H 0.779569 0.164172 0.435422 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6555(2) 0.21364(13) 0.2754(2) 0.0234(5) Uani 1 1 d . . . . .
H15 H 0.726954 0.205246 0.251473 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6350(2) 0.30256(14) 0.2810(2) 0.0248(5) Uani 1 1 d . . . . .
H16 H 0.577854 0.325986 0.205585 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5946(2) 0.31288(14) 0.3879(2) 0.0249(5) Uani 1 1 d . . . . .
H17A H 0.596746 0.366741 0.412721 0.030 Uiso 1 1 calc R U . . .
H17B H 0.512695 0.290101 0.373613 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6000(2) 0.12484(14) 0.4158(2) 0.0286(6) Uani 1 1 d . . . . .
H18 H 0.618491 0.108700 0.498700 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4654(2) 0.15355(14) 0.3539(2) 0.0281(5) Uani 1 1 d . . . . .
C20 C 0.4351(2) 0.17307(14) 0.2338(2) 0.0269(5) Uani 1 1 d . . . . .
C21 C 0.5429(2) 0.16287(14) 0.1937(2) 0.0257(5) Uani 1 1 d . . . . .
H21 H 0.518358 0.175427 0.108617 0.031 Uiso 1 1 calc R U . . .
C22 C 0.3150(3) 0.20063(15) 0.1641(3) 0.0346(6) Uani 1 1 d . . . . .
H22 H 0.294486 0.213913 0.084201 0.042 Uiso 1 1 calc R U . . .
C23 C 0.2260(3) 0.20808(17) 0.2157(3) 0.0452(8) Uani 1 1 d . . . . .
H23 H 0.145200 0.225705 0.169308 0.054 Uiso 1 1 calc R U . . .
C24 C 0.2563(3) 0.18960(17) 0.3347(3) 0.0448(8) Uani 1 1 d . . . . .
H24 H 0.196275 0.195103 0.368284 0.054 Uiso 1 1 calc R U . . .
C25 C 0.3773(3) 0.16263(16) 0.4047(3) 0.0363(6) Uani 1 1 d . . . . .
H25 H 0.398350 0.150840 0.485241 0.044 Uiso 1 1 calc R U . . .
C26 C 0.6164(2) 0.05855(14) 0.3405(2) 0.0280(5) Uani 1 1 d . . . . .
C27 C 0.5882(2) 0.07945(14) 0.2214(2) 0.0261(5) Uani 1 1 d . . . . .
C28 C 0.6061(2) 0.02634(16) 0.1430(3) 0.0334(6) Uani 1 1 d . . . . .
H28 H 0.588422 0.040216 0.063809 0.040 Uiso 1 1 calc R U . . .
C29 C 0.6507(3) -0.04807(17) 0.1839(3) 0.0410(7) Uani 1 1 d . . . . .
H29 H 0.662599 -0.083956 0.131595 0.049 Uiso 1 1 calc R U . . .
C30 C 0.6773(3) -0.06875(16) 0.3014(3) 0.0427(7) Uani 1 1 d . . . . .
H30 H 0.705493 -0.118820 0.327452 0.051 Uiso 1 1 calc R U . . .
C31 C 0.6621(3) -0.01519(16) 0.3816(3) 0.0371(6) Uani 1 1 d . . . . .
H31 H 0.682394 -0.028696 0.461377 0.045 Uiso 1 1 calc R U . . .
C32 C 0.7259(3) 0.48043(16) 0.2616(2) 0.0347(6) Uani 1 1 d . . . . .
H32A H 0.729(3) 0.539(2) 0.276(3) 0.041(8) Uiso 1 1 d . . . . .
H32B H 0.688(3) 0.468(2) 0.178(3) 0.048(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.407(3) . ?
C1 C6 1.395(4) . ?
C1 C9 1.474(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(4) . ?
C6 O9 1.387(3) . ?
C7 C8 1.349(3) . ?
C7 O9 1.350(3) . ?
C7 C10 1.462(3) . ?
C8 C9 1.440(3) . ?
C8 C12 1.498(3) . ?
O8 C9 1.242(3) . ?
C10 C11 1.521(3) . ?
C10 C32 1.321(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.575(3) . ?
C11 C16 1.541(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.552(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.524(3) . ?
C13 C17 1.539(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.558(3) . ?
C14 C18 1.563(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.551(3) . ?
C15 C21 1.555(3) . ?
C16 H16 0.9800 . ?
C16 C17 1.542(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9800 . ?
C18 C19 1.516(4) . ?
C18 C26 1.514(3) . ?
C19 C20 1.397(3) . ?
C19 C25 1.380(4) . ?
C20 C21 1.502(3) . ?
C20 C22 1.392(4) . ?
C21 H21 0.9800 . ?
C21 C27 1.517(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.392(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.397(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.396(3) . ?
C26 C31 1.387(4) . ?
C27 C28 1.385(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.394(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.379(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.394(4) . ?
C31 H31 0.9300 . ?
C32 H32A 1.02(3) . ?
C32 H32B 0.95(3) . ?

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
C2 C1 C9 121.2(2) . . ?
C6 C1 C2 117.5(2) . . ?
C6 C1 C9 121.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 122.3(2) . . ?
O9 C6 C1 122.1(2) . . ?
O9 C6 C5 115.6(2) . . ?
C8 C7 O9 126.1(2) . . ?
C8 C7 C10 113.3(2) . . ?
O9 C7 C10 120.5(2) . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 C12 110.7(2) . . ?
C9 C8 C12 127.9(2) . . ?
C7 O9 C6 116.24(19) . . ?
C8 C9 C1 112.9(2) . . ?
O8 C9 C1 123.2(2) . . ?
O8 C9 C8 123.8(2) . . ?
C7 C10 C11 106.0(2) . . ?
C32 C10 C7 124.6(2) . . ?
C32 C10 C11 129.3(2) . . ?
C10 C11 H11 111.1 . . ?
C10 C11 C12 105.20(19) . . ?
C10 C11 C16 115.3(2) . . ?
C12 C11 H11 111.1 . . ?
C16 C11 H11 111.1 . . ?
C16 C11 C12 102.33(18) . . ?
C8 C12 C11 104.37(19) . . ?
C8 C12 H12 111.2 . . ?
C8 C12 C13 115.22(19) . . ?
C11 C12 H12 111.2 . . ?
C13 C12 C11 102.96(18) . . ?
C13 C12 H12 111.2 . . ?
C12 C13 H13 114.8 . . ?
C14 C13 C12 105.43(18) . . ?
C14 C13 H13 114.8 . . ?
C14 C13 C17 103.76(19) . . ?
C17 C13 C12 101.68(18) . . ?
C17 C13 H13 114.8 . . ?
C13 C14 H14 108.7 . . ?
C13 C14 C15 103.03(18) . . ?
C13 C14 C18 118.55(19) . . ?
C15 C14 H14 108.7 . . ?
C15 C14 C18 108.88(19) . . ?
C18 C14 H14 108.7 . . ?
C14 C15 H15 108.4 . . ?
C16 C15 C14 103.08(18) . . ?
C16 C15 H15 108.4 . . ?
C16 C15 C21 118.5(2) . . ?
C21 C15 C14 109.56(18) . . ?
C21 C15 H15 108.4 . . ?
C11 C16 C15 105.72(19) . . ?
C11 C16 H16 115.0 . . ?
C11 C16 C17 100.14(19) . . ?
C15 C16 H16 115.0 . . ?
C17 C16 C15 104.46(18) . . ?
C17 C16 H16 115.0 . . ?
C13 C17 C16 94.22(18) . . ?
C13 C17 H17A 112.9 . . ?
C13 C17 H17B 112.9 . . ?
C16 C17 H17A 112.9 . . ?
C16 C17 H17B 112.9 . . ?
H17A C17 H17B 110.3 . . ?
C14 C18 H18 111.9 . . ?
C19 C18 C14 110.5(2) . . ?
C19 C18 H18 111.9 . . ?
C26 C18 C14 103.47(19) . . ?
C26 C18 H18 111.9 . . ?
C26 C18 C19 106.7(2) . . ?
C20 C19 C18 112.9(2) . . ?
C25 C19 C18 126.9(2) . . ?
C25 C19 C20 120.3(3) . . ?
C19 C20 C21 113.6(2) . . ?
C22 C20 C19 120.1(2) . . ?
C22 C20 C21 126.3(2) . . ?
C15 C21 H21 112.0 . . ?
C20 C21 C15 108.44(19) . . ?
C20 C21 H21 112.0 . . ?
C20 C21 C27 107.11(19) . . ?
C27 C21 C15 105.07(19) . . ?
C27 C21 H21 112.0 . . ?
C20 C22 H22 120.4 . . ?
C20 C22 C23 119.2(3) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C19 C25 C24 119.8(3) . . ?
C19 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C18 113.2(2) . . ?
C31 C26 C18 126.1(2) . . ?
C31 C26 C27 120.6(2) . . ?
C26 C27 C21 113.2(2) . . ?
C28 C27 C21 126.9(2) . . ?
C28 C27 C26 119.9(2) . . ?
C27 C28 H28 120.2 . . ?
C27 C28 C29 119.5(3) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.5(3) . . ?
C31 C30 H30 119.7 . . ?
C26 C31 C30 119.1(3) . . ?
C26 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C10 C32 H32A 125.6(18) . . ?
C10 C32 H32B 123(2) . . ?
H32A C32 H32B 111(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C6 O9 C7 -0.9(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 O9 179.5(2) . . . . ?
C2 C1 C9 C8 -177.8(2) . . . . ?
C2 C1 C9 O8 2.0(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 O9 179.9(2) . . . . ?
C5 C6 O9 C7 178.9(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C6 C1 C9 C8 2.5(3) . . . . ?
C6 C1 C9 O8 -177.7(2) . . . . ?
C7 C8 C9 C1 -2.7(3) . . . . ?
C7 C8 C9 O8 177.6(2) . . . . ?
C7 C8 C12 C11 3.5(3) . . . . ?
C7 C8 C12 C13 -108.7(2) . . . . ?
C7 C10 C11 C12 5.6(2) . . . . ?
C7 C10 C11 C16 117.5(2) . . . . ?
C8 C7 O9 C6 0.8(3) . . . . ?
C8 C7 C10 C11 -3.8(3) . . . . ?
C8 C7 C10 C32 173.8(3) . . . . ?
C8 C12 C13 C14 -170.4(2) . . . . ?
C8 C12 C13 C17 81.6(2) . . . . ?
O9 C7 C8 C9 1.1(4) . . . . ?
O9 C7 C8 C12 179.7(2) . . . . ?
O9 C7 C10 C11 176.6(2) . . . . ?
O9 C7 C10 C32 -5.8(4) . . . . ?
C9 C1 C2 C3 -179.2(2) . . . . ?
C9 C1 C6 C5 179.3(2) . . . . ?
C9 C1 C6 O9 -0.9(4) . . . . ?
C9 C8 C12 C11 -178.0(2) . . . . ?
C9 C8 C12 C13 69.8(3) . . . . ?
C10 C7 C8 C9 -178.5(2) . . . . ?
C10 C7 C8 C12 0.1(3) . . . . ?
C10 C7 O9 C6 -179.6(2) . . . . ?
C10 C11 C12 C8 -5.5(2) . . . . ?
C10 C11 C12 C13 115.2(2) . . . . ?
C10 C11 C16 C15 178.72(19) . . . . ?
C10 C11 C16 C17 -73.0(2) . . . . ?
C11 C12 C13 C14 76.7(2) . . . . ?
C11 C12 C13 C17 -31.3(2) . . . . ?
C11 C16 C17 C13 -59.2(2) . . . . ?
C12 C8 C9 C1 179.0(2) . . . . ?
C12 C8 C9 O8 -0.8(4) . . . . ?
C12 C11 C16 C15 -67.7(2) . . . . ?
C12 C11 C16 C17 40.6(2) . . . . ?
C12 C13 C14 C15 -68.7(2) . . . . ?
C12 C13 C14 C18 171.0(2) . . . . ?
C12 C13 C17 C16 55.5(2) . . . . ?
C13 C14 C15 C16 -5.1(2) . . . . ?
C13 C14 C15 C21 -132.1(2) . . . . ?
C13 C14 C18 C19 65.8(3) . . . . ?
C13 C14 C18 C26 179.7(2) . . . . ?
C14 C13 C17 C16 -53.8(2) . . . . ?
C14 C15 C16 C11 76.1(2) . . . . ?
C14 C15 C16 C17 -29.0(2) . . . . ?
C14 C15 C21 C20 59.4(2) . . . . ?
C14 C15 C21 C27 -54.8(2) . . . . ?
C14 C18 C19 C20 57.7(3) . . . . ?
C14 C18 C19 C25 -121.1(3) . . . . ?
C14 C18 C26 C27 -60.6(3) . . . . ?
C14 C18 C26 C31 115.4(3) . . . . ?
C15 C14 C18 C19 -51.4(2) . . . . ?
C15 C14 C18 C26 62.5(2) . . . . ?
C15 C16 C17 C13 50.1(2) . . . . ?
C15 C21 C27 C26 62.0(2) . . . . ?
C15 C21 C27 C28 -116.1(3) . . . . ?
C16 C11 C12 C8 -126.38(19) . . . . ?
C16 C11 C12 C13 -5.7(2) . . . . ?
C16 C15 C21 C20 -58.3(3) . . . . ?
C16 C15 C21 C27 -172.61(19) . . . . ?
C17 C13 C14 C15 37.8(2) . . . . ?
C17 C13 C14 C18 -82.5(2) . . . . ?
C18 C14 C15 C16 121.6(2) . . . . ?
C18 C14 C15 C21 -5.4(3) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C18 C19 C20 C22 -179.9(2) . . . . ?
C18 C19 C25 C24 -179.7(2) . . . . ?
C18 C26 C27 C21 -2.2(3) . . . . ?
C18 C26 C27 C28 176.1(2) . . . . ?
C18 C26 C31 C30 -176.9(3) . . . . ?
C19 C18 C26 C27 56.0(3) . . . . ?
C19 C18 C26 C31 -128.1(3) . . . . ?
C19 C20 C21 C15 -57.7(3) . . . . ?
C19 C20 C21 C27 55.2(3) . . . . ?
C19 C20 C22 C23 -0.3(4) . . . . ?
C20 C19 C25 C24 1.6(4) . . . . ?
C20 C21 C27 C26 -53.2(3) . . . . ?
C20 C21 C27 C28 128.7(3) . . . . ?
C20 C22 C23 C24 1.0(4) . . . . ?
C21 C15 C16 C11 -162.72(19) . . . . ?
C21 C15 C16 C17 92.1(2) . . . . ?
C21 C20 C22 C23 -178.8(2) . . . . ?
C21 C27 C28 C29 178.8(2) . . . . ?
C22 C20 C21 C15 120.8(3) . . . . ?
C22 C20 C21 C27 -126.2(3) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C19 -0.9(4) . . . . ?
C25 C19 C20 C21 177.6(2) . . . . ?
C25 C19 C20 C22 -1.0(4) . . . . ?
C26 C18 C19 C20 -54.2(3) . . . . ?
C26 C18 C19 C25 127.1(3) . . . . ?
C26 C27 C28 C29 0.8(4) . . . . ?
C27 C26 C31 C30 -1.2(4) . . . . ?
C27 C28 C29 C30 -0.2(4) . . . . ?
C28 C29 C30 C31 -1.2(4) . . . . ?
C29 C30 C31 C26 1.9(4) . . . . ?
C31 C26 C27 C21 -178.4(2) . . . . ?
C31 C26 C27 C28 -0.1(4) . . . . ?
C32 C10 C11 C12 -171.8(3) . . . . ?
C32 C10 C11 C16 -59.9(4) . . . . ?

_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 2.252
_oxdiff_exptl_absorpt_empirical_full_min 0.366
####################################################################### 
# 
# 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_p122
_database_code_depnum_ccdc_archive 'CCDC 2058534'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-11-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 O2'
_chemical_formula_sum            'C24 H20 O2'
_chemical_formula_weight         340.40
_chemical_absolute_configuration unk
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9952(5)
_cell_length_b                   16.7750(15)
_cell_length_c                   8.7581(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.597(10)
_cell_angle_gamma                90
_cell_volume                     844.10(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1285
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.7940
_cell_measurement_theta_min      2.6890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3430
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.427
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00   1.00   1.00    4.50    --  -11.27 -37.00-180.00   86
  2  ω    -37.00  60.00   1.00    4.50    --  -11.27  57.00 -30.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1155782000
_diffrn_orient_matrix_UB_12      -0.0050620000
_diffrn_orient_matrix_UB_13      -0.0492340000
_diffrn_orient_matrix_UB_21      -0.0367422000
_diffrn_orient_matrix_UB_22      -0.0098475000
_diffrn_orient_matrix_UB_23      0.0678957000
_diffrn_orient_matrix_UB_31      -0.0232750000
_diffrn_orient_matrix_UB_32      0.0407827000
_diffrn_orient_matrix_UB_33      0.0101517000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.691
_reflns_Friedel_fraction_max     0.691
_reflns_number_gt                2160
_reflns_number_total             2523
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.038
_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)+(0.0451P)²+0.0388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1063
_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:
 C11(H11), C10(H10), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C5(H5), C21(H21), C20(H20), C2(H2), C22(H22), C18(H18),
 C4(H4), C3(H3)
;
_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
O001 O 0.5449(5) 0.42593(16) 0.7185(3) 0.0223(7) Uani 1 1 d . . . . .
O002 O 0.1877(5) 0.34287(18) 0.2700(3) 0.0312(8) Uani 1 1 d . . . . .
C1 C 0.2299(7) 0.3465(2) 0.5497(5) 0.0189(9) Uani 1 1 d . . . . .
C12 C 0.7982(7) 0.4990(2) 0.5940(4) 0.0175(9) Uani 1 1 d . . . . .
C19 C 1.0930(7) 0.6000(2) 0.7516(4) 0.0181(9) Uani 1 1 d . . . . .
C6 C 0.3530(7) 0.3767(3) 0.6980(5) 0.0195(10) Uani 1 1 d . . . . .
C9 C 0.2978(7) 0.3668(3) 0.4031(5) 0.0210(10) Uani 1 1 d . . . . .
C23 C 1.2846(7) 0.7141(3) 0.9049(5) 0.0241(10) Uani 1 1 d . . . . .
H23 H 1.294343 0.750821 0.986024 0.029 Uiso 1 1 calc R U . . .
C24 C 1.1139(7) 0.6554(3) 0.8735(5) 0.0232(10) Uani 1 1 d . . . . .
H24 H 1.011087 0.653086 0.935251 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2856(7) 0.3609(3) 0.8348(5) 0.0235(10) Uani 1 1 d . . . . .
H5 H 0.370430 0.381673 0.932672 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5022(7) 0.4169(2) 0.4360(5) 0.0189(9) Uani 1 1 d . . . . .
C11 C 0.8218(7) 0.5038(2) 0.4244(4) 0.0195(10) Uani 1 1 d . . . . .
H11 H 0.976445 0.486463 0.420992 0.023 Uiso 1 1 calc R U . . .
C21 C 1.4233(7) 0.6629(3) 0.6937(5) 0.0242(11) Uani 1 1 d . . . . .
H21 H 1.527907 0.665063 0.633140 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6084(7) 0.4437(2) 0.5847(5) 0.0184(9) Uani 1 1 d . . . . .
C20 C 1.2517(7) 0.6049(3) 0.6616(5) 0.0206(10) Uani 1 1 d . . . . .
H20 H 1.241794 0.568727 0.579363 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0349(8) 0.2985(2) 0.5423(5) 0.0248(11) Uani 1 1 d . . . . .
H2 H -0.049481 0.276905 0.445183 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6254(7) 0.4478(3) 0.3210(5) 0.0205(9) Uani 1 1 d . . . . .
H10 H 0.692004 0.404076 0.274024 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7582(7) 0.5861(3) 0.3446(4) 0.0197(9) Uani 1 1 d . . . . .
H13 H 0.820560 0.631866 0.413121 0.024 Uiso 1 1 calc R U . . .
C22 C 1.4409(7) 0.7175(3) 0.8144(5) 0.0226(10) Uani 1 1 d . . . . .
H22 H 1.556350 0.756347 0.835108 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4910(7) 0.5819(3) 0.2855(5) 0.0205(9) Uani 1 1 d . . . . .
H14A H 0.420476 0.576011 0.371744 0.025 Uiso 1 1 calc R U . . .
H14B H 0.422722 0.626896 0.218876 0.025 Uiso 1 1 calc R U . . .
C18 C 0.9081(7) 0.5393(3) 0.7265(5) 0.0200(10) Uani 1 1 d . . . . .
H18 H 0.860369 0.527210 0.815910 0.024 Uiso 1 1 calc R U . . .
C17 C 0.8191(7) 0.5845(3) 0.1858(5) 0.0262(10) Uani 1 1 d . . . . .
H17A H 0.975845 0.564683 0.200316 0.031 Uiso 1 1 calc R U . . .
H17B H 0.805740 0.637149 0.138327 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0932(8) 0.3146(3) 0.8238(5) 0.0296(11) Uani 1 1 d . . . . .
H4 H 0.046320 0.304190 0.914292 0.035 Uiso 1 1 calc R U . . .
C15 C 0.4835(7) 0.5053(3) 0.1907(4) 0.0217(10) Uani 1 1 d . . . . .
H15 H 0.326536 0.486664 0.134693 0.026 Uiso 1 1 calc R U . . .
C3 C -0.0328(8) 0.2829(3) 0.6766(6) 0.0297(11) Uani 1 1 d . . . . .
H3 H -0.162597 0.251200 0.669668 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6354(7) 0.5265(3) 0.0816(5) 0.0264(11) Uani 1 1 d . . . . .
H16A H 0.544279 0.552376 -0.015193 0.032 Uiso 1 1 calc R U . . .
H16B H 0.708950 0.479384 0.053664 0.032 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
O001 C6 1.386(5) . ?
O001 C7 1.364(4) . ?
O002 C9 1.231(5) . ?
C1 C6 1.393(5) . ?
C1 C9 1.493(5) . ?
C1 C2 1.407(6) . ?
C12 C11 1.534(5) . ?
C12 C7 1.452(5) . ?
C12 C18 1.342(6) . ?
C19 C24 1.394(6) . ?
C19 C20 1.400(5) . ?
C19 C18 1.474(6) . ?
C6 C5 1.395(5) . ?
C9 C8 1.446(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(6) . ?
C23 C22 1.390(6) . ?
C24 H24 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.372(6) . ?
C8 C7 1.353(5) . ?
C8 C10 1.501(6) . ?
C11 H11 0.9800 . ?
C11 C10 1.574(6) . ?
C11 C13 1.546(6) . ?
C21 H21 0.9300 . ?
C21 C20 1.386(6) . ?
C21 C22 1.381(6) . ?
C20 H20 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.374(6) . ?
C10 H10 0.9800 . ?
C10 C15 1.550(6) . ?
C13 H13 0.9800 . ?
C13 C14 1.538(5) . ?
C13 C17 1.536(5) . ?
C22 H22 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.524(6) . ?
C18 H18 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.555(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.399(6) . ?
C15 H15 0.9800 . ?
C15 C16 1.538(5) . ?
C3 H3 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 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 O001 C6 116.4(3) . . ?
C6 C1 C9 121.2(4) . . ?
C6 C1 C2 117.6(4) . . ?
C2 C1 C9 121.2(4) . . ?
C7 C12 C11 105.5(3) . . ?
C18 C12 C11 130.7(4) . . ?
C18 C12 C7 123.6(3) . . ?
C24 C19 C20 117.7(4) . . ?
C24 C19 C18 118.3(3) . . ?
C20 C19 C18 124.0(4) . . ?
O001 C6 C1 122.4(3) . . ?
O001 C6 C5 115.8(4) . . ?
C1 C6 C5 121.7(4) . . ?
O002 C9 C1 122.4(4) . . ?
O002 C9 C8 124.9(4) . . ?
C8 C9 C1 112.7(4) . . ?
C24 C23 H23 120.2 . . ?
C24 C23 C22 119.7(4) . . ?
C22 C23 H23 120.2 . . ?
C19 C24 H24 119.2 . . ?
C23 C24 C19 121.6(4) . . ?
C23 C24 H24 119.2 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
C9 C8 C10 128.2(4) . . ?
C7 C8 C9 121.6(4) . . ?
C7 C8 C10 110.2(4) . . ?
C12 C11 H11 111.4 . . ?
C12 C11 C10 105.4(3) . . ?
C12 C11 C13 113.9(3) . . ?
C10 C11 H11 111.4 . . ?
C13 C11 H11 111.4 . . ?
C13 C11 C10 103.0(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C22 C21 C20 120.7(4) . . ?
O001 C7 C12 119.9(3) . . ?
C8 C7 O001 125.7(4) . . ?
C8 C7 C12 114.3(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C8 C10 C11 104.5(3) . . ?
C8 C10 H10 111.1 . . ?
C8 C10 C15 115.9(3) . . ?
C11 C10 H10 111.1 . . ?
C15 C10 C11 102.4(3) . . ?
C15 C10 H10 111.1 . . ?
C11 C13 H13 114.9 . . ?
C14 C13 C11 102.1(3) . . ?
C14 C13 H13 114.9 . . ?
C17 C13 C11 107.5(3) . . ?
C17 C13 H13 114.9 . . ?
C17 C13 C14 100.9(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 C23 119.5(4) . . ?
C21 C22 H22 120.2 . . ?
C13 C14 H14A 112.7 . . ?
C13 C14 H14B 112.7 . . ?
H14A C14 H14B 110.2 . . ?
C15 C14 C13 95.0(3) . . ?
C15 C14 H14A 112.7 . . ?
C15 C14 H14B 112.7 . . ?
C12 C18 C19 129.8(4) . . ?
C12 C18 H18 115.1 . . ?
C19 C18 H18 115.1 . . ?
C13 C17 H17A 111.1 . . ?
C13 C17 H17B 111.1 . . ?
C13 C17 C16 103.3(3) . . ?
H17A C17 H17B 109.1 . . ?
C16 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C10 C15 H15 114.6 . . ?
C14 C15 C10 101.5(3) . . ?
C14 C15 H15 114.6 . . ?
C14 C15 C16 102.3(3) . . ?
C16 C15 C10 107.7(3) . . ?
C16 C15 H15 114.6 . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
C15 C16 C17 103.0(3) . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C6 C5 C4 178.1(4) . . . . ?
O002 C9 C8 C7 177.1(4) . . . . ?
O002 C9 C8 C10 -1.9(7) . . . . ?
C1 C6 C5 C4 0.0(6) . . . . ?
C1 C9 C8 C7 -2.6(6) . . . . ?
C1 C9 C8 C10 178.4(4) . . . . ?
C1 C2 C3 C4 -0.3(7) . . . . ?
C12 C11 C10 C8 1.2(4) . . . . ?
C12 C11 C10 C15 122.4(3) . . . . ?
C12 C11 C13 C14 -81.2(4) . . . . ?
C12 C11 C13 C17 173.1(3) . . . . ?
C6 O001 C7 C12 176.1(3) . . . . ?
C6 O001 C7 C8 -0.7(6) . . . . ?
C6 C1 C9 O002 -177.8(4) . . . . ?
C6 C1 C9 C8 1.9(5) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C6 C5 C4 C3 0.6(6) . . . . ?
C9 C1 C6 O001 -0.7(6) . . . . ?
C9 C1 C6 C5 177.3(4) . . . . ?
C9 C1 C2 C3 -177.1(4) . . . . ?
C9 C8 C7 O001 2.2(6) . . . . ?
C9 C8 C7 C12 -174.7(4) . . . . ?
C9 C8 C10 C11 175.8(4) . . . . ?
C9 C8 C10 C15 63.9(6) . . . . ?
C24 C19 C20 C21 0.1(6) . . . . ?
C24 C19 C18 C12 154.2(4) . . . . ?
C24 C23 C22 C21 0.4(6) . . . . ?
C5 C4 C3 C2 -0.4(7) . . . . ?
C8 C10 C15 C14 75.7(4) . . . . ?
C8 C10 C15 C16 -177.3(4) . . . . ?
C11 C12 C7 O001 179.4(3) . . . . ?
C11 C12 C7 C8 -3.5(5) . . . . ?
C11 C12 C18 C19 -2.0(8) . . . . ?
C11 C10 C15 C14 -37.4(4) . . . . ?
C11 C10 C15 C16 69.6(4) . . . . ?
C11 C13 C14 C15 -54.9(3) . . . . ?
C11 C13 C17 C16 69.8(4) . . . . ?
C7 O001 C6 C1 0.0(5) . . . . ?
C7 O001 C6 C5 -178.1(3) . . . . ?
C7 C12 C11 C10 1.1(4) . . . . ?
C7 C12 C11 C13 113.3(4) . . . . ?
C7 C12 C18 C19 -176.4(4) . . . . ?
C7 C8 C10 C11 -3.3(5) . . . . ?
C7 C8 C10 C15 -115.2(4) . . . . ?
C20 C19 C24 C23 0.4(6) . . . . ?
C20 C19 C18 C12 -26.6(7) . . . . ?
C20 C21 C22 C23 0.1(6) . . . . ?
C2 C1 C6 O001 -178.7(4) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
C2 C1 C9 O002 0.1(6) . . . . ?
C2 C1 C9 C8 179.8(4) . . . . ?
C10 C8 C7 O001 -178.7(4) . . . . ?
C10 C8 C7 C12 4.4(5) . . . . ?
C10 C11 C13 C14 32.4(4) . . . . ?
C10 C11 C13 C17 -73.3(4) . . . . ?
C10 C15 C16 C17 -73.8(4) . . . . ?
C13 C11 C10 C8 -118.5(3) . . . . ?
C13 C11 C10 C15 2.8(4) . . . . ?
C13 C14 C15 C10 56.7(3) . . . . ?
C13 C14 C15 C16 -54.5(3) . . . . ?
C13 C17 C16 C15 2.8(4) . . . . ?
C22 C23 C24 C19 -0.7(6) . . . . ?
C22 C21 C20 C19 -0.4(6) . . . . ?
C14 C13 C17 C16 -36.8(4) . . . . ?
C14 C15 C16 C17 32.7(4) . . . . ?
C18 C12 C11 C10 -174.0(4) . . . . ?
C18 C12 C11 C13 -61.8(6) . . . . ?
C18 C12 C7 O001 -5.0(6) . . . . ?
C18 C12 C7 C8 172.1(4) . . . . ?
C18 C19 C24 C23 179.7(4) . . . . ?
C18 C19 C20 C21 -179.0(4) . . . . ?
C17 C13 C14 C15 56.0(4) . . . . ?

_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 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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_15-1
_database_code_depnum_ccdc_archive 'CCDC 2058528'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-11-21
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 O2'
_chemical_formula_sum            'C18 H14 O2'
_chemical_formula_weight         262.29
_chemical_absolute_configuration unk
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.3438(6)
_cell_length_b                   14.9294(15)
_cell_length_c                   8.1896(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.718(11)
_cell_angle_gamma                90
_cell_volume                     645.82(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1681
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.5770
_cell_measurement_theta_min      3.8390
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3087
_diffrn_reflns_point_group_measured_fraction_full 0.794
_diffrn_reflns_point_group_measured_fraction_max 0.628
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.449
_diffrn_reflns_theta_min         2.516
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  92.00   1.00    1.00    --   12.05  19.00 150.00  115
  2  ω     37.00  99.00   1.00    1.00    --   12.05-178.00  30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0381609000
_diffrn_orient_matrix_UB_12      0.0321011000
_diffrn_orient_matrix_UB_13      0.0552070000
_diffrn_orient_matrix_UB_21      -0.0596534000
_diffrn_orient_matrix_UB_22      0.0255109000
_diffrn_orient_matrix_UB_23      -0.0680016000
_diffrn_orient_matrix_UB_31      -0.1139892000
_diffrn_orient_matrix_UB_32      -0.0240558000
_diffrn_orient_matrix_UB_33      0.0016366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.435
_reflns_Friedel_fraction_full    0.570
_reflns_Friedel_fraction_max     0.395
_reflns_number_gt                2076
_reflns_number_total             2260
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.044
_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)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4(15)
 0.6(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9675(3) 0.38560(11) 0.44805(19) 0.0353(4) Uani 1 1 d . . . . .
O2 O 0.6157(3) 0.48511(11) 0.00181(18) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.9406(4) 0.39066(14) 0.1549(3) 0.0236(5) Uani 1 1 d . . . . .
C2 C 1.1461(5) 0.33376(16) 0.1472(3) 0.0289(5) Uani 1 1 d . . . . .
H2 H 1.232147 0.309317 0.244203 0.035 Uiso 1 1 calc R U . . .
C3 C 1.2240(5) 0.31309(17) -0.0016(3) 0.0327(6) Uani 1 1 d . . . . .
H3 H 1.361562 0.275300 -0.004719 0.039 Uiso 1 1 calc R U . . .
C4 C 1.0940(5) 0.34955(17) -0.1477(3) 0.0319(6) Uani 1 1 d . . . . .
H4 H 1.146635 0.336130 -0.248096 0.038 Uiso 1 1 calc R U . . .
C5 C 0.8902(5) 0.40474(16) -0.1446(3) 0.0300(5) Uani 1 1 d . . . . .
H5 H 0.802285 0.427738 -0.242337 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8157(4) 0.42612(15) 0.0070(3) 0.0250(5) Uani 1 1 d . . . . .
C7 C 0.5508(4) 0.51011(15) 0.1488(3) 0.0244(5) Uani 1 1 d . . . . .
C8 C 0.6620(4) 0.48076(15) 0.2988(3) 0.0222(5) Uani 1 1 d . . . . .
C9 C 0.8641(4) 0.41645(15) 0.3158(3) 0.0244(5) Uani 1 1 d . . . . .
C10 C 0.5446(4) 0.52542(16) 0.4337(3) 0.0237(5) Uani 1 1 d . . . . .
H10 H 0.472898 0.481720 0.502972 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3359(4) 0.58811(15) 0.3388(3) 0.0258(5) Uani 1 1 d . . . . .
H11 H 0.167807 0.572728 0.364372 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4200(4) 0.68329(17) 0.4064(3) 0.0280(5) Uani 1 1 d . . . . .
H12 H 0.343585 0.734227 0.341622 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7098(4) 0.67465(16) 0.4213(3) 0.0268(5) Uani 1 1 d . . . . .
H13A H 0.799019 0.726697 0.471576 0.032 Uiso 1 1 calc R U . . .
H13B H 0.766086 0.660644 0.317079 0.032 Uiso 1 1 calc R U . . .
C14 C 0.7232(4) 0.59356(15) 0.5391(3) 0.0239(5) Uani 1 1 d . . . . .
H14 H 0.893346 0.571775 0.582524 0.029 Uiso 1 1 calc R U . . .
C15 C 0.5695(4) 0.62987(16) 0.6656(3) 0.0287(5) Uani 1 1 d . . . . .
H15 H 0.596327 0.617440 0.778217 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3901(4) 0.68240(18) 0.5876(3) 0.0312(5) Uani 1 1 d . . . . .
H16 H 0.268169 0.713130 0.635345 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3494(4) 0.57461(15) 0.1568(3) 0.0258(5) Uani 1 1 d . . . . .
C18 C 0.2052(5) 0.61232(19) 0.0289(3) 0.0367(6) Uani 1 1 d . . . . .
H18A H 0.075(5) 0.6576(18) 0.051(3) 0.035(7) Uiso 1 1 d . . . . .
H18B H 0.218(5) 0.5959(19) -0.088(3) 0.039(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.228(3) . ?
O2 C6 1.381(3) . ?
O2 C7 1.354(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.396(3) . ?
C1 C9 1.488(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(3) . ?
C7 C8 1.354(3) . ?
C7 C17 1.453(3) . ?
C8 C9 1.436(3) . ?
C8 C10 1.506(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.569(3) . ?
C10 C14 1.563(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.566(3) . ?
C11 C17 1.517(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.541(3) . ?
C12 C16 1.517(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.543(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.517(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.325(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.328(3) . ?
C18 H18A 1.01(3) . ?
C18 H18B 1.00(3) . ?

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 O2 C6 116.73(17) . . ?
C2 C1 C9 121.4(2) . . ?
C6 C1 C2 117.8(2) . . ?
C6 C1 C9 120.7(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
O2 C6 C1 122.3(2) . . ?
O2 C6 C5 116.24(19) . . ?
C1 C6 C5 121.4(2) . . ?
O2 C7 C17 120.91(19) . . ?
C8 C7 O2 125.5(2) . . ?
C8 C7 C17 113.6(2) . . ?
C7 C8 C9 121.7(2) . . ?
C7 C8 C10 110.4(2) . . ?
C9 C8 C10 127.99(19) . . ?
O1 C9 C1 122.4(2) . . ?
O1 C9 C8 124.6(2) . . ?
C8 C9 C1 112.99(19) . . ?
C8 C10 H10 111.9 . . ?
C8 C10 C11 104.17(17) . . ?
C8 C10 C14 113.95(18) . . ?
C11 C10 H10 111.9 . . ?
C14 C10 H10 111.9 . . ?
C14 C10 C11 102.37(17) . . ?
C10 C11 H11 111.1 . . ?
C12 C11 C10 102.84(18) . . ?
C12 C11 H11 111.1 . . ?
C17 C11 C10 105.75(18) . . ?
C17 C11 H11 111.1 . . ?
C17 C11 C12 114.46(19) . . ?
C11 C12 H12 116.1 . . ?
C13 C12 C11 100.56(19) . . ?
C13 C12 H12 116.1 . . ?
C16 C12 C11 105.71(19) . . ?
C16 C12 H12 116.1 . . ?
C16 C12 C13 100.08(18) . . ?
C12 C13 H13A 113.0 . . ?
C12 C13 H13B 113.0 . . ?
C12 C13 C14 93.80(17) . . ?
H13A C13 H13B 110.4 . . ?
C14 C13 H13A 113.0 . . ?
C14 C13 H13B 113.0 . . ?
C10 C14 H14 116.1 . . ?
C13 C14 C10 101.45(17) . . ?
C13 C14 H14 116.1 . . ?
C15 C14 C10 105.15(17) . . ?
C15 C14 C13 99.67(18) . . ?
C15 C14 H14 116.1 . . ?
C14 C15 H15 126.0 . . ?
C16 C15 C14 108.0(2) . . ?
C16 C15 H15 126.0 . . ?
C12 C16 H16 126.2 . . ?
C15 C16 C12 107.5(2) . . ?
C15 C16 H16 126.2 . . ?
C7 C17 C11 106.15(18) . . ?
C18 C17 C7 126.2(2) . . ?
C18 C17 C11 127.6(2) . . ?
C17 C18 H18A 118.5(14) . . ?
C17 C18 H18B 122.3(16) . . ?
H18A C18 H18B 119(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
O2 C7 C8 C9 -1.3(3) . . . . ?
O2 C7 C8 C10 178.3(2) . . . . ?
O2 C7 C17 C11 -178.32(18) . . . . ?
O2 C7 C17 C18 2.7(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 O2 -178.0(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C1 C9 O1 -4.0(3) . . . . ?
C2 C1 C9 C8 175.34(19) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C4 C5 C6 O2 177.3(2) . . . . ?
C4 C5 C6 C1 -1.6(4) . . . . ?
C6 O2 C7 C8 -1.4(3) . . . . ?
C6 O2 C7 C17 177.59(18) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C1 C9 O1 179.0(2) . . . . ?
C6 C1 C9 C8 -1.7(3) . . . . ?
C7 O2 C6 C1 2.4(3) . . . . ?
C7 O2 C6 C5 -176.5(2) . . . . ?
C7 C8 C9 O1 -178.0(2) . . . . ?
C7 C8 C9 C1 2.7(3) . . . . ?
C7 C8 C10 C11 0.4(2) . . . . ?
C7 C8 C10 C14 -110.3(2) . . . . ?
C8 C7 C17 C11 0.8(3) . . . . ?
C8 C7 C17 C18 -178.2(2) . . . . ?
C8 C10 C11 C12 -120.32(19) . . . . ?
C8 C10 C11 C17 0.0(2) . . . . ?
C8 C10 C14 C13 76.6(2) . . . . ?
C8 C10 C14 C15 -179.91(18) . . . . ?
C9 C1 C2 C3 -177.0(2) . . . . ?
C9 C1 C6 O2 -0.9(3) . . . . ?
C9 C1 C6 C5 178.0(2) . . . . ?
C9 C8 C10 C11 179.9(2) . . . . ?
C9 C8 C10 C14 69.2(3) . . . . ?
C10 C8 C9 O1 2.6(4) . . . . ?
C10 C8 C9 C1 -176.8(2) . . . . ?
C10 C11 C12 C13 37.5(2) . . . . ?
C10 C11 C12 C16 -66.3(2) . . . . ?
C10 C11 C17 C7 -0.5(2) . . . . ?
C10 C11 C17 C18 178.5(2) . . . . ?
C10 C14 C15 C16 -71.0(2) . . . . ?
C11 C10 C14 C13 -35.2(2) . . . . ?
C11 C10 C14 C15 68.3(2) . . . . ?
C11 C12 C13 C14 -58.0(2) . . . . ?
C11 C12 C16 C15 70.9(2) . . . . ?
C12 C11 C17 C7 112.0(2) . . . . ?
C12 C11 C17 C18 -69.0(3) . . . . ?
C12 C13 C14 C10 57.52(19) . . . . ?
C12 C13 C14 C15 -50.2(2) . . . . ?
C13 C12 C16 C15 -33.2(2) . . . . ?
C13 C14 C15 C16 33.7(2) . . . . ?
C14 C10 C11 C12 -1.4(2) . . . . ?
C14 C10 C11 C17 118.98(18) . . . . ?
C14 C15 C16 C12 -0.4(3) . . . . ?
C16 C12 C13 C14 50.2(2) . . . . ?
C17 C7 C8 C9 179.7(2) . . . . ?
C17 C7 C8 C10 -0.8(3) . . . . ?
C17 C11 C12 C13 -76.7(2) . . . . ?
C17 C11 C12 C16 179.56(18) . . . . ?

_olex2_date_sample_data_collection 2020-11-21
_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.598
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4(15)
2 0.6(15)

####################################################################### 
# 
# 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_115-09
_database_code_depnum_ccdc_archive 'CCDC 2058530'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-11-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 O2'
_chemical_formula_sum            'C26 H22 O2'
_chemical_formula_weight         366.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.0214(6)
_cell_length_b                   15.4607(9)
_cell_length_c                   11.2885(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.746(5)
_cell_angle_gamma                90
_cell_volume                     1901.18(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3490
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.0290
_cell_measurement_theta_min      2.6340
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8636
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.251
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  21.00   1.00    3.00    --  -11.43 -19.00 -90.00  111
  2  ω     -9.00  83.00   1.00    3.00    --   12.05  77.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0381697000
_diffrn_orient_matrix_UB_12      0.0360715000
_diffrn_orient_matrix_UB_13      -0.0182136000
_diffrn_orient_matrix_UB_21      0.0201533000
_diffrn_orient_matrix_UB_22      0.0203374000
_diffrn_orient_matrix_UB_23      0.0557470000
_diffrn_orient_matrix_UB_31      0.0488379000
_diffrn_orient_matrix_UB_32      0.0197180000
_diffrn_orient_matrix_UB_33      -0.0244046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2718
_reflns_number_total             3347
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.055
_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)+(0.0406P)²+0.6026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1038
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.95537(13) -0.27970(8) -0.30842(13) 0.0473(4) Uani 1 1 d . . . . .
O2 O -0.87356(10) -0.52868(7) -0.40043(10) 0.0230(3) Uani 1 1 d . . . . .
C1 C -0.97481(14) -0.43082(10) -0.27828(14) 0.0231(4) Uani 1 1 d . . . . .
C2 C -1.04826(15) -0.42322(11) -0.18807(16) 0.0292(4) Uani 1 1 d . . . . .
H2 H -1.068922 -0.368534 -0.163221 0.035 Uiso 1 1 calc R U . . .
C3 C -1.09041(16) -0.49517(12) -0.13553(16) 0.0303(4) Uani 1 1 d . . . . .
H3 H -1.139674 -0.488986 -0.076099 0.036 Uiso 1 1 calc R U . . .
C4 C -1.05932(15) -0.57709(11) -0.17132(15) 0.0259(4) Uani 1 1 d . . . . .
H4 H -1.087451 -0.625666 -0.135201 0.031 Uiso 1 1 calc R U . . .
C5 C -0.98726(14) -0.58702(11) -0.25977(14) 0.0230(4) Uani 1 1 d . . . . .
H5 H -0.966653 -0.641926 -0.283840 0.028 Uiso 1 1 calc R U . . .
C6 C -0.94591(13) -0.51408(10) -0.31239(14) 0.0203(4) Uani 1 1 d . . . . .
C7 C -0.83091(14) -0.45773(10) -0.45125(14) 0.0219(4) Uani 1 1 d . . . . .
C8 C -0.85520(14) -0.37487(10) -0.42625(14) 0.0223(4) Uani 1 1 d . . . . .
C9 C -0.93044(15) -0.35390(11) -0.33592(16) 0.0273(4) Uani 1 1 d . . . . .
C10 C -0.79142(14) -0.31397(11) -0.50035(14) 0.0238(4) Uani 1 1 d . . . . .
H10 H -0.850034 -0.277829 -0.552499 0.029 Uiso 1 1 calc R U . . .
C11 C -0.71820(14) -0.37577(11) -0.57477(14) 0.0243(4) Uani 1 1 d . . . . .
H11 H -0.741581 -0.366027 -0.661007 0.029 Uiso 1 1 calc R U . . .
C12 C -0.58355(15) -0.34904(11) -0.53291(14) 0.0240(4) Uani 1 1 d . . . . .
H12 H -0.522415 -0.392555 -0.546312 0.029 Uiso 1 1 calc R U . . .
C13 C -0.56794(15) -0.26091(11) -0.59070(15) 0.0278(4) Uani 1 1 d . . . . .
H13 H -0.592579 -0.258612 -0.677790 0.033 Uiso 1 1 calc R U . . .
C14 C -0.64092(15) -0.19754(11) -0.51541(15) 0.0259(4) Uani 1 1 d . . . . .
H14 H -0.702883 -0.160956 -0.562696 0.031 Uiso 1 1 calc R U . . .
C15 C -0.68932(14) -0.25924(10) -0.42689(14) 0.0215(4) Uani 1 1 d . . . . .
H15 H -0.712702 -0.231315 -0.355763 0.026 Uiso 1 1 calc R U . . .
C16 C -0.58523(14) -0.32578(11) -0.40086(14) 0.0226(4) Uani 1 1 d . . . . .
H16A H -0.606871 -0.374509 -0.354138 0.027 Uiso 1 1 calc R U . . .
H16B H -0.508707 -0.300248 -0.362896 0.027 Uiso 1 1 calc R U . . .
C17 C -0.45464(15) -0.20859(11) -0.54252(14) 0.0264(4) Uani 1 1 d . . . . .
C18 C -0.51716(15) -0.15465(11) -0.47463(14) 0.0255(4) Uani 1 1 d . . . . .
C19 C -0.45957(16) -0.09216(11) -0.39776(15) 0.0276(4) Uani 1 1 d . . . . .
C20 C -0.33201(16) -0.08903(12) -0.39593(16) 0.0319(4) Uani 1 1 d . . . . .
H20 H -0.286914 -0.048690 -0.346321 0.038 Uiso 1 1 calc R U . . .
C21 C -0.26985(16) -0.14294(12) -0.46422(16) 0.0330(4) Uani 1 1 d . . . . .
H21 H -0.185093 -0.137343 -0.457933 0.040 Uiso 1 1 calc R U . . .
C22 C -0.32902(16) -0.20561(12) -0.54246(15) 0.0299(4) Uani 1 1 d . . . . .
C23 C -0.26261(18) -0.26216(13) -0.61885(19) 0.0438(5) Uani 1 1 d . . . . .
H23A H -0.307227 -0.315167 -0.635809 0.066 Uiso 1 1 calc R U . . .
H23B H -0.181969 -0.274695 -0.577174 0.066 Uiso 1 1 calc R U . . .
H23C H -0.255981 -0.232912 -0.692614 0.066 Uiso 1 1 calc R U . . .
C24 C -0.52562(18) -0.03404(12) -0.32249(17) 0.0367(5) Uani 1 1 d . . . . .
H24A H -0.540526 0.020900 -0.361633 0.055 Uiso 1 1 calc R U . . .
H24B H -0.476185 -0.025865 -0.245645 0.055 Uiso 1 1 calc R U . . .
H24C H -0.602432 -0.059934 -0.311998 0.055 Uiso 1 1 calc R U . . .
C25 C -0.74982(14) -0.46710(11) -0.54078(14) 0.0236(4) Uani 1 1 d . . . . .
C26 C -0.71306(17) -0.54103(13) -0.58260(17) 0.0310(4) Uani 1 1 d . . . . .
H26A H -0.7393(17) -0.5985(13) -0.5536(16) 0.038(5) Uiso 1 1 d . . . . .
H26B H -0.6573(18) -0.5424(12) -0.6434(17) 0.039(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.230(2) . ?
O2 C6 1.3840(18) . ?
O2 C7 1.3548(18) . ?
C1 C2 1.399(2) . ?
C1 C6 1.394(2) . ?
C1 C9 1.474(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C7 C8 1.347(2) . ?
C7 C25 1.455(2) . ?
C8 C9 1.446(2) . ?
C8 C10 1.503(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.574(2) . ?
C10 C15 1.545(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.544(2) . ?
C11 C25 1.518(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.532(2) . ?
C12 C16 1.536(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.593(2) . ?
C13 C17 1.517(2) . ?
C14 H14 0.9800 . ?
C14 C15 1.535(2) . ?
C14 C18 1.524(2) . ?
C15 H15 0.9800 . ?
C15 C16 1.536(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.385(2) . ?
C17 C22 1.385(2) . ?
C18 C19 1.386(2) . ?
C19 C20 1.404(2) . ?
C19 C24 1.499(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.403(3) . ?
C22 C23 1.495(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.323(2) . ?
C26 H26A 1.00(2) . ?
C26 H26B 0.989(19) . ?

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 O2 C6 116.55(12) . . ?
C2 C1 C9 121.40(15) . . ?
C6 C1 C2 117.41(15) . . ?
C6 C1 C9 121.19(14) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.14(16) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.89(15) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.55(16) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.00(15) . . ?
C6 C5 H5 120.5 . . ?
O2 C6 C1 121.98(14) . . ?
O2 C6 C5 116.02(14) . . ?
C5 C6 C1 122.00(14) . . ?
O2 C7 C25 120.20(14) . . ?
C8 C7 O2 126.04(14) . . ?
C8 C7 C25 113.76(15) . . ?
C7 C8 C9 120.97(15) . . ?
C7 C8 C10 110.76(14) . . ?
C9 C8 C10 128.25(15) . . ?
O1 C9 C1 122.62(15) . . ?
O1 C9 C8 124.13(16) . . ?
C8 C9 C1 113.25(14) . . ?
C8 C10 H10 111.7 . . ?
C8 C10 C11 103.77(13) . . ?
C8 C10 C15 114.11(13) . . ?
C11 C10 H10 111.7 . . ?
C15 C10 H10 111.7 . . ?
C15 C10 C11 103.20(12) . . ?
C10 C11 H11 111.0 . . ?
C12 C11 C10 102.78(12) . . ?
C12 C11 H11 111.0 . . ?
C25 C11 C10 105.89(12) . . ?
C25 C11 H11 111.0 . . ?
C25 C11 C12 114.75(14) . . ?
C11 C12 H12 114.9 . . ?
C13 C12 C11 105.83(13) . . ?
C13 C12 H12 114.9 . . ?
C13 C12 C16 102.93(13) . . ?
C16 C12 C11 101.94(12) . . ?
C16 C12 H12 114.9 . . ?
C12 C13 H13 115.3 . . ?
C12 C13 C14 102.79(12) . . ?
C14 C13 H13 115.3 . . ?
C17 C13 C12 117.47(14) . . ?
C17 C13 H13 115.3 . . ?
C17 C13 C14 86.31(12) . . ?
C13 C14 H14 115.5 . . ?
C15 C14 C13 102.64(13) . . ?
C15 C14 H14 115.5 . . ?
C18 C14 C13 85.83(12) . . ?
C18 C14 H14 115.5 . . ?
C18 C14 C15 117.24(13) . . ?
C10 C15 H15 114.9 . . ?
C14 C15 C10 106.73(13) . . ?
C14 C15 H15 114.9 . . ?
C14 C15 C16 102.56(12) . . ?
C16 C15 C10 101.41(13) . . ?
C16 C15 H15 114.9 . . ?
C12 C16 H16A 112.7 . . ?
C12 C16 H16B 112.7 . . ?
C15 C16 C12 95.17(13) . . ?
C15 C16 H16A 112.7 . . ?
C15 C16 H16B 112.7 . . ?
H16A C16 H16B 110.2 . . ?
C18 C17 C13 93.89(13) . . ?
C18 C17 C22 124.13(16) . . ?
C22 C17 C13 141.80(16) . . ?
C17 C18 C14 93.94(13) . . ?
C17 C18 C19 123.17(15) . . ?
C19 C18 C14 142.76(16) . . ?
C18 C19 C20 113.29(16) . . ?
C18 C19 C24 123.84(16) . . ?
C20 C19 C24 122.86(16) . . ?
C19 C20 H20 118.3 . . ?
C21 C20 C19 123.37(16) . . ?
C21 C20 H20 118.3 . . ?
C20 C21 H21 118.5 . . ?
C20 C21 C22 122.95(16) . . ?
C22 C21 H21 118.5 . . ?
C17 C22 C21 113.09(16) . . ?
C17 C22 C23 123.86(16) . . ?
C21 C22 C23 123.05(16) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 C11 105.78(14) . . ?
C26 C25 C7 125.99(16) . . ?
C26 C25 C11 128.23(15) . . ?
C25 C26 H26A 121.9(10) . . ?
C25 C26 H26B 121.5(11) . . ?
H26A C26 H26B 116.6(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 C9 1.7(2) . . . . ?
O2 C7 C8 C10 179.87(14) . . . . ?
O2 C7 C25 C11 -178.49(13) . . . . ?
O2 C7 C25 C26 1.7(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C1 C6 O2 -179.78(14) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C1 C9 O1 -0.1(3) . . . . ?
C2 C1 C9 C8 179.56(15) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 O2 179.81(14) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C6 O2 C7 C8 -1.9(2) . . . . ?
C6 O2 C7 C25 177.31(14) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C1 C9 O1 179.35(17) . . . . ?
C6 C1 C9 C8 -1.0(2) . . . . ?
C7 O2 C6 C1 0.7(2) . . . . ?
C7 O2 C6 C5 -178.98(13) . . . . ?
C7 C8 C9 O1 179.54(17) . . . . ?
C7 C8 C9 C1 -0.1(2) . . . . ?
C7 C8 C10 C11 -1.69(17) . . . . ?
C7 C8 C10 C15 -113.24(16) . . . . ?
C8 C7 C25 C11 0.83(18) . . . . ?
C8 C7 C25 C26 -178.97(17) . . . . ?
C8 C10 C11 C12 -118.63(13) . . . . ?
C8 C10 C11 C25 2.10(15) . . . . ?
C8 C10 C15 C14 -176.44(13) . . . . ?
C8 C10 C15 C16 76.56(15) . . . . ?
C9 C1 C2 C3 179.32(16) . . . . ?
C9 C1 C6 O2 0.7(2) . . . . ?
C9 C1 C6 C5 -179.64(15) . . . . ?
C9 C8 C10 C11 176.35(15) . . . . ?
C9 C8 C10 C15 64.8(2) . . . . ?
C10 C8 C9 O1 1.7(3) . . . . ?
C10 C8 C9 C1 -178.00(15) . . . . ?
C10 C11 C12 C13 -73.07(15) . . . . ?
C10 C11 C12 C16 34.24(15) . . . . ?
C10 C11 C25 C7 -1.81(16) . . . . ?
C10 C11 C25 C26 177.98(17) . . . . ?
C10 C15 C16 C12 55.59(13) . . . . ?
C11 C10 C15 C14 71.67(15) . . . . ?
C11 C10 C15 C16 -35.32(15) . . . . ?
C11 C12 C13 C14 73.12(14) . . . . ?
C11 C12 C13 C17 165.63(14) . . . . ?
C11 C12 C16 C15 -55.40(14) . . . . ?
C12 C11 C25 C7 110.80(15) . . . . ?
C12 C11 C25 C26 -69.4(2) . . . . ?
C12 C13 C14 C15 -0.89(15) . . . . ?
C12 C13 C14 C18 116.11(13) . . . . ?
C12 C13 C17 C18 -101.15(16) . . . . ?
C12 C13 C17 C22 73.5(3) . . . . ?
C13 C12 C16 C15 54.15(14) . . . . ?
C13 C14 C15 C10 -71.24(14) . . . . ?
C13 C14 C15 C16 34.94(15) . . . . ?
C13 C14 C18 C17 1.35(12) . . . . ?
C13 C14 C18 C19 -174.0(2) . . . . ?
C13 C17 C18 C14 -1.42(13) . . . . ?
C13 C17 C18 C19 175.20(16) . . . . ?
C13 C17 C22 C21 -172.4(2) . . . . ?
C13 C17 C22 C23 8.5(3) . . . . ?
C14 C13 C17 C18 1.36(12) . . . . ?
C14 C13 C17 C22 176.0(2) . . . . ?
C14 C15 C16 C12 -54.64(14) . . . . ?
C14 C18 C19 C20 174.5(2) . . . . ?
C14 C18 C19 C24 -4.8(3) . . . . ?
C15 C10 C11 C12 0.68(15) . . . . ?
C15 C10 C11 C25 121.40(13) . . . . ?
C15 C14 C18 C17 103.43(16) . . . . ?
C15 C14 C18 C19 -71.9(3) . . . . ?
C16 C12 C13 C14 -33.47(15) . . . . ?
C16 C12 C13 C17 59.03(17) . . . . ?
C17 C13 C14 C15 -118.23(13) . . . . ?
C17 C13 C14 C18 -1.23(11) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C17 C18 C19 C24 -179.18(16) . . . . ?
C18 C14 C15 C10 -163.06(14) . . . . ?
C18 C14 C15 C16 -56.88(18) . . . . ?
C18 C17 C22 C21 1.2(2) . . . . ?
C18 C17 C22 C23 -178.00(17) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C17 -1.0(3) . . . . ?
C20 C21 C22 C23 178.21(17) . . . . ?
C22 C17 C18 C14 -177.41(16) . . . . ?
C22 C17 C18 C19 -0.8(3) . . . . ?
C24 C19 C20 C21 179.37(17) . . . . ?
C25 C7 C8 C9 -177.60(14) . . . . ?
C25 C7 C8 C10 0.60(19) . . . . ?
C25 C11 C12 C13 172.49(13) . . . . ?
C25 C11 C12 C16 -80.20(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 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# 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_p121
_database_code_depnum_ccdc_archive 'CCDC 2058537'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-11-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N O3'
_chemical_formula_sum            'C27 H23 N O3'
_chemical_formula_weight         409.46
_chemical_absolute_configuration unk
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           9
_space_group_name_H-M_alt        'I a '
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   12.9830(7)
_cell_length_b                   10.0352(4)
_cell_length_c                   16.4235(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.296(5)
_cell_angle_gamma                90
_cell_volume                     2019.56(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4527
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6690
_cell_measurement_theta_min      5.2890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3985
_diffrn_reflns_point_group_measured_fraction_full 0.757
_diffrn_reflns_point_group_measured_fraction_max 0.724
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.755
_diffrn_reflns_theta_min         5.251
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  36.00   1.00    1.00    --  -40.73  19.00 150.00  107
  2  ω     35.00 130.00   1.00    1.19    --  107.58 -61.00  90.00   95
  3  ω     91.00 117.00   1.00    1.19    --  107.58  45.00-120.00   26
  4  ω    138.00 178.00   1.00    1.19    --  107.58  45.00-120.00   40
  5  ω     34.00 136.00   1.00    1.19    --  107.58 -77.00-120.00  102
  6  ω   -114.00 -83.00   1.00    1.00    --  -40.98 -38.00 -30.00   31
  7  ω     12.00 114.00   1.00    1.00    --   40.98  77.00   0.00  102
  8  ω     85.00 110.00   1.00    1.00    --  107.58 -95.00   0.00   25
  9  ω     81.00 121.00   1.00    1.00    --  107.58-125.00-120.00   40
 10  ω     91.00 160.00   1.00    1.00    --  107.58 -15.00-180.00   69
 11  ω     87.00 119.00   1.00    1.00    --  107.58  45.00-150.00   32
 12  ω     41.00  66.00   1.00    1.00    --  107.58 -15.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002745045
_diffrn_orient_matrix_UB_12      -0.0412138955
_diffrn_orient_matrix_UB_13      -0.0902850045
_diffrn_orient_matrix_UB_21      0.1243264544
_diffrn_orient_matrix_UB_22      -0.0220434456
_diffrn_orient_matrix_UB_23      0.0364540456
_diffrn_orient_matrix_UB_31      -0.0188602019
_diffrn_orient_matrix_UB_32      -0.1462172019
_diffrn_orient_matrix_UB_33      0.0199592019
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.480
_reflns_Friedel_fraction_full    0.515
_reflns_Friedel_fraction_max     0.470
_reflns_number_gt                2906
_reflns_number_total             2967
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2967
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0392
_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)+(0.0752P)²+0.2223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1043
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.0(3)
 1.0(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C23(H23), C24(H24), C25(H25), C26(H26)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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 -0.47935(16) -0.21507(18) -0.42320(12) 0.0287(4) Uani 1 1 d . . . . .
O2 O -0.54827(14) -0.52819(17) -0.59559(10) 0.0221(4) Uani 1 1 d . . . . .
O3 O -0.52332(16) -0.91187(18) -0.36579(13) 0.0323(4) Uani 1 1 d . . . . .
N1 N -0.36805(19) -0.9035(2) -0.40506(15) 0.0291(5) Uani 1 1 d . . . . .
C1 C -0.48355(18) -0.3019(2) -0.55900(15) 0.0199(5) Uani 1 1 d . . . . .
C2 C -0.4399(2) -0.1870(2) -0.58320(16) 0.0247(5) Uani 1 1 d . . . . .
H2 H -0.422915 -0.114014 -0.546271 0.030 Uiso 1 1 calc R U . . .
C3 C -0.4217(2) -0.1809(3) -0.66116(17) 0.0279(5) Uani 1 1 d . . . . .
H3 H -0.391327 -0.104777 -0.676160 0.033 Uiso 1 1 calc R U . . .
C4 C -0.4491(2) -0.2897(3) -0.71785(16) 0.0293(6) Uani 1 1 d . . . . .
H4 H -0.437672 -0.284836 -0.770773 0.035 Uiso 1 1 calc R U . . .
C5 C -0.4930(2) -0.4043(3) -0.69556(16) 0.0266(5) Uani 1 1 d . . . . .
H5 H -0.511967 -0.476268 -0.733270 0.032 Uiso 1 1 calc R U . . .
C6 C -0.50823(19) -0.4095(2) -0.61580(15) 0.0205(5) Uani 1 1 d . . . . .
C7 C -0.55631(18) -0.5378(2) -0.51596(15) 0.0196(4) Uani 1 1 d . . . . .
C8 C -0.53887(18) -0.4377(2) -0.45762(14) 0.0192(5) Uani 1 1 d . . . . .
C9 C -0.50043(19) -0.3102(2) -0.47416(15) 0.0210(5) Uani 1 1 d . . . . .
C10 C -0.5617(2) -0.4841(2) -0.37804(15) 0.0214(5) Uani 1 1 d . . . . .
H10 H -0.497193 -0.477018 -0.326195 0.026 Uiso 1 1 calc R U . . .
C11 C -0.59983(19) -0.6319(2) -0.39852(15) 0.0205(5) Uani 1 1 d . . . . .
H11 H -0.557087 -0.691737 -0.352623 0.025 Uiso 1 1 calc R U . . .
C12 C -0.58372(18) -0.6661(2) -0.48478(15) 0.0197(4) Uani 1 1 d . . . . .
C13 C -0.72016(19) -0.6273(3) -0.40223(16) 0.0247(5) Uani 1 1 d . . . . .
H13 H -0.766088 -0.698913 -0.435976 0.030 Uiso 1 1 calc R U . . .
C14 C -0.7200(2) -0.6159(3) -0.30872(18) 0.0317(6) Uani 1 1 d . . . . .
H14A H -0.671841 -0.681467 -0.271822 0.038 Uiso 1 1 calc R U . . .
H14B H -0.792857 -0.627150 -0.305783 0.038 Uiso 1 1 calc R U . . .
C15 C -0.6773(3) -0.4724(3) -0.28287(19) 0.0365(7) Uani 1 1 d . . . . .
H15A H -0.729732 -0.420056 -0.265989 0.044 Uiso 1 1 calc R U . . .
H15B H -0.608458 -0.473455 -0.235724 0.044 Uiso 1 1 calc R U . . .
C16 C -0.6627(2) -0.4167(3) -0.36593(17) 0.0270(5) Uani 1 1 d . . . . .
H16 H -0.663238 -0.319238 -0.369745 0.032 Uiso 1 1 calc R U . . .
C17 C -0.7554(2) -0.4860(3) -0.43610(17) 0.0285(6) Uani 1 1 d . . . . .
H17A H -0.752119 -0.471401 -0.493578 0.034 Uiso 1 1 calc R U . . .
H17B H -0.826987 -0.462312 -0.434136 0.034 Uiso 1 1 calc R U . . .
C18 C -0.6390(2) -0.7792(2) -0.54127(16) 0.0237(5) Uani 1 1 d . . . . .
H18A H -0.663198 -0.764475 -0.603108 0.028 Uiso 1 1 calc R U . . .
H18B H -0.687726 -0.834070 -0.521705 0.028 Uiso 1 1 calc R U . . .
C19 C -0.5191(2) -0.7957(2) -0.49619(16) 0.0229(5) Uani 1 1 d . . . . .
C20 C -0.4752(2) -0.8778(2) -0.41486(17) 0.0256(5) Uani 1 1 d . . . . .
C21 C -0.4328(2) -0.8009(2) -0.53629(17) 0.0254(5) Uani 1 1 d . . . . .
C22 C -0.3429(2) -0.8653(2) -0.47805(18) 0.0274(5) Uani 1 1 d . . . . .
C23 C -0.2478(2) -0.8903(3) -0.4962(2) 0.0356(6) Uani 1 1 d . . . . .
H23 H -0.188150 -0.931282 -0.456106 0.043 Uiso 1 1 calc R U . . .
C24 C -0.2453(3) -0.8513(3) -0.5771(2) 0.0416(7) Uani 1 1 d . . . . .
H24 H -0.182491 -0.866114 -0.591200 0.050 Uiso 1 1 calc R U . . .
C25 C -0.3345(3) -0.7911(3) -0.6368(2) 0.0392(7) Uani 1 1 d . . . . .
H25 H -0.330821 -0.766593 -0.690376 0.047 Uiso 1 1 calc R U . . .
C26 C -0.4299(2) -0.7667(3) -0.61772(18) 0.0307(6) Uani 1 1 d . . . . .
H26 H -0.490270 -0.728319 -0.658537 0.037 Uiso 1 1 calc R U . . .
C27 C -0.2969(3) -0.9809(3) -0.3338(2) 0.0400(7) Uani 1 1 d . . . . .
H27A H -0.285220 -1.067298 -0.354281 0.060 Uiso 1 1 calc R U . . .
H27B H -0.330310 -0.990581 -0.290019 0.060 Uiso 1 1 calc R U . . .
H27C H -0.228195 -0.935900 -0.310144 0.060 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 C9 1.239(3) . ?
O2 C6 1.383(3) . ?
O2 C7 1.349(3) . ?
O3 C20 1.220(3) . ?
N1 C20 1.372(4) . ?
N1 C22 1.396(4) . ?
N1 C27 1.453(4) . ?
C1 C2 1.399(3) . ?
C1 C6 1.393(3) . ?
C1 C9 1.482(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.402(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C7 C8 1.354(3) . ?
C7 C12 1.472(3) . ?
C8 C9 1.431(3) . ?
C8 C10 1.506(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.565(3) . ?
C10 C16 1.545(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.538(3) . ?
C11 C13 1.544(3) . ?
C12 C18 1.491(3) . ?
C12 C19 1.592(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.539(3) . ?
C13 C17 1.537(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.551(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.543(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.531(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.496(4) . ?
C19 C20 1.511(3) . ?
C19 C21 1.477(4) . ?
C21 C22 1.399(4) . ?
C21 C26 1.393(4) . ?
C22 C23 1.385(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.396(4) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C6 116.73(18) . . ?
C20 N1 C22 111.3(2) . . ?
C20 N1 C27 123.1(3) . . ?
C22 N1 C27 124.8(2) . . ?
C2 C1 C9 120.9(2) . . ?
C6 C1 C2 118.3(2) . . ?
C6 C1 C9 120.9(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.7(2) . . ?
C6 C5 H5 120.7 . . ?
O2 C6 C1 121.9(2) . . ?
O2 C6 C5 116.2(2) . . ?
C5 C6 C1 122.0(2) . . ?
O2 C7 C8 125.8(2) . . ?
O2 C7 C12 120.3(2) . . ?
C8 C7 C12 113.9(2) . . ?
C7 C8 C9 121.0(2) . . ?
C7 C8 C10 110.5(2) . . ?
C9 C8 C10 128.5(2) . . ?
O1 C9 C1 121.5(2) . . ?
O1 C9 C8 125.0(2) . . ?
C8 C9 C1 113.4(2) . . ?
C8 C10 H10 112.0 . . ?
C8 C10 C11 104.20(18) . . ?
C8 C10 C16 113.3(2) . . ?
C11 C10 H10 112.0 . . ?
C16 C10 H10 112.0 . . ?
C16 C10 C11 102.78(19) . . ?
C10 C11 H11 110.9 . . ?
C12 C11 C10 106.28(18) . . ?
C12 C11 H11 110.9 . . ?
C12 C11 C13 114.47(19) . . ?
C13 C11 C10 102.96(19) . . ?
C13 C11 H11 110.9 . . ?
C7 C12 C11 104.31(19) . . ?
C7 C12 C18 124.8(2) . . ?
C7 C12 C19 118.4(2) . . ?
C11 C12 C19 121.90(19) . . ?
C18 C12 C11 124.0(2) . . ?
C18 C12 C19 57.96(15) . . ?
C11 C13 H13 114.8 . . ?
C14 C13 C11 107.2(2) . . ?
C14 C13 H13 114.8 . . ?
C17 C13 C11 102.59(19) . . ?
C17 C13 H13 114.8 . . ?
C17 C13 C14 101.2(2) . . ?
C13 C14 H14A 111.2 . . ?
C13 C14 H14B 111.2 . . ?
C13 C14 C15 103.0(2) . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 C14 103.4(2) . . ?
C16 C15 H15A 111.1 . . ?
C16 C15 H15B 111.1 . . ?
C10 C16 H16 114.7 . . ?
C15 C16 C10 108.2(2) . . ?
C15 C16 H16 114.7 . . ?
C17 C16 C10 101.2(2) . . ?
C17 C16 C15 101.8(2) . . ?
C17 C16 H16 114.7 . . ?
C13 C17 H17A 112.8 . . ?
C13 C17 H17B 112.8 . . ?
C16 C17 C13 94.6(2) . . ?
C16 C17 H17A 112.8 . . ?
C16 C17 H17B 112.8 . . ?
H17A C17 H17B 110.3 . . ?
C12 C18 H18A 117.3 . . ?
C12 C18 H18B 117.3 . . ?
C12 C18 C19 64.40(16) . . ?
H18A C18 H18B 114.4 . . ?
C19 C18 H18A 117.3 . . ?
C19 C18 H18B 117.3 . . ?
C18 C19 C12 57.65(15) . . ?
C18 C19 C20 121.6(2) . . ?
C20 C19 C12 113.6(2) . . ?
C21 C19 C12 126.1(2) . . ?
C21 C19 C18 127.0(2) . . ?
C21 C19 C20 104.8(2) . . ?
O3 C20 N1 126.2(2) . . ?
O3 C20 C19 127.7(2) . . ?
N1 C20 C19 106.1(2) . . ?
C22 C21 C19 107.2(2) . . ?
C26 C21 C19 133.2(2) . . ?
C26 C21 C22 119.3(2) . . ?
N1 C22 C21 109.6(2) . . ?
C23 C22 N1 127.8(3) . . ?
C23 C22 C21 122.6(3) . . ?
C22 C23 H23 121.4 . . ?
C22 C23 C24 117.2(3) . . ?
C24 C23 H23 121.4 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.3(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 C25 118.7(3) . . ?
C21 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 C9 -5.1(4) . . . . ?
O2 C7 C8 C10 176.8(2) . . . . ?
O2 C7 C12 C11 -172.75(19) . . . . ?
O2 C7 C12 C18 -21.1(3) . . . . ?
O2 C7 C12 C19 47.9(3) . . . . ?
N1 C22 C23 C24 174.8(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C2 C1 C6 O2 177.9(2) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C2 C1 C9 O1 2.0(3) . . . . ?
C2 C1 C9 C8 -176.1(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 O2 -177.5(2) . . . . ?
C4 C5 C6 C1 1.9(4) . . . . ?
C6 O2 C7 C8 6.8(3) . . . . ?
C6 O2 C7 C12 -171.7(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C9 O1 -179.6(2) . . . . ?
C6 C1 C9 C8 2.3(3) . . . . ?
C7 O2 C6 C1 -3.8(3) . . . . ?
C7 O2 C6 C5 175.6(2) . . . . ?
C7 C8 C9 O1 -177.7(2) . . . . ?
C7 C8 C9 C1 0.3(3) . . . . ?
C7 C8 C10 C11 -1.4(3) . . . . ?
C7 C8 C10 C16 -112.3(2) . . . . ?
C7 C12 C18 C19 104.4(3) . . . . ?
C7 C12 C19 C18 -115.3(2) . . . . ?
C7 C12 C19 C20 131.1(2) . . . . ?
C7 C12 C19 C21 -0.4(3) . . . . ?
C8 C7 C12 C11 8.6(3) . . . . ?
C8 C7 C12 C18 160.3(2) . . . . ?
C8 C7 C12 C19 -130.7(2) . . . . ?
C8 C10 C11 C12 6.4(2) . . . . ?
C8 C10 C11 C13 -114.3(2) . . . . ?
C8 C10 C16 C15 179.9(2) . . . . ?
C8 C10 C16 C17 73.4(2) . . . . ?
C9 C1 C2 C3 178.3(2) . . . . ?
C9 C1 C6 O2 -0.6(3) . . . . ?
C9 C1 C6 C5 -179.9(2) . . . . ?
C9 C8 C10 C11 -179.3(2) . . . . ?
C9 C8 C10 C16 69.8(3) . . . . ?
C10 C8 C9 O1 0.0(4) . . . . ?
C10 C8 C9 C1 178.0(2) . . . . ?
C10 C11 C12 C7 -8.8(2) . . . . ?
C10 C11 C12 C18 -160.8(2) . . . . ?
C10 C11 C12 C19 128.7(2) . . . . ?
C10 C11 C13 C14 -74.6(2) . . . . ?
C10 C11 C13 C17 31.5(2) . . . . ?
C10 C16 C17 C13 56.7(2) . . . . ?
C11 C10 C16 C15 68.1(2) . . . . ?
C11 C10 C16 C17 -38.4(2) . . . . ?
C11 C12 C18 C19 -109.3(2) . . . . ?
C11 C12 C19 C18 112.8(2) . . . . ?
C11 C12 C19 C20 -0.8(3) . . . . ?
C11 C12 C19 C21 -132.3(2) . . . . ?
C11 C13 C14 C15 70.2(3) . . . . ?
C11 C13 C17 C16 -54.3(2) . . . . ?
C12 C7 C8 C9 173.5(2) . . . . ?
C12 C7 C8 C10 -4.6(3) . . . . ?
C12 C11 C13 C14 170.5(2) . . . . ?
C12 C11 C13 C17 -83.4(2) . . . . ?
C12 C18 C19 C20 99.6(2) . . . . ?
C12 C18 C19 C21 -113.3(3) . . . . ?
C12 C19 C20 O3 46.6(3) . . . . ?
C12 C19 C20 N1 -131.4(2) . . . . ?
C12 C19 C21 C22 128.0(2) . . . . ?
C12 C19 C21 C26 -58.4(4) . . . . ?
C13 C11 C12 C7 104.2(2) . . . . ?
C13 C11 C12 C18 -47.8(3) . . . . ?
C13 C11 C12 C19 -118.3(2) . . . . ?
C13 C14 C15 C16 2.3(3) . . . . ?
C14 C13 C17 C16 56.3(2) . . . . ?
C14 C15 C16 C10 -72.8(3) . . . . ?
C14 C15 C16 C17 33.3(3) . . . . ?
C15 C16 C17 C13 -54.8(2) . . . . ?
C16 C10 C11 C12 124.77(19) . . . . ?
C16 C10 C11 C13 4.1(2) . . . . ?
C17 C13 C14 C15 -36.9(2) . . . . ?
C18 C12 C19 C20 -113.6(2) . . . . ?
C18 C12 C19 C21 114.9(3) . . . . ?
C18 C19 C20 O3 -18.7(4) . . . . ?
C18 C19 C20 N1 163.2(2) . . . . ?
C18 C19 C21 C22 -158.2(2) . . . . ?
C18 C19 C21 C26 15.4(4) . . . . ?
C19 C21 C22 N1 1.4(3) . . . . ?
C19 C21 C22 C23 178.3(2) . . . . ?
C19 C21 C26 C25 -176.6(3) . . . . ?
C20 N1 C22 C21 5.4(3) . . . . ?
C20 N1 C22 C23 -171.4(2) . . . . ?
C20 C19 C21 C22 -6.8(3) . . . . ?
C20 C19 C21 C26 166.8(3) . . . . ?
C21 C19 C20 O3 -172.1(2) . . . . ?
C21 C19 C20 N1 9.8(3) . . . . ?
C21 C22 C23 C24 -1.6(4) . . . . ?
C22 N1 C20 O3 172.4(2) . . . . ?
C22 N1 C20 C19 -9.5(3) . . . . ?
C22 C21 C26 C25 -3.6(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C26 0.4(5) . . . . ?
C24 C25 C26 C21 1.7(4) . . . . ?
C26 C21 C22 N1 -173.3(2) . . . . ?
C26 C21 C22 C23 3.7(4) . . . . ?
C27 N1 C20 O3 2.1(4) . . . . ?
C27 N1 C20 C19 -179.8(2) . . . . ?
C27 N1 C22 C21 175.5(2) . . . . ?
C27 N1 C22 C23 -1.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.208
_oxdiff_exptl_absorpt_empirical_full_min 0.517
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.0(3)
2 1.0(3)

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

data_115-4_2
_database_code_depnum_ccdc_archive 'CCDC 2058529'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 O2'
_chemical_formula_sum            'C23 H22 O2'
_chemical_formula_weight         330.40
_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                   12.0554(6)
_cell_length_b                   13.0086(9)
_cell_length_c                   13.4818(8)
_cell_angle_alpha                116.323(7)
_cell_angle_beta                 91.642(4)
_cell_angle_gamma                114.330(6)
_cell_volume                     1667.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4921
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      4.0080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11435
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.871
_diffrn_reflns_theta_min         3.787
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  78.00   1.00    1.00    --   40.73 -99.00  60.00   76
  2  ω     41.00  81.00   1.00    1.00    --  108.20-125.00  60.00   40
  3  ω     82.00 120.00   1.00    1.00    --  108.20-125.00  60.00   38
  4  ω     37.00 137.00   1.00    1.00    --  108.20 -61.00 120.00  100
  5  ω    118.00 152.00   1.00    1.00    --  108.20  45.00  90.00   34
  6  ω     92.00 178.00   1.00    1.00    --  108.20  77.00-120.00   86
  7  ω     94.00 168.00   1.00    1.00    --  108.20 125.00-180.00   74
  8  ω     38.00 156.00   1.00    1.00    --  108.20 -15.00  60.00  118
  9  ω     83.00 119.00   1.00    1.00    --  108.20-125.00-120.00   36
 10  ω     47.00 130.00   1.00    1.00    --  108.20 -77.00-120.00   83
 11  ω     32.00 129.00   1.00    1.00    --  108.20 -30.00-120.00   97
 12  ω     28.00  94.00   1.00    1.00    --  108.20 -95.00 120.00   66
 13  ω    -64.00  -2.00   1.00    1.00    --  -40.73 125.00 -90.00   62
 14  ω    -81.00 -53.00   1.00    1.00    --  -40.73 125.00-180.00   28
 15  ω    -39.00 -10.00   1.00    1.00    --  -40.73 125.00-180.00   29
 16  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00-180.00   99
 17  ω   -115.00 -29.00   1.00    1.00    --  -40.73 -38.00  90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0712566000
_diffrn_orient_matrix_UB_12      -0.0564635000
_diffrn_orient_matrix_UB_13      0.0382270000
_diffrn_orient_matrix_UB_21      -0.0153629000
_diffrn_orient_matrix_UB_22      0.0659948000
_diffrn_orient_matrix_UB_23      0.1220152000
_diffrn_orient_matrix_UB_31      -0.1255633000
_diffrn_orient_matrix_UB_32      -0.1223663000
_diffrn_orient_matrix_UB_33      -0.0327290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5215
_reflns_number_total             6532
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0860
_refine_ls_restrained_S_all      1.078
_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)+(0.1580P)²+0.6615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2346
_refine_ls_wR_factor_ref         0.2522
_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:
 C10(H10), C11(H11), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C21(H21), C24(H24), C27(H27), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34),
  C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B), C25(H25A,
 H25B), C26(H26A,H26B), C28(H28A,H28B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C43(H43), C44(H44), C45(H45), C46(H46)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B), C39(H39A,H39B)
;
_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 0.67893(16) 0.37503(19) 0.54283(16) 0.0335(4) Uani 1 1 d . . . . .
O2 O 1.04490(15) 0.56290(17) 0.73848(14) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.8927(2) 0.5412(2) 0.5990(2) 0.0239(5) Uani 1 1 d . . . . .
C2 C 0.8711(2) 0.5884(3) 0.5289(2) 0.0294(5) Uani 1 1 d . . . . .
H2 H 0.790355 0.550821 0.484023 0.035 Uiso 1 1 calc R U . . .
C3 C 0.9690(3) 0.6903(3) 0.5259(2) 0.0318(6) Uani 1 1 d . . . . .
H3 H 0.953684 0.721913 0.480181 0.038 Uiso 1 1 calc R U . . .
C4 C 1.0906(2) 0.7455(3) 0.5913(2) 0.0315(6) Uani 1 1 d . . . . .
H4 H 1.156339 0.812927 0.587865 0.038 Uiso 1 1 calc R U . . .
C5 C 1.1149(2) 0.7013(2) 0.6614(2) 0.0283(5) Uani 1 1 d . . . . .
H5 H 1.195992 0.738300 0.705264 0.034 Uiso 1 1 calc R U . . .
C6 C 1.0144(2) 0.5998(2) 0.6645(2) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.9474(2) 0.4645(2) 0.7432(2) 0.0254(5) Uani 1 1 d . . . . .
C8 C 0.8278(2) 0.3982(2) 0.6812(2) 0.0259(5) Uani 1 1 d . . . . .
C9 C 0.7875(2) 0.4301(2) 0.6011(2) 0.0243(5) Uani 1 1 d . . . . .
C10 C 0.7468(2) 0.2990(2) 0.7125(2) 0.0266(5) Uani 1 1 d . . . . .
H10 H 0.677207 0.314103 0.738808 0.032 Uiso 1 1 calc R U . . .
C11 C 0.8416(2) 0.3208(2) 0.8121(2) 0.0263(5) Uani 1 1 d . . . . .
H11 H 0.816275 0.347976 0.884019 0.032 Uiso 1 1 calc R U . . .
C12 C 0.9698(2) 0.4248(2) 0.8233(2) 0.0255(5) Uani 1 1 d . . . . .
C13 C 1.0808(2) 0.4688(3) 0.8910(2) 0.0296(5) Uani 1 1 d . . . . .
H13A H 1.153876 0.531387 0.889415 0.036 Uiso 1 1 calc R U . . .
H13B H 1.084959 0.436686 0.939628 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8337(2) 0.1867(2) 0.7661(2) 0.0277(5) Uani 1 1 d . . . . .
H14 H 0.906702 0.188592 0.802272 0.033 Uiso 1 1 calc R U . . .
C15 C 0.8184(2) 0.1408(3) 0.6374(2) 0.0326(6) Uani 1 1 d . . . . .
H15A H 0.888892 0.197947 0.622194 0.039 Uiso 1 1 calc R U . . .
H15B H 0.802775 0.051542 0.592355 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6999(2) 0.1557(3) 0.6225(2) 0.0302(6) Uani 1 1 d . . . . .
H16 H 0.666329 0.133330 0.544553 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6123(2) 0.0617(3) 0.6606(2) 0.0291(5) Uani 1 1 d . . . . .
H17 H 0.579038 -0.028110 0.597788 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7053(2) 0.0845(3) 0.7621(2) 0.0296(6) Uani 1 1 d . . . . .
H18 H 0.708709 0.003556 0.740589 0.035 Uiso 1 1 calc R U . . .
C19 C 0.6394(2) 0.1119(3) 0.8596(2) 0.0302(6) Uani 1 1 d . . . . .
H19 H 0.694737 0.158162 0.936574 0.036 Uiso 1 1 calc R U . . .
C20 C 0.5704(2) 0.1808(3) 0.8411(2) 0.0297(5) Uani 1 1 d . . . . .
H20A H 0.627576 0.265830 0.852028 0.036 Uiso 1 1 calc R U . . .
H20B H 0.511138 0.187468 0.887644 0.036 Uiso 1 1 calc R U . . .
C21 C 0.5051(2) 0.0771(3) 0.7139(2) 0.0297(6) Uani 1 1 d . . . . .
H21 H 0.452683 0.095713 0.674529 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4317(3) -0.0441(3) 0.7263(2) 0.0350(6) Uani 1 1 d . . . . .
H22A H 0.413910 -0.123436 0.656523 0.042 Uiso 1 1 calc R U . . .
H22B H 0.353125 -0.049410 0.744894 0.042 Uiso 1 1 calc R U . . .
C23 C 0.5247(3) -0.0199(3) 0.8276(3) 0.0347(6) Uani 1 1 d . . . . .
H23A H 0.487720 -0.014179 0.891548 0.042 Uiso 1 1 calc R U . . .
H23B H 0.548206 -0.088620 0.803137 0.042 Uiso 1 1 calc R U . . .
O3 O 0.14629(16) 0.16065(17) 0.23475(14) 0.0266(4) Uani 1 1 d . . . . .
O4 O 0.14164(18) 0.3352(2) 0.04334(18) 0.0381(5) Uani 1 1 d . . . . .
C24 C 0.6043(2) 0.6721(3) 0.2161(2) 0.0308(6) Uani 1 1 d . . . . .
H24 H 0.540359 0.679750 0.177589 0.037 Uiso 1 1 calc R U . . .
C25 C 0.7416(3) 0.7640(3) 0.2281(3) 0.0377(6) Uani 1 1 d . . . . .
H25A H 0.753142 0.849810 0.248311 0.045 Uiso 1 1 calc R U . . .
H25B H 0.766308 0.729158 0.157632 0.045 Uiso 1 1 calc R U . . .
C26 C 0.8183(2) 0.7687(3) 0.3272(3) 0.0355(6) Uani 1 1 d . . . . .
H26A H 0.876601 0.735060 0.300869 0.043 Uiso 1 1 calc R U . . .
H26B H 0.864885 0.856800 0.391424 0.043 Uiso 1 1 calc R U . . .
C27 C 0.7143(2) 0.6799(3) 0.3600(2) 0.0294(5) Uani 1 1 d . . . . .
H27 H 0.739210 0.694291 0.436809 0.035 Uiso 1 1 calc R U . . .
C28 C 0.6103(2) 0.7145(3) 0.3438(2) 0.0294(5) Uani 1 1 d . . . . .
H28A H 0.636466 0.806575 0.390887 0.035 Uiso 1 1 calc R U . . .
H28B H 0.532141 0.663019 0.355297 0.035 Uiso 1 1 calc R U . . .
C29 C 0.6667(2) 0.5396(2) 0.2627(2) 0.0270(5) Uani 1 1 d . . . . .
H29 H 0.739124 0.527634 0.240777 0.032 Uiso 1 1 calc R U . . .
C30 C 0.5902(2) 0.5343(3) 0.1618(2) 0.0297(6) Uani 1 1 d . . . . .
H30 H 0.631732 0.520365 0.099125 0.036 Uiso 1 1 calc R U . . .
C31 C 0.4619(2) 0.4115(3) 0.1228(2) 0.0288(5) Uani 1 1 d . . . . .
H31 H 0.413822 0.374532 0.044783 0.035 Uiso 1 1 calc R U . . .
C32 C 0.5069(2) 0.3230(3) 0.1379(2) 0.0314(6) Uani 1 1 d . . . . .
H32A H 0.437805 0.240871 0.122744 0.038 Uiso 1 1 calc R U . . .
H32B H 0.565604 0.307840 0.092936 0.038 Uiso 1 1 calc R U . . .
C33 C 0.5716(2) 0.4184(2) 0.2667(2) 0.0267(5) Uani 1 1 d . . . . .
H33 H 0.610953 0.386727 0.302970 0.032 Uiso 1 1 calc R U . . .
C34 C 0.4603(2) 0.4338(2) 0.3118(2) 0.0239(5) Uani 1 1 d . . . . .
H34 H 0.489465 0.515445 0.384369 0.029 Uiso 1 1 calc R U . . .
C35 C 0.3855(2) 0.4326(2) 0.2133(2) 0.0263(5) Uani 1 1 d . . . . .
H35 H 0.384128 0.515420 0.240359 0.032 Uiso 1 1 calc R U . . .
C36 C 0.2558(2) 0.3227(2) 0.1806(2) 0.0253(5) Uani 1 1 d . . . . .
C37 C 0.2499(2) 0.2634(2) 0.2417(2) 0.0241(5) Uani 1 1 d . . . . .
C38 C 0.3688(2) 0.3177(2) 0.3207(2) 0.0262(5) Uani 1 1 d . . . . .
C39 C 0.3925(3) 0.2724(3) 0.3856(2) 0.0303(6) Uani 1 1 d . . . . .
H39A H 0.329048 0.198769 0.382703 0.036 Uiso 1 1 calc R U . . .
H39B H 0.472403 0.314409 0.433869 0.036 Uiso 1 1 calc R U . . .
C40 C 0.1436(2) 0.2845(3) 0.1010(2) 0.0270(5) Uani 1 1 d . . . . .
C41 C 0.0288(2) 0.1778(2) 0.0985(2) 0.0259(5) Uani 1 1 d . . . . .
C42 C 0.0352(2) 0.1198(2) 0.1625(2) 0.0260(5) Uani 1 1 d . . . . .
C43 C -0.0705(2) 0.0164(3) 0.1579(2) 0.0298(5) Uani 1 1 d . . . . .
H43 H -0.063575 -0.022278 0.199860 0.036 Uiso 1 1 calc R U . . .
C44 C -0.1858(3) -0.0274(3) 0.0897(2) 0.0335(6) Uani 1 1 d . . . . .
H44 H -0.257357 -0.095948 0.085842 0.040 Uiso 1 1 calc R U . . .
C45 C -0.1955(2) 0.0307(3) 0.0267(2) 0.0334(6) Uani 1 1 d . . . . .
H45 H -0.273567 0.001288 -0.018186 0.040 Uiso 1 1 calc R U . . .
C46 C -0.0898(2) 0.1315(3) 0.0305(2) 0.0306(6) Uani 1 1 d . . . . .
H46 H -0.097225 0.169145 -0.012337 0.037 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 C9 1.230(3) . ?
O2 C6 1.382(3) . ?
O2 C7 1.364(3) . ?
C1 C2 1.404(3) . ?
C1 C6 1.386(3) . ?
C1 C9 1.492(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C7 C8 1.337(3) . ?
C7 C12 1.448(3) . ?
C8 C9 1.453(3) . ?
C8 C10 1.504(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.581(3) . ?
C10 C16 1.534(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.525(3) . ?
C11 C14 1.528(3) . ?
C12 C13 1.337(3) . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 H14 0.9800 . ?
C14 C15 1.541(4) . ?
C14 C18 1.550(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.538(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.549(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.580(3) . ?
C17 C21 1.537(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.537(4) . ?
C19 H19 0.9800 . ?
C19 C20 1.536(4) . ?
C19 C23 1.547(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.542(4) . ?
C21 H21 0.9800 . ?
C21 C22 1.545(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.569(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
O3 C37 1.364(3) . ?
O3 C42 1.380(3) . ?
O4 C40 1.227(3) . ?
C24 H24 0.9800 . ?
C24 C25 1.543(3) . ?
C24 C28 1.545(4) . ?
C24 C30 1.534(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.566(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.547(4) . ?
C27 H27 0.9800 . ?
C27 C28 1.536(3) . ?
C27 C29 1.534(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29 0.9800 . ?
C29 C30 1.581(3) . ?
C29 C33 1.546(3) . ?
C30 H30 0.9800 . ?
C30 C31 1.547(3) . ?
C31 H31 0.9800 . ?
C31 C32 1.542(4) . ?
C31 C35 1.545(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.542(3) . ?
C33 H33 0.9800 . ?
C33 C34 1.539(3) . ?
C34 H34 0.9800 . ?
C34 C35 1.574(3) . ?
C34 C38 1.518(3) . ?
C35 H35 0.9800 . ?
C35 C36 1.498(3) . ?
C36 C37 1.341(3) . ?
C36 C40 1.456(3) . ?
C37 C38 1.449(3) . ?
C38 C39 1.333(4) . ?
C39 H39A 0.9300 . ?
C39 H39B 0.9300 . ?
C40 C41 1.489(3) . ?
C41 C42 1.394(3) . ?
C41 C46 1.404(3) . ?
C42 C43 1.395(4) . ?
C43 H43 0.9300 . ?
C43 C44 1.383(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.392(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.381(4) . ?
C46 H46 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
C7 O2 C6 115.76(19) . . ?
C2 C1 C9 120.6(2) . . ?
C6 C1 C2 117.9(2) . . ?
C6 C1 C9 121.5(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
O2 C6 C1 122.5(2) . . ?
O2 C6 C5 115.1(2) . . ?
C1 C6 C5 122.4(2) . . ?
O2 C7 C12 119.3(2) . . ?
C8 C7 O2 126.8(2) . . ?
C8 C7 C12 113.9(2) . . ?
C7 C8 C9 121.1(2) . . ?
C7 C8 C10 111.4(2) . . ?
C9 C8 C10 127.4(2) . . ?
O1 C9 C1 122.9(2) . . ?
O1 C9 C8 124.7(2) . . ?
C8 C9 C1 112.3(2) . . ?
C8 C10 H10 111.3 . . ?
C8 C10 C11 103.27(19) . . ?
C8 C10 C16 116.4(2) . . ?
C11 C10 H10 111.3 . . ?
C16 C10 H10 111.3 . . ?
C16 C10 C11 102.8(2) . . ?
C10 C11 H11 111.6 . . ?
C12 C11 C10 105.49(19) . . ?
C12 C11 H11 111.6 . . ?
C12 C11 C14 113.3(2) . . ?
C14 C11 C10 102.8(2) . . ?
C14 C11 H11 111.6 . . ?
C7 C12 C11 105.8(2) . . ?
C13 C12 C7 126.8(2) . . ?
C13 C12 C11 127.3(2) . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C11 C14 H14 113.8 . . ?
C11 C14 C15 101.4(2) . . ?
C11 C14 C18 112.4(2) . . ?
C15 C14 H14 113.8 . . ?
C15 C14 C18 100.25(19) . . ?
C18 C14 H14 113.8 . . ?
C14 C15 H15A 112.8 . . ?
C14 C15 H15B 112.8 . . ?
H15A C15 H15B 110.3 . . ?
C16 C15 C14 94.4(2) . . ?
C16 C15 H15A 112.8 . . ?
C16 C15 H15B 112.8 . . ?
C10 C16 C15 101.6(2) . . ?
C10 C16 H16 114.0 . . ?
C10 C16 C17 112.2(2) . . ?
C15 C16 H16 114.0 . . ?
C15 C16 C17 99.6(2) . . ?
C17 C16 H16 114.0 . . ?
C16 C17 H17 109.0 . . ?
C16 C17 C18 103.0(2) . . ?
C18 C17 H17 109.0 . . ?
C21 C17 C16 123.4(2) . . ?
C21 C17 H17 109.0 . . ?
C21 C17 C18 102.60(19) . . ?
C14 C18 C17 102.35(19) . . ?
C14 C18 H18 109.0 . . ?
C17 C18 H18 109.0 . . ?
C19 C18 C14 123.6(2) . . ?
C19 C18 C17 103.0(2) . . ?
C19 C18 H18 109.0 . . ?
C18 C19 H19 114.8 . . ?
C18 C19 C23 106.4(2) . . ?
C20 C19 C18 105.0(2) . . ?
C20 C19 H19 114.8 . . ?
C20 C19 C23 99.6(2) . . ?
C23 C19 H19 114.8 . . ?
C19 C20 H20A 112.8 . . ?
C19 C20 H20B 112.8 . . ?
C19 C20 C21 94.5(2) . . ?
H20A C20 H20B 110.3 . . ?
C21 C20 H20A 112.8 . . ?
C21 C20 H20B 112.8 . . ?
C17 C21 C20 104.7(2) . . ?
C17 C21 H21 114.7 . . ?
C17 C21 C22 107.0(2) . . ?
C20 C21 H21 114.7 . . ?
C20 C21 C22 99.6(2) . . ?
C22 C21 H21 114.7 . . ?
C21 C22 H22A 111.2 . . ?
C21 C22 H22B 111.2 . . ?
C21 C22 C23 103.0(2) . . ?
H22A C22 H22B 109.1 . . ?
C23 C22 H22A 111.2 . . ?
C23 C22 H22B 111.2 . . ?
C19 C23 C22 102.9(2) . . ?
C19 C23 H23A 111.2 . . ?
C19 C23 H23B 111.2 . . ?
C22 C23 H23A 111.2 . . ?
C22 C23 H23B 111.2 . . ?
H23A C23 H23B 109.1 . . ?
C37 O3 C42 115.99(19) . . ?
C25 C24 H24 114.7 . . ?
C25 C24 C28 99.4(2) . . ?
C28 C24 H24 114.7 . . ?
C30 C24 H24 114.7 . . ?
C30 C24 C25 106.8(2) . . ?
C30 C24 C28 105.0(2) . . ?
C24 C25 H25A 111.2 . . ?
C24 C25 H25B 111.2 . . ?
C24 C25 C26 102.9(2) . . ?
H25A C25 H25B 109.1 . . ?
C26 C25 H25A 111.2 . . ?
C26 C25 H25B 111.2 . . ?
C25 C26 H26A 111.2 . . ?
C25 C26 H26B 111.2 . . ?
H26A C26 H26B 109.1 . . ?
C27 C26 C25 102.9(2) . . ?
C27 C26 H26A 111.2 . . ?
C27 C26 H26B 111.2 . . ?
C26 C27 H27 114.6 . . ?
C28 C27 C26 99.7(2) . . ?
C28 C27 H27 114.6 . . ?
C29 C27 C26 106.6(2) . . ?
C29 C27 H27 114.6 . . ?
C29 C27 C28 105.2(2) . . ?
C24 C28 H28A 112.9 . . ?
C24 C28 H28B 112.9 . . ?
C27 C28 C24 94.3(2) . . ?
C27 C28 H28A 112.9 . . ?
C27 C28 H28B 112.9 . . ?
H28A C28 H28B 110.3 . . ?
C27 C29 H29 109.0 . . ?
C27 C29 C30 102.7(2) . . ?
C27 C29 C33 123.6(2) . . ?
C30 C29 H29 109.0 . . ?
C33 C29 H29 109.0 . . ?
C33 C29 C30 102.60(19) . . ?
C24 C30 C29 102.8(2) . . ?
C24 C30 H30 109.1 . . ?
C24 C30 C31 122.8(2) . . ?
C29 C30 H30 109.1 . . ?
C31 C30 C29 102.89(19) . . ?
C31 C30 H30 109.1 . . ?
C30 C31 H31 114.1 . . ?
C32 C31 C30 99.9(2) . . ?
C32 C31 H31 114.1 . . ?
C32 C31 C35 101.6(2) . . ?
C35 C31 C30 111.7(2) . . ?
C35 C31 H31 114.1 . . ?
C31 C32 H32A 112.8 . . ?
C31 C32 H32B 112.8 . . ?
H32A C32 H32B 110.3 . . ?
C33 C32 C31 94.43(19) . . ?
C33 C32 H32A 112.8 . . ?
C33 C32 H32B 112.8 . . ?
C29 C33 H33 113.9 . . ?
C32 C33 C29 100.24(19) . . ?
C32 C33 H33 113.9 . . ?
C34 C33 C29 112.8(2) . . ?
C34 C33 C32 100.77(19) . . ?
C34 C33 H33 113.9 . . ?
C33 C34 H34 111.5 . . ?
C33 C34 C35 103.16(18) . . ?
C35 C34 H34 111.5 . . ?
C38 C34 C33 113.4(2) . . ?
C38 C34 H34 111.5 . . ?
C38 C34 C35 105.45(19) . . ?
C31 C35 C34 102.62(19) . . ?
C31 C35 H35 111.3 . . ?
C34 C35 H35 111.3 . . ?
C36 C35 C31 116.0(2) . . ?
C36 C35 C34 103.73(19) . . ?
C36 C35 H35 111.3 . . ?
C37 C36 C35 111.0(2) . . ?
C37 C36 C40 121.0(2) . . ?
C40 C36 C35 127.9(2) . . ?
O3 C37 C38 119.7(2) . . ?
C36 C37 O3 126.6(2) . . ?
C36 C37 C38 113.7(2) . . ?
C37 C38 C34 105.9(2) . . ?
C39 C38 C34 127.6(2) . . ?
C39 C38 C37 126.5(2) . . ?
C38 C39 H39A 120.0 . . ?
C38 C39 H39B 120.0 . . ?
H39A C39 H39B 120.0 . . ?
O4 C40 C36 124.6(2) . . ?
O4 C40 C41 122.9(2) . . ?
C36 C40 C41 112.5(2) . . ?
C42 C41 C40 121.4(2) . . ?
C42 C41 C46 117.7(2) . . ?
C46 C41 C40 120.9(2) . . ?
O3 C42 C41 122.4(2) . . ?
O3 C42 C43 115.4(2) . . ?
C41 C42 C43 122.2(2) . . ?
C42 C43 H43 120.7 . . ?
C44 C43 C42 118.6(2) . . ?
C44 C43 H43 120.7 . . ?
C43 C44 H44 119.8 . . ?
C43 C44 C45 120.4(2) . . ?
C45 C44 H44 119.8 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.4(2) . . ?
C46 C45 H45 119.8 . . ?
C41 C46 H46 119.7 . . ?
C45 C46 C41 120.6(2) . . ?
C45 C46 H46 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 C9 -2.3(4) . . . . ?
O2 C7 C8 C10 -178.6(2) . . . . ?
O2 C7 C12 C11 176.4(2) . . . . ?
O2 C7 C12 C13 -4.9(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C1 C6 O2 178.3(2) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C1 C9 O1 0.0(4) . . . . ?
C2 C1 C9 C8 -178.3(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 O2 -178.4(2) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C6 O2 C7 C8 2.5(4) . . . . ?
C6 O2 C7 C12 -176.5(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C1 C9 O1 -179.0(2) . . . . ?
C6 C1 C9 C8 2.6(3) . . . . ?
C7 O2 C6 C1 0.1(3) . . . . ?
C7 O2 C6 C5 179.5(2) . . . . ?
C7 C8 C9 O1 -178.7(2) . . . . ?
C7 C8 C9 C1 -0.4(3) . . . . ?
C7 C8 C10 C11 2.0(3) . . . . ?
C7 C8 C10 C16 -109.8(3) . . . . ?
C8 C7 C12 C11 -2.7(3) . . . . ?
C8 C7 C12 C13 175.9(2) . . . . ?
C8 C10 C11 C12 -3.4(2) . . . . ?
C8 C10 C11 C14 -122.4(2) . . . . ?
C8 C10 C16 C15 77.3(3) . . . . ?
C8 C10 C16 C17 -177.2(2) . . . . ?
C9 C1 C2 C3 -179.1(2) . . . . ?
C9 C1 C6 O2 -2.6(4) . . . . ?
C9 C1 C6 C5 178.1(2) . . . . ?
C9 C8 C10 C11 -174.1(2) . . . . ?
C9 C8 C10 C16 74.2(3) . . . . ?
C10 C8 C9 O1 -3.0(4) . . . . ?
C10 C8 C9 C1 175.4(2) . . . . ?
C10 C11 C12 C7 3.7(3) . . . . ?
C10 C11 C12 C13 -175.0(2) . . . . ?
C10 C11 C14 C15 36.3(2) . . . . ?
C10 C11 C14 C18 -69.9(2) . . . . ?
C10 C16 C17 C18 -69.4(2) . . . . ?
C10 C16 C17 C21 45.4(3) . . . . ?
C11 C10 C16 C15 -34.7(2) . . . . ?
C11 C10 C16 C17 70.8(2) . . . . ?
C11 C14 C15 C16 -56.8(2) . . . . ?
C11 C14 C18 C17 71.2(2) . . . . ?
C11 C14 C18 C19 -43.8(3) . . . . ?
C12 C7 C8 C9 176.8(2) . . . . ?
C12 C7 C8 C10 0.4(3) . . . . ?
C12 C11 C14 C15 -77.1(2) . . . . ?
C12 C11 C14 C18 176.71(19) . . . . ?
C14 C11 C12 C7 115.4(2) . . . . ?
C14 C11 C12 C13 -63.2(3) . . . . ?
C14 C15 C16 C10 56.1(2) . . . . ?
C14 C15 C16 C17 -59.1(2) . . . . ?
C14 C18 C19 C20 82.4(3) . . . . ?
C14 C18 C19 C23 -172.7(2) . . . . ?
C15 C14 C18 C17 -35.8(2) . . . . ?
C15 C14 C18 C19 -150.7(2) . . . . ?
C15 C16 C17 C18 37.5(2) . . . . ?
C15 C16 C17 C21 152.3(2) . . . . ?
C16 C10 C11 C12 118.0(2) . . . . ?
C16 C10 C11 C14 -1.0(2) . . . . ?
C16 C17 C18 C14 -1.0(2) . . . . ?
C16 C17 C18 C19 128.2(2) . . . . ?
C16 C17 C21 C20 -81.4(3) . . . . ?
C16 C17 C21 C22 173.5(2) . . . . ?
C17 C18 C19 C20 -32.2(3) . . . . ?
C17 C18 C19 C23 72.7(2) . . . . ?
C17 C21 C22 C23 72.4(3) . . . . ?
C18 C14 C15 C16 58.7(2) . . . . ?
C18 C17 C21 C20 33.6(2) . . . . ?
C18 C17 C21 C22 -71.5(2) . . . . ?
C18 C19 C20 C21 51.0(2) . . . . ?
C18 C19 C23 C22 -72.0(3) . . . . ?
C19 C20 C21 C17 -51.7(2) . . . . ?
C19 C20 C21 C22 58.8(2) . . . . ?
C20 C19 C23 C22 36.8(3) . . . . ?
C20 C21 C22 C23 -36.4(3) . . . . ?
C21 C17 C18 C14 -130.1(2) . . . . ?
C21 C17 C18 C19 -0.9(2) . . . . ?
C21 C22 C23 C19 -0.2(3) . . . . ?
C23 C19 C20 C21 -59.0(2) . . . . ?
O3 C37 C38 C34 -176.71(19) . . . . ?
O3 C37 C38 C39 4.6(4) . . . . ?
O3 C42 C43 C44 178.2(2) . . . . ?
O4 C40 C41 C42 178.0(2) . . . . ?
O4 C40 C41 C46 -1.4(4) . . . . ?
C24 C25 C26 C27 -0.7(3) . . . . ?
C24 C30 C31 C32 -151.5(2) . . . . ?
C24 C30 C31 C35 -44.7(3) . . . . ?
C25 C24 C28 C27 -59.3(2) . . . . ?
C25 C24 C30 C29 72.4(2) . . . . ?
C25 C24 C30 C31 -172.8(2) . . . . ?
C25 C26 C27 C28 -36.4(3) . . . . ?
C25 C26 C27 C29 72.7(3) . . . . ?
C26 C27 C28 C24 58.8(2) . . . . ?
C26 C27 C29 C30 -71.8(2) . . . . ?
C26 C27 C29 C33 173.5(2) . . . . ?
C27 C29 C30 C24 -0.4(2) . . . . ?
C27 C29 C30 C31 -128.8(2) . . . . ?
C27 C29 C33 C32 150.9(2) . . . . ?
C27 C29 C33 C34 44.6(3) . . . . ?
C28 C24 C25 C26 37.2(3) . . . . ?
C28 C24 C30 C29 -32.5(2) . . . . ?
C28 C24 C30 C31 82.3(3) . . . . ?
C28 C27 C29 C30 33.4(2) . . . . ?
C28 C27 C29 C33 -81.3(3) . . . . ?
C29 C27 C28 C24 -51.4(2) . . . . ?
C29 C30 C31 C32 -36.7(2) . . . . ?
C29 C30 C31 C35 70.1(2) . . . . ?
C29 C33 C34 C35 68.8(2) . . . . ?
C29 C33 C34 C38 -177.71(19) . . . . ?
C30 C24 C25 C26 -71.7(3) . . . . ?
C30 C24 C28 C27 51.0(2) . . . . ?
C30 C29 C33 C32 36.2(2) . . . . ?
C30 C29 C33 C34 -70.2(2) . . . . ?
C30 C31 C32 C33 58.6(2) . . . . ?
C30 C31 C35 C34 -71.7(2) . . . . ?
C30 C31 C35 C36 176.0(2) . . . . ?
C31 C32 C33 C29 -58.5(2) . . . . ?
C31 C32 C33 C34 57.2(2) . . . . ?
C31 C35 C36 C37 109.9(3) . . . . ?
C31 C35 C36 C40 -74.6(3) . . . . ?
C32 C31 C35 C34 34.0(2) . . . . ?
C32 C31 C35 C36 -78.4(2) . . . . ?
C32 C33 C34 C35 -37.3(2) . . . . ?
C32 C33 C34 C38 76.3(2) . . . . ?
C33 C29 C30 C24 128.8(2) . . . . ?
C33 C29 C30 C31 0.4(2) . . . . ?
C33 C34 C35 C31 2.0(2) . . . . ?
C33 C34 C35 C36 123.2(2) . . . . ?
C33 C34 C38 C37 -116.9(2) . . . . ?
C33 C34 C38 C39 61.9(3) . . . . ?
C34 C35 C36 C37 -1.8(3) . . . . ?
C34 C35 C36 C40 173.7(2) . . . . ?
C35 C31 C32 C33 -56.1(2) . . . . ?
C35 C34 C38 C37 -4.7(2) . . . . ?
C35 C34 C38 C39 174.0(2) . . . . ?
C35 C36 C37 O3 179.4(2) . . . . ?
C35 C36 C37 C38 -1.3(3) . . . . ?
C35 C36 C40 O4 4.1(4) . . . . ?
C35 C36 C40 C41 -174.6(2) . . . . ?
C36 C37 C38 C34 3.9(3) . . . . ?
C36 C37 C38 C39 -174.8(2) . . . . ?
C36 C40 C41 C42 -3.3(3) . . . . ?
C36 C40 C41 C46 177.3(2) . . . . ?
C37 O3 C42 C41 1.2(3) . . . . ?
C37 O3 C42 C43 -178.7(2) . . . . ?
C37 C36 C40 O4 179.1(3) . . . . ?
C37 C36 C40 C41 0.5(3) . . . . ?
C38 C34 C35 C31 -117.2(2) . . . . ?
C38 C34 C35 C36 4.0(2) . . . . ?
C40 C36 C37 O3 3.5(4) . . . . ?
C40 C36 C37 C38 -177.1(2) . . . . ?
C40 C41 C42 O3 2.6(4) . . . . ?
C40 C41 C42 C43 -177.5(2) . . . . ?
C40 C41 C46 C45 178.6(2) . . . . ?
C41 C42 C43 C44 -1.7(4) . . . . ?
C42 O3 C37 C36 -4.4(3) . . . . ?
C42 O3 C37 C38 176.3(2) . . . . ?
C42 C41 C46 C45 -0.8(4) . . . . ?
C42 C43 C44 C45 0.3(4) . . . . ?
C43 C44 C45 C46 0.8(4) . . . . ?
C44 C45 C46 C41 -0.5(4) . . . . ?
C46 C41 C42 O3 -177.9(2) . . . . ?
C46 C41 C42 C43 1.9(4) . . . . ?

_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 1.665
_oxdiff_exptl_absorpt_empirical_full_min 0.749
####################################################################### 
# 
# 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_189
_database_code_depnum_ccdc_archive 'CCDC 2058538'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2021-01-23
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O3'
_chemical_formula_sum            'C18 H18 O3'
_chemical_formula_weight         282.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   7.9260(13)
_cell_length_b                   8.5308(15)
_cell_length_c                   11.3433(18)
_cell_angle_alpha                74.736(15)
_cell_angle_beta                 89.146(13)
_cell_angle_gamma                64.955(16)
_cell_volume                     666.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1286
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.1130
_cell_measurement_theta_min      2.7690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.748
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  60.00   1.00    6.00    --  -11.27  57.00  60.00   98
  2  ω    -80.00  15.00   1.00    6.00    --  -11.27 -57.00 -90.00   95
  3  ω    -15.00  76.00   1.00    6.00    --   11.90  77.00-180.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0624594000
_diffrn_orient_matrix_UB_12      -0.0314234000
_diffrn_orient_matrix_UB_13      0.0540599000
_diffrn_orient_matrix_UB_21      0.0771896000
_diffrn_orient_matrix_UB_22      -0.0233297000
_diffrn_orient_matrix_UB_23      -0.0350299000
_diffrn_orient_matrix_UB_31      -0.0042602000
_diffrn_orient_matrix_UB_32      0.0873378000
_diffrn_orient_matrix_UB_33      -0.0101786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1672
_reflns_number_total             2349
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.055
_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)+(0.1427P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2078
_refine_ls_wR_factor_ref         0.2349
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.2212(3) 0.4920(3) 0.56028(19) 0.0298(6) Uani 1 1 d . . . . .
O2 O 0.3250(3) 0.9137(3) 0.35935(19) 0.0266(6) Uani 1 1 d . . . . .
O3 O 0.6032(3) 0.7351(3) 0.20450(19) 0.0293(6) Uani 1 1 d . . . . .
H3 H 0.656760 0.658387 0.269530 0.044 Uiso 1 1 calc R U . . .
C1 C 0.2268(4) 0.7736(4) 0.5452(3) 0.0227(8) Uani 1 1 d . . . . .
C2 C 0.1758(4) 0.7813(4) 0.6633(3) 0.0277(8) Uani 1 1 d . . . . .
H2 H 0.144765 0.692754 0.711408 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1709(5) 0.9154(4) 0.7092(3) 0.0298(8) Uani 1 1 d . . . . .
H3A H 0.136218 0.917969 0.787618 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2181(5) 1.0501(4) 0.6380(3) 0.0310(8) Uani 1 1 d . . . . .
H4 H 0.216953 1.140190 0.670144 0.037 Uiso 1 1 calc R U . . .
C5 C 0.2659(4) 1.0492(4) 0.5212(3) 0.0282(8) Uani 1 1 d . . . . .
H5 H 0.293985 1.139875 0.473153 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2718(4) 0.9109(4) 0.4758(3) 0.0241(8) Uani 1 1 d . . . . .
C7 C 0.3345(4) 0.7790(4) 0.3159(3) 0.0232(7) Uani 1 1 d . . . . .
C8 C 0.2932(4) 0.6411(4) 0.3742(3) 0.0223(7) Uani 1 1 d . . . . .
C9 C 0.2419(4) 0.6248(4) 0.4974(3) 0.0263(8) Uani 1 1 d . . . . .
C10 C 0.3240(4) 0.5142(4) 0.2991(3) 0.0225(7) Uani 1 1 d . . . . .
H10 H 0.418840 0.392718 0.341797 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3914(4) 0.5981(4) 0.1769(3) 0.0230(8) Uani 1 1 d . . . . .
H11 H 0.513554 0.509315 0.164827 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4108(4) 0.7668(4) 0.1931(3) 0.0238(8) Uani 1 1 d . . . . .
C13 C 0.3144(5) 0.9395(4) 0.0906(3) 0.0295(8) Uani 1 1 d . . . . .
H13A H 0.332957 1.034273 0.110322 0.044 Uiso 1 1 calc R U . . .
H13B H 0.182711 0.971753 0.080872 0.044 Uiso 1 1 calc R U . . .
H13C H 0.366191 0.922478 0.015408 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2425(5) 0.6288(4) 0.0779(3) 0.0276(8) Uani 1 1 d . . . . .
H14 H 0.233415 0.717101 -0.000089 0.033 Uiso 1 1 calc R U . . .
C15 C 0.0637(4) 0.6790(4) 0.1426(3) 0.0283(8) Uani 1 1 d . . . . .
H15A H 0.030050 0.788249 0.167098 0.034 Uiso 1 1 calc R U . . .
H15B H -0.041885 0.688137 0.094363 0.034 Uiso 1 1 calc R U . . .
C16 C 0.1445(4) 0.5090(4) 0.2507(3) 0.0267(8) Uani 1 1 d . . . . .
H16 H 0.058204 0.501541 0.312411 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2066(5) 0.3607(4) 0.1860(3) 0.0302(8) Uani 1 1 d . . . . .
H17A H 0.102963 0.335796 0.167245 0.036 Uiso 1 1 calc R U . . .
H17B H 0.307284 0.250201 0.235824 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2747(5) 0.4430(4) 0.0664(3) 0.0310(8) Uani 1 1 d . . . . .
H18A H 0.406213 0.369557 0.062532 0.037 Uiso 1 1 calc R U . . .
H18B H 0.202067 0.454777 -0.006102 0.037 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 C9 1.244(4) . ?
O2 C6 1.378(4) . ?
O2 C7 1.339(4) . ?
O3 H3 0.8200 . ?
O3 C12 1.433(4) . ?
C1 C2 1.404(4) . ?
C1 C6 1.407(5) . ?
C1 C9 1.466(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.407(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(5) . ?
C7 C8 1.356(4) . ?
C7 C12 1.521(4) . ?
C8 C9 1.438(4) . ?
C8 C10 1.487(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.580(4) . ?
C10 C16 1.555(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.567(4) . ?
C11 C14 1.531(5) . ?
C12 C13 1.509(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.533(5) . ?
C14 C18 1.536(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.523(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.528(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.557(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 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 O2 C6 117.2(2) . . ?
C12 O3 H3 109.5 . . ?
C2 C1 C6 117.1(3) . . ?
C2 C1 C9 121.9(3) . . ?
C6 C1 C9 120.9(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
O2 C6 C1 121.3(3) . . ?
O2 C6 C5 116.8(3) . . ?
C5 C6 C1 121.9(3) . . ?
O2 C7 C8 126.4(3) . . ?
O2 C7 C12 118.9(3) . . ?
C8 C7 C12 114.6(3) . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 C10 111.5(3) . . ?
C9 C8 C10 128.3(3) . . ?
O1 C9 C1 122.8(3) . . ?
O1 C9 C8 123.0(3) . . ?
C8 C9 C1 114.1(3) . . ?
C8 C10 H10 111.2 . . ?
C8 C10 C11 104.5(2) . . ?
C8 C10 C16 115.6(3) . . ?
C11 C10 H10 111.2 . . ?
C16 C10 H10 111.2 . . ?
C16 C10 C11 102.6(2) . . ?
C10 C11 H11 109.5 . . ?
C12 C11 C10 107.3(2) . . ?
C12 C11 H11 109.5 . . ?
C14 C11 C10 102.5(2) . . ?
C14 C11 H11 109.5 . . ?
C14 C11 C12 118.1(2) . . ?
O3 C12 C7 108.7(2) . . ?
O3 C12 C11 111.4(2) . . ?
O3 C12 C13 105.3(2) . . ?
C7 C12 C11 101.7(2) . . ?
C13 C12 C7 113.4(2) . . ?
C13 C12 C11 116.2(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14 114.6 . . ?
C11 C14 C15 102.9(3) . . ?
C11 C14 C18 107.5(2) . . ?
C15 C14 H14 114.6 . . ?
C15 C14 C18 101.1(3) . . ?
C18 C14 H14 114.6 . . ?
C14 C15 H15A 112.8 . . ?
C14 C15 H15B 112.8 . . ?
H15A C15 H15B 110.2 . . ?
C16 C15 C14 94.8(2) . . ?
C16 C15 H15A 112.8 . . ?
C16 C15 H15B 112.8 . . ?
C10 C16 H16 114.6 . . ?
C15 C16 C10 102.1(2) . . ?
C15 C16 H16 114.6 . . ?
C15 C16 C17 101.9(3) . . ?
C17 C16 C10 107.5(3) . . ?
C17 C16 H16 114.6 . . ?
C16 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C16 C17 C18 102.9(2) . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C14 C18 C17 103.3(3) . . ?
C14 C18 H18A 111.1 . . ?
C14 C18 H18B 111.1 . . ?
C17 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?

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
O2 C7 C8 C9 -3.3(5) . . . . ?
O2 C7 C8 C10 -178.7(3) . . . . ?
O2 C7 C12 O3 63.9(3) . . . . ?
O2 C7 C12 C11 -178.4(2) . . . . ?
O2 C7 C12 C13 -52.8(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C1 C6 O2 179.4(2) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C9 O1 -4.2(5) . . . . ?
C2 C1 C9 C8 179.2(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C4 C5 C6 -1.7(5) . . . . ?
C4 C5 C6 O2 -178.4(3) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C6 O2 C7 C8 1.4(4) . . . . ?
C6 O2 C7 C12 -174.1(2) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C6 C1 C9 O1 172.8(3) . . . . ?
C6 C1 C9 C8 -3.8(4) . . . . ?
C7 O2 C6 C1 -0.9(4) . . . . ?
C7 O2 C6 C5 178.7(3) . . . . ?
C7 C8 C9 O1 -172.4(3) . . . . ?
C7 C8 C9 C1 4.2(4) . . . . ?
C7 C8 C10 C11 -1.0(3) . . . . ?
C7 C8 C10 C16 -112.8(3) . . . . ?
C8 C7 C12 O3 -112.1(3) . . . . ?
C8 C7 C12 C11 5.5(3) . . . . ?
C8 C7 C12 C13 131.1(3) . . . . ?
C8 C10 C11 C12 4.3(3) . . . . ?
C8 C10 C11 C14 -120.8(3) . . . . ?
C8 C10 C16 C15 78.0(3) . . . . ?
C8 C10 C16 C17 -175.2(2) . . . . ?
C9 C1 C2 C3 176.8(3) . . . . ?
C9 C1 C6 O2 2.3(4) . . . . ?
C9 C1 C6 C5 -177.3(3) . . . . ?
C9 C8 C10 C11 -176.0(3) . . . . ?
C9 C8 C10 C16 72.2(4) . . . . ?
C10 C8 C9 O1 2.2(5) . . . . ?
C10 C8 C9 C1 178.8(3) . . . . ?
C10 C11 C12 O3 110.0(3) . . . . ?
C10 C11 C12 C7 -5.7(3) . . . . ?
C10 C11 C12 C13 -129.4(3) . . . . ?
C10 C11 C14 C15 34.5(3) . . . . ?
C10 C11 C14 C18 -71.7(3) . . . . ?
C10 C16 C17 C18 -71.5(3) . . . . ?
C11 C10 C16 C15 -34.9(3) . . . . ?
C11 C10 C16 C17 71.8(3) . . . . ?
C11 C14 C15 C16 -55.6(3) . . . . ?
C11 C14 C18 C17 72.7(3) . . . . ?
C12 C7 C8 C9 172.4(3) . . . . ?
C12 C7 C8 C10 -3.0(4) . . . . ?
C12 C11 C14 C15 -83.1(3) . . . . ?
C12 C11 C14 C18 170.6(2) . . . . ?
C14 C11 C12 O3 -134.9(3) . . . . ?
C14 C11 C12 C7 109.4(3) . . . . ?
C14 C11 C12 C13 -14.3(4) . . . . ?
C14 C15 C16 C10 55.0(3) . . . . ?
C14 C15 C16 C17 -56.1(3) . . . . ?
C15 C14 C18 C17 -34.8(3) . . . . ?
C15 C16 C17 C18 35.4(3) . . . . ?
C16 C10 C11 C12 125.2(2) . . . . ?
C16 C10 C11 C14 0.1(3) . . . . ?
C16 C17 C18 C14 -0.1(3) . . . . ?
C18 C14 C15 C16 55.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.138
_oxdiff_exptl_absorpt_empirical_full_min 0.628
####################################################################### 
# 
# 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_115-11
_database_code_depnum_ccdc_archive 'CCDC 2058531'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-11-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 O2'
_chemical_formula_sum            'C32 H22 O2'
_chemical_formula_weight         438.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.7006(6)
_cell_length_b                   5.4053(2)
_cell_length_c                   28.9327(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2142.64(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7630
_cell_measurement_theta_min      3.0330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            5047
_diffrn_reflns_point_group_measured_fraction_full 0.657
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.863
_diffrn_reflns_theta_min         3.055
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     53.00  89.00   1.00    1.00    --   40.73  38.00  30.00   36
  2  ω    136.00 162.00   1.00    2.02    --  107.58 125.00 120.00   26
  3  ω     96.00 173.00   1.00    2.02    --  107.58 125.00 -30.00   77
  4  ω    149.00 175.00   1.00    2.02    --  107.58 125.00-120.00   26
  5  ω    128.00 174.00   1.00    2.02    --  107.58  45.00-150.00   46
  6  ω     96.00 123.00   1.00    2.02    --  107.58 125.00-120.00   27
  7  ω    -56.00 -18.00   1.00    1.00    --  -40.73  77.00  30.00   38
  8  ω    -64.00  33.00   1.00    1.00    --  -40.73  38.00-180.00   97
  9  ω     38.00 118.00   1.00    2.02    --  107.58-125.00 -30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0276157000
_diffrn_orient_matrix_UB_12      -0.1082708000
_diffrn_orient_matrix_UB_13      0.0134275000
_diffrn_orient_matrix_UB_21      0.2836074000
_diffrn_orient_matrix_UB_22      -0.0100138000
_diffrn_orient_matrix_UB_23      0.0022168000
_diffrn_orient_matrix_UB_31      -0.0051918000
_diffrn_orient_matrix_UB_32      0.0286363000
_diffrn_orient_matrix_UB_33      0.0514825000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.283
_reflns_Friedel_fraction_full    0.302
_reflns_Friedel_fraction_max     0.287
_reflns_number_gt                2668
_reflns_number_total             2774
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.6(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.080
_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)+(0.0434P)²+0.4827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -0.6(5)
 1.6(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C24(H24), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.79675(16) -0.9622(5) -0.62656(8) 0.0387(5) Uani 1 1 d . . . . .
O2 O -0.52570(14) -0.6277(4) -0.63413(8) 0.0280(4) Uani 1 1 d . . . . .
C1 C -0.6393(2) -0.9392(6) -0.66163(9) 0.0267(6) Uani 1 1 d . . . . .
C2 C -0.6546(2) -1.1439(6) -0.69082(10) 0.0316(7) Uani 1 1 d . . . . .
H2 H -0.714689 -1.223882 -0.690821 0.038 Uiso 1 1 calc R U . . .
C3 C -0.5808(2) -1.2267(6) -0.71949(10) 0.0348(7) Uani 1 1 d . . . . .
H3 H -0.591028 -1.362766 -0.738552 0.042 Uiso 1 1 calc R U . . .
C4 C -0.4911(2) -1.1053(7) -0.71970(11) 0.0371(7) Uani 1 1 d . . . . .
H4 H -0.441776 -1.160776 -0.739219 0.044 Uiso 1 1 calc R U . . .
C5 C -0.4741(2) -0.9047(7) -0.69149(10) 0.0340(7) Uani 1 1 d . . . . .
H5 H -0.414087 -0.824440 -0.691827 0.041 Uiso 1 1 calc R U . . .
C6 C -0.5485(2) -0.8247(5) -0.66252(9) 0.0270(6) Uani 1 1 d . . . . .
C7 C -0.5965(2) -0.5544(5) -0.60442(9) 0.0245(5) Uani 1 1 d . . . . .
C8 C -0.6867(2) -0.6516(5) -0.60058(9) 0.0239(6) Uani 1 1 d . . . . .
C9 C -0.7163(2) -0.8585(5) -0.62912(9) 0.0263(6) Uani 1 1 d . . . . .
C10 C -0.74367(19) -0.5255(5) -0.56284(9) 0.0228(5) Uani 1 1 d . . . . .
H10 H -0.802439 -0.444026 -0.574720 0.027 Uiso 1 1 calc R U . . .
C11 C -0.66848(19) -0.3345(5) -0.54241(9) 0.0225(6) Uani 1 1 d . . . . .
H11 H -0.695260 -0.166471 -0.543095 0.027 Uiso 1 1 calc R U . . .
C12 C -0.5782(2) -0.3526(5) -0.57211(9) 0.0238(6) Uani 1 1 d . . . . .
C13 C -0.6553(2) -0.4254(5) -0.49183(9) 0.0224(5) Uani 1 1 d . . . . .
H13 H -0.594836 -0.371476 -0.476781 0.027 Uiso 1 1 calc R U . . .
C14 C -0.66603(19) -0.7071(5) -0.49754(9) 0.0220(5) Uani 1 1 d . . . . .
H14A H -0.616185 -0.777659 -0.517362 0.026 Uiso 1 1 calc R U . . .
H14B H -0.667679 -0.793618 -0.468179 0.026 Uiso 1 1 calc R U . . .
C15 C -0.76645(18) -0.6957(5) -0.52098(9) 0.0203(5) Uani 1 1 d . . . . .
H15 H -0.794472 -0.856872 -0.529021 0.024 Uiso 1 1 calc R U . . .
C16 C -0.8276(2) -0.5415(5) -0.48728(9) 0.0221(5) Uani 1 1 d . . . . .
H16 H -0.886554 -0.465925 -0.500235 0.027 Uiso 1 1 calc R U . . .
C17 C -0.7494(2) -0.3541(5) -0.46639(10) 0.0232(5) Uani 1 1 d . . . . .
H17 H -0.767222 -0.178741 -0.468134 0.028 Uiso 1 1 calc R U . . .
C18 C -0.7699(2) -0.4788(5) -0.42029(10) 0.0240(6) Uani 1 1 d . . . . .
C19 C -0.8366(2) -0.6382(5) -0.43779(9) 0.0230(6) Uani 1 1 d . . . . .
C20 C -0.88473(19) -0.8235(5) -0.41097(9) 0.0228(5) Uani 1 1 d . . . . .
C21 C -0.8587(2) -0.8294(5) -0.36340(10) 0.0243(6) Uani 1 1 d . . . . .
C22 C -0.7874(2) -0.6554(5) -0.34400(9) 0.0254(6) Uani 1 1 d . . . . .
C23 C -0.7409(2) -0.4780(5) -0.37291(10) 0.0256(6) Uani 1 1 d . . . . .
C24 C -0.6717(2) -0.3119(6) -0.35480(10) 0.0314(7) Uani 1 1 d . . . . .
H24 H -0.641097 -0.198229 -0.374109 0.038 Uiso 1 1 calc R U . . .
C25 C -0.6494(2) -0.3180(6) -0.30857(11) 0.0355(7) Uani 1 1 d . . . . .
H25 H -0.604098 -0.207325 -0.296520 0.043 Uiso 1 1 calc R U . . .
C26 C -0.6945(2) -0.4894(6) -0.27960(10) 0.0348(7) Uani 1 1 d . . . . .
H26 H -0.679256 -0.491806 -0.248282 0.042 Uiso 1 1 calc R U . . .
C27 C -0.7613(2) -0.6547(6) -0.29690(11) 0.0315(7) Uani 1 1 d . . . . .
H27 H -0.789969 -0.768845 -0.277052 0.038 Uiso 1 1 calc R U . . .
C28 C -0.9040(2) -1.0123(6) -0.33582(10) 0.0291(6) Uani 1 1 d . . . . .
H28 H -0.888863 -1.020705 -0.304517 0.035 Uiso 1 1 calc R U . . .
C29 C -0.9697(2) -1.1784(6) -0.35402(11) 0.0328(7) Uani 1 1 d . . . . .
H29 H -0.998329 -1.296624 -0.334988 0.039 Uiso 1 1 calc R U . . .
C30 C -0.9936(2) -1.1704(5) -0.40060(11) 0.0295(6) Uani 1 1 d . . . . .
H30 H -1.037604 -1.284120 -0.412775 0.035 Uiso 1 1 calc R U . . .
C31 C -0.9524(2) -0.9948(5) -0.42870(10) 0.0252(6) Uani 1 1 d . . . . .
H31 H -0.969362 -0.988808 -0.459809 0.030 Uiso 1 1 calc R U . . .
C32 C -0.4983(2) -0.2112(6) -0.57114(11) 0.0297(6) Uani 1 1 d . . . . .
H32A H -0.491(2) -0.074(6) -0.5500(12) 0.031(9) Uiso 1 1 d . . . . .
H32B H -0.439(3) -0.239(7) -0.5925(13) 0.048(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.239(3) . ?
O2 C6 1.381(3) . ?
O2 C7 1.355(3) . ?
C1 C2 1.408(4) . ?
C1 C6 1.390(4) . ?
C1 C9 1.479(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(4) . ?
C7 C8 1.348(4) . ?
C7 C12 1.458(4) . ?
C8 C9 1.448(4) . ?
C8 C10 1.505(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.574(4) . ?
C10 C15 1.552(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.510(4) . ?
C11 C13 1.554(4) . ?
C12 C32 1.335(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.539(4) . ?
C13 C17 1.534(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.535(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.532(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.594(4) . ?
C16 C19 1.529(4) . ?
C17 H17 0.9800 . ?
C17 C18 1.521(4) . ?
C18 C19 1.354(4) . ?
C18 C23 1.427(4) . ?
C19 C20 1.428(4) . ?
C20 C21 1.422(4) . ?
C20 C31 1.407(4) . ?
C21 C22 1.468(4) . ?
C21 C28 1.414(4) . ?
C22 C23 1.423(4) . ?
C22 C27 1.409(4) . ?
C23 C24 1.407(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.372(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.394(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.377(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.388(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.372(4) . ?
C31 H31 0.9300 . ?
C32 H32A 0.97(4) . ?
C32 H32B 1.03(4) . ?

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 O2 C6 116.2(2) . . ?
C2 C1 C9 120.5(3) . . ?
C6 C1 C2 118.2(3) . . ?
C6 C1 C9 121.3(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
O2 C6 C1 122.3(2) . . ?
O2 C6 C5 115.7(3) . . ?
C5 C6 C1 122.0(3) . . ?
O2 C7 C12 120.2(2) . . ?
C8 C7 O2 126.5(3) . . ?
C8 C7 C12 113.4(2) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 C10 111.0(2) . . ?
C9 C8 C10 128.2(2) . . ?
O1 C9 C1 122.6(3) . . ?
O1 C9 C8 124.3(3) . . ?
C8 C9 C1 113.0(2) . . ?
C8 C10 H10 112.0 . . ?
C8 C10 C11 103.3(2) . . ?
C8 C10 C15 113.7(2) . . ?
C11 C10 H10 112.0 . . ?
C15 C10 H10 112.0 . . ?
C15 C10 C11 103.1(2) . . ?
C10 C11 H11 110.8 . . ?
C12 C11 C10 106.3(2) . . ?
C12 C11 H11 110.8 . . ?
C12 C11 C13 114.9(2) . . ?
C13 C11 C10 102.9(2) . . ?
C13 C11 H11 110.8 . . ?
C7 C12 C11 105.8(2) . . ?
C32 C12 C7 125.6(3) . . ?
C32 C12 C11 128.5(3) . . ?
C11 C13 H13 115.0 . . ?
C14 C13 C11 101.6(2) . . ?
C14 C13 H13 115.0 . . ?
C17 C13 C11 106.0(2) . . ?
C17 C13 H13 115.0 . . ?
C17 C13 C14 102.7(2) . . ?
C13 C14 H14A 112.7 . . ?
C13 C14 H14B 112.7 . . ?
H14A C14 H14B 110.2 . . ?
C15 C14 C13 95.4(2) . . ?
C15 C14 H14A 112.7 . . ?
C15 C14 H14B 112.7 . . ?
C10 C15 H15 114.9 . . ?
C14 C15 C10 100.9(2) . . ?
C14 C15 H15 114.9 . . ?
C16 C15 C10 106.5(2) . . ?
C16 C15 C14 103.3(2) . . ?
C16 C15 H15 114.9 . . ?
C15 C16 H16 115.7 . . ?
C15 C16 C17 102.7(2) . . ?
C17 C16 H16 115.7 . . ?
C19 C16 C15 117.0(2) . . ?
C19 C16 H16 115.7 . . ?
C19 C16 C17 85.2(2) . . ?
C13 C17 C16 102.9(2) . . ?
C13 C17 H17 115.3 . . ?
C16 C17 H17 115.3 . . ?
C18 C17 C13 117.7(2) . . ?
C18 C17 C16 85.78(19) . . ?
C18 C17 H17 115.3 . . ?
C19 C18 C17 94.5(2) . . ?
C19 C18 C23 123.3(3) . . ?
C23 C18 C17 142.1(3) . . ?
C18 C19 C16 94.5(2) . . ?
C18 C19 C20 123.7(3) . . ?
C20 C19 C16 141.8(3) . . ?
C21 C20 C19 115.2(2) . . ?
C31 C20 C19 124.6(3) . . ?
C31 C20 C21 120.2(2) . . ?
C20 C21 C22 121.5(2) . . ?
C28 C21 C20 116.9(3) . . ?
C28 C21 C22 121.6(3) . . ?
C23 C22 C21 120.3(2) . . ?
C27 C22 C21 122.7(3) . . ?
C27 C22 C23 116.9(3) . . ?
C22 C23 C18 116.0(3) . . ?
C24 C23 C18 123.2(3) . . ?
C24 C23 C22 120.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.6(3) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 H27 119.2 . . ?
C26 C27 C22 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C21 C28 H28 119.1 . . ?
C29 C28 C21 121.8(3) . . ?
C29 C28 H28 119.1 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0(3) . . ?
C31 C30 H30 120.0 . . ?
C20 C31 H31 119.6 . . ?
C30 C31 C20 120.7(3) . . ?
C30 C31 H31 119.6 . . ?
C12 C32 H32A 123(2) . . ?
C12 C32 H32B 123(2) . . ?
H32A C32 H32B 114(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 C9 1.4(4) . . . . ?
O2 C7 C8 C10 178.5(3) . . . . ?
O2 C7 C12 C11 -175.8(2) . . . . ?
O2 C7 C12 C32 6.3(4) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C1 C6 O2 -178.0(3) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C9 O1 -1.2(4) . . . . ?
C2 C1 C9 C8 177.7(2) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 O2 178.1(3) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C6 O2 C7 C8 -1.3(4) . . . . ?
C6 O2 C7 C12 178.2(2) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C6 C1 C9 O1 -177.7(3) . . . . ?
C6 C1 C9 C8 1.3(4) . . . . ?
C7 O2 C6 C1 1.3(4) . . . . ?
C7 O2 C6 C5 -177.5(3) . . . . ?
C7 C8 C9 O1 177.7(3) . . . . ?
C7 C8 C9 C1 -1.2(4) . . . . ?
C7 C8 C10 C11 -2.1(3) . . . . ?
C7 C8 C10 C15 -113.1(3) . . . . ?
C8 C7 C12 C11 3.8(3) . . . . ?
C8 C7 C12 C32 -174.1(3) . . . . ?
C8 C10 C11 C12 4.2(3) . . . . ?
C8 C10 C11 C13 -116.9(2) . . . . ?
C8 C10 C15 C14 74.7(3) . . . . ?
C8 C10 C15 C16 -177.8(2) . . . . ?
C9 C1 C2 C3 -176.7(3) . . . . ?
C9 C1 C6 O2 -1.4(4) . . . . ?
C9 C1 C6 C5 177.3(3) . . . . ?
C9 C8 C10 C11 174.8(3) . . . . ?
C9 C8 C10 C15 63.8(4) . . . . ?
C10 C8 C9 O1 1.1(5) . . . . ?
C10 C8 C9 C1 -177.8(3) . . . . ?
C10 C11 C12 C7 -4.8(3) . . . . ?
C10 C11 C12 C32 173.0(3) . . . . ?
C10 C11 C13 C14 33.5(2) . . . . ?
C10 C11 C13 C17 -73.5(2) . . . . ?
C10 C15 C16 C17 -72.7(2) . . . . ?
C10 C15 C16 C19 -163.7(2) . . . . ?
C11 C10 C15 C14 -36.5(2) . . . . ?
C11 C10 C15 C16 71.1(2) . . . . ?
C11 C13 C14 C15 -55.6(2) . . . . ?
C11 C13 C17 C16 71.6(2) . . . . ?
C11 C13 C17 C18 163.6(2) . . . . ?
C12 C7 C8 C9 -178.2(2) . . . . ?
C12 C7 C8 C10 -1.0(3) . . . . ?
C12 C11 C13 C14 -81.5(3) . . . . ?
C12 C11 C13 C17 171.5(2) . . . . ?
C13 C11 C12 C7 108.2(2) . . . . ?
C13 C11 C12 C32 -74.0(4) . . . . ?
C13 C14 C15 C10 56.5(2) . . . . ?
C13 C14 C15 C16 -53.5(2) . . . . ?
C13 C17 C18 C19 -102.5(3) . . . . ?
C13 C17 C18 C23 75.1(5) . . . . ?
C14 C13 C17 C16 -34.5(3) . . . . ?
C14 C13 C17 C18 57.5(3) . . . . ?
C14 C15 C16 C17 33.1(2) . . . . ?
C14 C15 C16 C19 -58.0(3) . . . . ?
C15 C10 C11 C12 122.8(2) . . . . ?
C15 C10 C11 C13 1.8(2) . . . . ?
C15 C16 C17 C13 1.0(3) . . . . ?
C15 C16 C17 C18 -116.5(2) . . . . ?
C15 C16 C19 C18 101.7(3) . . . . ?
C15 C16 C19 C20 -75.3(4) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C16 C17 C18 C23 177.5(4) . . . . ?
C16 C19 C20 C21 177.0(3) . . . . ?
C16 C19 C20 C31 -2.0(5) . . . . ?
C17 C13 C14 C15 53.9(2) . . . . ?
C17 C16 C19 C18 -0.1(2) . . . . ?
C17 C16 C19 C20 -177.1(4) . . . . ?
C17 C18 C19 C16 0.1(2) . . . . ?
C17 C18 C19 C20 177.9(2) . . . . ?
C17 C18 C23 C22 -177.9(3) . . . . ?
C17 C18 C23 C24 3.0(6) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C18 C19 C20 C31 -178.4(3) . . . . ?
C18 C23 C24 C25 178.2(3) . . . . ?
C19 C16 C17 C13 117.6(2) . . . . ?
C19 C16 C17 C18 0.11(19) . . . . ?
C19 C18 C23 C22 -0.8(4) . . . . ?
C19 C18 C23 C24 -179.9(3) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C19 C20 C21 C28 -179.2(2) . . . . ?
C19 C20 C31 C30 178.5(3) . . . . ?
C20 C21 C22 C23 -1.2(4) . . . . ?
C20 C21 C22 C27 179.0(3) . . . . ?
C20 C21 C28 C29 0.4(4) . . . . ?
C21 C20 C31 C30 -0.4(4) . . . . ?
C21 C22 C23 C18 1.5(4) . . . . ?
C21 C22 C23 C24 -179.4(3) . . . . ?
C21 C22 C27 C26 -179.8(3) . . . . ?
C21 C28 C29 C30 0.0(5) . . . . ?
C22 C21 C28 C29 -179.0(3) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C18 C19 C16 -178.1(3) . . . . ?
C23 C18 C19 C20 -0.3(4) . . . . ?
C23 C22 C27 C26 0.4(4) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C24 C25 C26 C27 0.3(5) . . . . ?
C25 C26 C27 C22 -0.8(5) . . . . ?
C27 C22 C23 C18 -178.8(3) . . . . ?
C27 C22 C23 C24 0.4(4) . . . . ?
C28 C21 C22 C23 178.1(3) . . . . ?
C28 C21 C22 C27 -1.6(4) . . . . ?
C28 C29 C30 C31 -0.7(5) . . . . ?
C29 C30 C31 C20 0.9(4) . . . . ?
C31 C20 C21 C22 179.2(2) . . . . ?
C31 C20 C21 C28 -0.2(4) . . . . ?

_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.486
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -0.6(5)
2 1.6(5)

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

data_zw178
_database_code_depnum_ccdc_archive 'CCDC 2058536'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 F3 O2'
_chemical_formula_sum            'C20 H17 F3 O2'
_chemical_formula_weight         346.33
_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'
F F 0.0171 0.0103 '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                   9.7519(7)
_cell_length_b                   15.4163(10)
_cell_length_c                   10.9175(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.715(8)
_cell_angle_gamma                90
_cell_volume                     1580.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3305
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.8500
_cell_measurement_theta_min      2.5450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7021
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.169
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  62.00   1.00    1.00    --   12.05 178.00   0.00   26
  2  ω     -8.00  85.00   1.00    1.00    --   12.05  57.00 120.00   93
  3  ω    -57.00  23.00   1.00    1.00    --   12.05 -37.00 -30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0434083000
_diffrn_orient_matrix_UB_12      -0.0117019000
_diffrn_orient_matrix_UB_13      0.0401475000
_diffrn_orient_matrix_UB_21      0.0569156000
_diffrn_orient_matrix_UB_22      0.0097814000
_diffrn_orient_matrix_UB_23      0.0541541000
_diffrn_orient_matrix_UB_31      -0.0245076000
_diffrn_orient_matrix_UB_32      0.0433654000
_diffrn_orient_matrix_UB_33      -0.0013372000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2375
_reflns_number_total             2790
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.050
_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)+(0.0342P)²+0.6067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0895
_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:
 C10(H10), C11(H11), C13(H13), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_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
F1 F -0.89346(11) -0.47654(7) -0.85750(11) 0.0420(3) Uani 1 1 d . . . . .
F2 F -0.84256(11) -0.56605(7) -0.70153(10) 0.0346(3) Uani 1 1 d . . . . .
F3 F -0.86993(11) -0.61181(6) -0.89155(10) 0.0353(3) Uani 1 1 d . . . . .
O1 O -0.58212(14) -0.16585(7) -0.61664(12) 0.0315(3) Uani 1 1 d . . . . .
O2 O -0.71465(11) -0.41743(7) -0.59246(10) 0.0204(3) Uani 1 1 d . . . . .
C1 C -0.72922(17) -0.26478(10) -0.54258(15) 0.0196(4) Uani 1 1 d . . . . .
C2 C -0.79348(18) -0.20253(11) -0.48270(16) 0.0235(4) Uani 1 1 d . . . . .
H2 H -0.772240 -0.144179 -0.489096 0.028 Uiso 1 1 calc R U . . .
C3 C -0.88716(18) -0.22607(11) -0.41480(17) 0.0266(4) Uani 1 1 d . . . . .
H3 H -0.928885 -0.183767 -0.375891 0.032 Uiso 1 1 calc R U . . .
C4 C -0.91982(18) -0.31303(11) -0.40408(16) 0.0260(4) Uani 1 1 d . . . . .
H4 H -0.981754 -0.328820 -0.356425 0.031 Uiso 1 1 calc R U . . .
C5 C -0.86084(18) -0.37590(10) -0.46371(16) 0.0231(4) Uani 1 1 d . . . . .
H5 H -0.883248 -0.434087 -0.457513 0.028 Uiso 1 1 calc R U . . .
C6 C -0.76763(17) -0.35110(10) -0.53307(14) 0.0184(3) Uani 1 1 d . . . . .
C7 C -0.62340(17) -0.39443(10) -0.66034(14) 0.0185(4) Uani 1 1 d . . . . .
C8 C -0.57202(17) -0.31447(10) -0.66880(14) 0.0192(4) Uani 1 1 d . . . . .
C9 C -0.62248(18) -0.24123(10) -0.61092(15) 0.0216(4) Uani 1 1 d . . . . .
C10 C -0.46779(18) -0.31477(10) -0.74765(15) 0.0216(4) Uani 1 1 d . . . . .
H10 H -0.495908 -0.273787 -0.818669 0.026 Uiso 1 1 calc R U . . .
C11 C -0.46998(17) -0.41104(10) -0.79647(15) 0.0216(4) Uani 1 1 d . . . . .
H11 H -0.505324 -0.413594 -0.889409 0.026 Uiso 1 1 calc R U . . .
C12 C -0.56955(17) -0.46088(10) -0.73313(14) 0.0192(4) Uani 1 1 d . . . . .
C13 C -0.66120(18) -0.53457(10) -0.80361(15) 0.0221(4) Uani 1 1 d . . . . .
H13 H -0.636566 -0.551688 -0.881456 0.027 Uiso 1 1 calc R U . . .
C14 C -0.54561(18) -0.55325(10) -0.68555(16) 0.0235(4) Uani 1 1 d . . . . .
H14A H -0.461258 -0.582919 -0.694764 0.028 Uiso 1 1 calc R U . . .
H14B H -0.573478 -0.568160 -0.609364 0.028 Uiso 1 1 calc R U . . .
C15 C -0.31253(18) -0.43664(11) -0.75233(17) 0.0275(4) Uani 1 1 d . . . . .
H15 H -0.294745 -0.499223 -0.751727 0.033 Uiso 1 1 calc R U . . .
C16 C -0.26660(18) -0.39336(12) -0.62135(17) 0.0285(4) Uani 1 1 d . . . . .
H16A H -0.165176 -0.398598 -0.581502 0.034 Uiso 1 1 calc R U . . .
H16B H -0.320222 -0.413849 -0.564107 0.034 Uiso 1 1 calc R U . . .
C17 C -0.31005(18) -0.30194(11) -0.67195(16) 0.0260(4) Uani 1 1 d . . . . .
H17 H -0.294133 -0.256724 -0.606502 0.031 Uiso 1 1 calc R U . . .
C18 C -0.2223(2) -0.29160(12) -0.76807(18) 0.0323(4) Uani 1 1 d . . . . .
H18A H -0.124543 -0.275894 -0.726068 0.039 Uiso 1 1 calc R U . . .
H18B H -0.263399 -0.248053 -0.831530 0.039 Uiso 1 1 calc R U . . .
C19 C -0.2310(2) -0.38308(12) -0.82835(19) 0.0359(5) Uani 1 1 d . . . . .
H19A H -0.282175 -0.381443 -0.917896 0.043 Uiso 1 1 calc R U . . .
H19B H -0.136703 -0.406779 -0.819425 0.043 Uiso 1 1 calc R U . . .
C20 C -0.81500(18) -0.54667(10) -0.81208(16) 0.0250(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C20 1.3397(19) . ?
F2 C20 1.339(2) . ?
F3 C20 1.3404(19) . ?
O1 C9 1.2339(19) . ?
O2 C6 1.3837(18) . ?
O2 C7 1.3506(19) . ?
C1 C2 1.401(2) . ?
C1 C6 1.394(2) . ?
C1 C9 1.481(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C7 C8 1.343(2) . ?
C7 C12 1.478(2) . ?
C8 C9 1.444(2) . ?
C8 C10 1.499(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.575(2) . ?
C10 C17 1.549(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.541(2) . ?
C11 C15 1.531(2) . ?
C12 C13 1.519(2) . ?
C12 C14 1.512(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.493(2) . ?
C13 C20 1.489(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9800 . ?
C15 C16 1.531(2) . ?
C15 C19 1.536(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.531(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.531(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.549(3) . ?
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 O2 C6 116.63(12) . . ?
C2 C1 C9 122.10(15) . . ?
C6 C1 C2 117.13(15) . . ?
C6 C1 C9 120.75(14) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.23(15) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.12(15) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.29(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.95(15) . . ?
C6 C5 H5 120.5 . . ?
O2 C6 C1 121.92(14) . . ?
O2 C6 C5 115.83(14) . . ?
C5 C6 C1 122.25(14) . . ?
O2 C7 C12 119.74(13) . . ?
C8 C7 O2 126.32(14) . . ?
C8 C7 C12 113.94(14) . . ?
C7 C8 C9 120.65(15) . . ?
C7 C8 C10 111.12(14) . . ?
C9 C8 C10 128.17(14) . . ?
O1 C9 C1 122.26(15) . . ?
O1 C9 C8 124.27(15) . . ?
C8 C9 C1 113.46(14) . . ?
C8 C10 H10 111.4 . . ?
C8 C10 C11 104.36(12) . . ?
C8 C10 C17 115.02(13) . . ?
C11 C10 H10 111.4 . . ?
C17 C10 H10 111.4 . . ?
C17 C10 C11 102.79(13) . . ?
C10 C11 H11 110.9 . . ?
C12 C11 C10 105.69(12) . . ?
C12 C11 H11 110.9 . . ?
C15 C11 C10 102.46(13) . . ?
C15 C11 H11 110.9 . . ?
C15 C11 C12 115.48(14) . . ?
C7 C12 C11 104.75(13) . . ?
C7 C12 C13 123.00(14) . . ?
C7 C12 C14 120.83(14) . . ?
C13 C12 C11 120.08(13) . . ?
C14 C12 C11 124.49(14) . . ?
C14 C12 C13 58.99(11) . . ?
C12 C13 H13 113.1 . . ?
C14 C13 C12 60.26(10) . . ?
C14 C13 H13 113.1 . . ?
C20 C13 C12 124.72(14) . . ?
C20 C13 H13 113.1 . . ?
C20 C13 C14 122.81(15) . . ?
C12 C14 H14A 117.7 . . ?
C12 C14 H14B 117.7 . . ?
C13 C14 C12 60.75(10) . . ?
C13 C14 H14A 117.7 . . ?
C13 C14 H14B 117.7 . . ?
H14A C14 H14B 114.8 . . ?
C11 C15 H15 114.6 . . ?
C11 C15 C19 108.23(15) . . ?
C16 C15 C11 101.33(13) . . ?
C16 C15 H15 114.6 . . ?
C16 C15 C19 101.95(14) . . ?
C19 C15 H15 114.6 . . ?
C15 C16 H16A 112.8 . . ?
C15 C16 H16B 112.8 . . ?
C15 C16 C17 94.69(13) . . ?
H16A C16 H16B 110.2 . . ?
C17 C16 H16A 112.8 . . ?
C17 C16 H16B 112.8 . . ?
C10 C17 H17 114.7 . . ?
C16 C17 C10 102.28(13) . . ?
C16 C17 H17 114.7 . . ?
C16 C17 C18 101.05(14) . . ?
C18 C17 C10 107.83(14) . . ?
C18 C17 H17 114.7 . . ?
C17 C18 H18A 111.2 . . ?
C17 C18 H18B 111.2 . . ?
C17 C18 C19 102.69(14) . . ?
H18A C18 H18B 109.1 . . ?
C19 C18 H18A 111.2 . . ?
C19 C18 H18B 111.2 . . ?
C15 C19 C18 103.70(14) . . ?
C15 C19 H19A 111.0 . . ?
C15 C19 H19B 111.0 . . ?
C18 C19 H19A 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
F1 C20 F3 106.08(14) . . ?
F1 C20 C13 112.74(14) . . ?
F2 C20 F1 106.24(14) . . ?
F2 C20 F3 105.87(13) . . ?
F2 C20 C13 114.62(14) . . ?
F3 C20 C13 110.69(14) . . ?

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
O2 C7 C8 C9 -5.4(3) . . . . ?
O2 C7 C8 C10 177.16(14) . . . . ?
O2 C7 C12 C11 -179.85(13) . . . . ?
O2 C7 C12 C13 38.1(2) . . . . ?
O2 C7 C12 C14 -32.8(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C1 C6 O2 177.60(14) . . . . ?
C2 C1 C6 C5 -2.5(2) . . . . ?
C2 C1 C9 O1 1.5(2) . . . . ?
C2 C1 C9 C8 -178.45(14) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 O2 -178.78(14) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C6 O2 C7 C8 4.7(2) . . . . ?
C6 O2 C7 C12 -176.11(13) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
C6 C1 C9 O1 -177.05(16) . . . . ?
C6 C1 C9 C8 2.9(2) . . . . ?
C7 O2 C6 C1 0.0(2) . . . . ?
C7 O2 C6 C5 -179.89(14) . . . . ?
C7 C8 C9 O1 -178.68(16) . . . . ?
C7 C8 C9 C1 1.3(2) . . . . ?
C7 C8 C10 C11 3.68(17) . . . . ?
C7 C8 C10 C17 -108.14(16) . . . . ?
C7 C12 C13 C14 -108.82(17) . . . . ?
C7 C12 C13 C20 2.5(2) . . . . ?
C7 C12 C14 C13 112.42(16) . . . . ?
C8 C7 C12 C11 -0.58(18) . . . . ?
C8 C7 C12 C13 -142.67(15) . . . . ?
C8 C7 C12 C14 146.46(15) . . . . ?
C8 C10 C11 C12 -3.83(16) . . . . ?
C8 C10 C11 C15 -125.14(13) . . . . ?
C8 C10 C17 C16 81.56(16) . . . . ?
C8 C10 C17 C18 -172.41(14) . . . . ?
C9 C1 C2 C3 -176.91(15) . . . . ?
C9 C1 C6 O2 -3.7(2) . . . . ?
C9 C1 C6 C5 176.20(15) . . . . ?
C9 C8 C10 C11 -173.47(15) . . . . ?
C9 C8 C10 C17 74.7(2) . . . . ?
C10 C8 C9 O1 -1.8(3) . . . . ?
C10 C8 C9 C1 178.22(15) . . . . ?
C10 C11 C12 C7 2.77(16) . . . . ?
C10 C11 C12 C13 146.22(14) . . . . ?
C10 C11 C12 C14 -142.71(15) . . . . ?
C10 C11 C15 C16 39.11(16) . . . . ?
C10 C11 C15 C19 -67.65(16) . . . . ?
C10 C17 C18 C19 -68.35(18) . . . . ?
C11 C10 C17 C16 -31.18(16) . . . . ?
C11 C10 C17 C18 74.85(16) . . . . ?
C11 C12 C13 C14 114.55(17) . . . . ?
C11 C12 C13 C20 -134.15(17) . . . . ?
C11 C12 C14 C13 -107.25(17) . . . . ?
C11 C15 C16 C17 -57.66(15) . . . . ?
C11 C15 C19 C18 74.93(17) . . . . ?
C12 C7 C8 C9 175.34(14) . . . . ?
C12 C7 C8 C10 -2.05(19) . . . . ?
C12 C11 C15 C16 -75.22(17) . . . . ?
C12 C11 C15 C19 178.02(13) . . . . ?
C12 C13 C20 F1 54.8(2) . . . . ?
C12 C13 C20 F2 -66.9(2) . . . . ?
C12 C13 C20 F3 173.41(14) . . . . ?
C14 C12 C13 C20 111.30(18) . . . . ?
C14 C13 C20 F1 129.02(16) . . . . ?
C14 C13 C20 F2 7.3(2) . . . . ?
C14 C13 C20 F3 -112.34(17) . . . . ?
C15 C11 C12 C7 115.23(15) . . . . ?
C15 C11 C12 C13 -101.32(17) . . . . ?
C15 C11 C12 C14 -30.2(2) . . . . ?
C15 C16 C17 C10 54.29(15) . . . . ?
C15 C16 C17 C18 -56.92(15) . . . . ?
C16 C15 C19 C18 -31.39(18) . . . . ?
C16 C17 C18 C19 38.54(17) . . . . ?
C17 C10 C11 C12 116.55(13) . . . . ?
C17 C10 C11 C15 -4.76(16) . . . . ?
C17 C18 C19 C15 -4.31(19) . . . . ?
C19 C15 C16 C17 53.96(15) . . . . ?
C20 C13 C14 C12 -114.34(17) . . . . ?

_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 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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_89-6a
_database_code_depnum_ccdc_archive 'CCDC 2077701'
loop_
_audit_author_name
_audit_author_address
Han
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-12-05
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O2, C23 H24 O2'
_chemical_formula_sum            'C39 H40 O4'
_chemical_formula_weight         572.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   19.8900(14)
_cell_length_b                   6.5408(4)
_cell_length_c                   23.4265(19)
_cell_angle_alpha                90
_cell_angle_beta                 102.826(7)
_cell_angle_gamma                90
_cell_volume                     2971.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2272
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.9050
_cell_measurement_theta_min      3.2780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10226
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  79.00   1.00    2.00    --   41.11 -99.00-120.00   53
  2  ω     35.00  89.00   1.00    2.50    --  107.58 -61.00 -90.00   54
  3  ω    106.00 133.00   1.00    2.50    --  107.58 -61.00 -90.00   27
  4  ω     96.00 178.00   1.00    2.50    --  107.58  45.00  60.00   82
  5  ω    130.00 161.00   1.00    2.50    --  107.58 125.00 -90.00   31
  6  ω     91.00 154.00   1.00    2.50    --  107.58  45.00   0.00   63
  7  ω     36.00 135.00   1.00    2.50    --  107.58 -30.00  30.00   99
  8  ω     25.00  90.00   1.00    2.50    --  107.58 -95.00-150.00   65
  9  ω   -113.00 -31.00   1.00    2.00    --  -41.11 -38.00 -90.00   82
 10  ω   -121.00  -6.00   1.00    2.00    --  -41.11 -19.00 150.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0615568000
_diffrn_orient_matrix_UB_12      0.0878731000
_diffrn_orient_matrix_UB_13      -0.0451915000
_diffrn_orient_matrix_UB_21      0.0339914000
_diffrn_orient_matrix_UB_22      -0.0661233000
_diffrn_orient_matrix_UB_23      -0.0500424000
_diffrn_orient_matrix_UB_31      -0.0369239000
_diffrn_orient_matrix_UB_32      -0.2081148000
_diffrn_orient_matrix_UB_33      -0.0030641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3875
_reflns_number_total             5241
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.024
_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)+(0.1154P)²+1.9872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2001
_refine_ls_wR_factor_ref         0.2243
_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:
 C10(H10), C12(H12), C14(H14), C26(H26), C27(H27), C30(H30), C31(H31), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C28(H28A,
 H28B), C29(H29A,H29B), C32(H32A,H32B), C36(H36A,H36B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C18(H18), C19(H19), C20(H20),
 C21(H21), C25(H25), C34(H34), C35(H35)
2.d X=CH2 refined with riding coordinates:
 C39(H39A,H39B)
;
_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 0.54124(13) 0.8049(3) 0.86960(12) 0.0542(7) Uani 1 1 d . . . . .
O2 O 0.44592(10) 0.2748(3) 0.89734(9) 0.0374(5) Uani 1 1 d . . . . .
C1 C 0.46704(14) 0.6306(4) 0.91966(13) 0.0323(6) Uani 1 1 d . . . . .
C2 C 0.45350(15) 0.8001(5) 0.95219(13) 0.0369(7) Uani 1 1 d . . . . .
H2 H 0.474749 0.924424 0.948381 0.044 Uiso 1 1 calc R U . . .
C3 C 0.40943(15) 0.7851(5) 0.98946(13) 0.0389(7) Uani 1 1 d . . . . .
H3 H 0.401699 0.897733 1.011362 0.047 Uiso 1 1 calc R U . . .
C4 C 0.37635(16) 0.6007(5) 0.99440(14) 0.0425(8) Uani 1 1 d . . . . .
H4 H 0.345647 0.591562 1.019008 0.051 Uiso 1 1 calc R U . . .
C5 C 0.38860(15) 0.4310(5) 0.96316(14) 0.0401(7) Uani 1 1 d . . . . .
H5 H 0.366521 0.307663 0.966481 0.048 Uiso 1 1 calc R U . . .
C6 C 0.43467(14) 0.4484(4) 0.92660(13) 0.0334(6) Uani 1 1 d . . . . .
C7 C 0.49177(15) 0.2831(5) 0.86183(13) 0.0355(7) Uani 1 1 d . . . . .
H7 H 0.500216 0.162552 0.843577 0.043 Uiso 1 1 calc R U . . .
C8 C 0.52551(14) 0.4505(4) 0.85117(12) 0.0324(6) Uani 1 1 d . . . . .
C9 C 0.51370(15) 0.6434(5) 0.87913(14) 0.0370(7) Uani 1 1 d . . . . .
C10 C 0.57592(15) 0.4542(5) 0.81167(13) 0.0363(7) Uani 1 1 d . . . . .
H10 H 0.563662 0.567627 0.783971 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5825(2) 0.2581(6) 0.77681(19) 0.0599(11) Uani 1 1 d . . . . .
H11A H 0.556133 0.147771 0.788829 0.072 Uiso 1 1 calc R U . . .
H11B H 0.565642 0.281440 0.735201 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6559(2) 0.2069(7) 0.7897(2) 0.0712(12) Uani 1 1 d . . . . .
H12 H 0.665304 0.065375 0.780113 0.085 Uiso 1 1 calc R U . . .
C13 C 0.6728(2) 0.2510(8) 0.85390(18) 0.0767(14) Uani 1 1 d . . . . .
H13A H 0.721317 0.233043 0.871661 0.092 Uiso 1 1 calc R U . . .
H13B H 0.644797 0.172683 0.875084 0.092 Uiso 1 1 calc R U . . .
C14 C 0.65059(16) 0.4862(6) 0.84655(14) 0.0461(8) Uani 1 1 d . . . . .
H14 H 0.656072 0.565282 0.882814 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6938(2) 0.5529(7) 0.8050(2) 0.0717(12) Uani 1 1 d . . . . .
H15A H 0.739013 0.597322 0.826194 0.086 Uiso 1 1 calc R U . . .
H15B H 0.671822 0.664499 0.780519 0.086 Uiso 1 1 calc R U . . .
C16 C 0.6997(2) 0.3609(6) 0.76737(18) 0.0594(10) Uani 1 1 d . . . . .
H16A H 0.682105 0.388064 0.726051 0.071 Uiso 1 1 calc R U . . .
H16B H 0.747153 0.314822 0.773442 0.071 Uiso 1 1 calc R U . . .
O3 O 0.38813(11) 0.9219(3) 0.76826(9) 0.0403(5) Uani 1 1 d . . . . .
O4 O 0.40216(12) 0.3517(3) 0.70116(10) 0.0436(6) Uani 1 1 d . . . . .
C17 C 0.35353(15) 0.7632(5) 0.78659(13) 0.0350(7) Uani 1 1 d . . . . .
C18 C 0.31508(16) 0.8081(5) 0.82824(13) 0.0415(7) Uani 1 1 d . . . . .
H18 H 0.314658 0.939777 0.843147 0.050 Uiso 1 1 calc R U . . .
C19 C 0.27833(16) 0.6561(6) 0.84658(14) 0.0440(8) Uani 1 1 d . . . . .
H19 H 0.252067 0.684594 0.873869 0.053 Uiso 1 1 calc R U . . .
C20 C 0.27954(16) 0.4567(5) 0.82484(14) 0.0438(8) Uani 1 1 d . . . . .
H20 H 0.254048 0.354206 0.837685 0.053 Uiso 1 1 calc R U . . .
C21 C 0.31828(15) 0.4124(5) 0.78463(13) 0.0378(7) Uani 1 1 d . . . . .
H21 H 0.319329 0.279546 0.770698 0.045 Uiso 1 1 calc R U . . .
C22 C 0.35621(14) 0.5664(4) 0.76450(12) 0.0319(6) Uani 1 1 d . . . . .
C23 C 0.39687(14) 0.5260(4) 0.72054(12) 0.0328(6) Uani 1 1 d . . . . .
C24 C 0.42932(14) 0.7028(4) 0.70091(13) 0.0339(6) Uani 1 1 d . . . . .
C25 C 0.42322(16) 0.8859(5) 0.72594(13) 0.0376(7) Uani 1 1 d . . . . .
H25 H 0.445005 0.996861 0.712983 0.045 Uiso 1 1 calc R U . . .
C26 C 0.47028(15) 0.6736(5) 0.65429(14) 0.0367(7) Uani 1 1 d . . . . .
H26 H 0.488607 0.534052 0.658782 0.044 Uiso 1 1 calc R U . . .
C27 C 0.53289(16) 0.8182(6) 0.65837(16) 0.0495(9) Uani 1 1 d . . . . .
H27 H 0.552309 0.870931 0.697733 0.059 Uiso 1 1 calc R U . . .
C28 C 0.58470(18) 0.7117(7) 0.62940(18) 0.0640(11) Uani 1 1 d . . . . .
H28A H 0.595132 0.575205 0.645050 0.077 Uiso 1 1 calc R U . . .
H28B H 0.627162 0.789379 0.634538 0.077 Uiso 1 1 calc R U . . .
C29 C 0.54639(18) 0.7044(7) 0.56405(17) 0.0579(10) Uani 1 1 d . . . . .
H29A H 0.573908 0.765688 0.539180 0.070 Uiso 1 1 calc R U . . .
H29B H 0.535087 0.565037 0.551347 0.070 Uiso 1 1 calc R U . . .
C30 C 0.48065(16) 0.8307(6) 0.56322(16) 0.0491(9) Uani 1 1 d . . . . .
H30 H 0.460499 0.893517 0.525306 0.059 Uiso 1 1 calc R U . . .
C31 C 0.43013(15) 0.6965(5) 0.58804(14) 0.0389(7) Uani 1 1 d . . . . .
H31 H 0.426952 0.561935 0.569218 0.047 Uiso 1 1 calc R U . . .
C32 C 0.50463(19) 0.9830(6) 0.61264(17) 0.0550(9) Uani 1 1 d . . . . .
H32A H 0.466960 1.060421 0.622120 0.066 Uiso 1 1 calc R U . . .
H32B H 0.540131 1.074692 0.605362 0.066 Uiso 1 1 calc R U . . .
C33 C 0.35636(15) 0.7901(5) 0.57854(14) 0.0399(7) Uani 1 1 d . . . . .
H33 H 0.356848 0.893479 0.608921 0.048 Uiso 1 1 calc R U . . .
C34 C 0.30460(16) 0.6276(5) 0.58501(15) 0.0438(8) Uani 1 1 d . . . . .
H34 H 0.306003 0.575205 0.622164 0.053 Uiso 1 1 calc R U . . .
C35 C 0.25742(17) 0.5558(6) 0.54067(16) 0.0514(9) Uani 1 1 d . . . . .
H35 H 0.227248 0.457490 0.549069 0.062 Uiso 1 1 calc R U . . .
C36 C 0.2486(2) 0.6188(7) 0.47877(17) 0.0633(11) Uani 1 1 d . . . . .
H36A H 0.207152 0.700806 0.467363 0.076 Uiso 1 1 calc R U . . .
H36B H 0.243170 0.498317 0.454027 0.076 Uiso 1 1 calc R U . . .
C37 C 0.3112(2) 0.7433(8) 0.46968(16) 0.0677(12) Uani 1 1 d . . . . .
H37A H 0.349280 0.652146 0.468326 0.081 Uiso 1 1 calc R U . . .
H37B H 0.299319 0.816893 0.432860 0.081 Uiso 1 1 calc R U . . .
C38 C 0.33205(18) 0.8919(6) 0.51947(17) 0.0527(9) Uani 1 1 d . . . . .
C39 C 0.3260(2) 1.0921(7) 0.5139(2) 0.0730(13) Uani 1 1 d . . . . .
H39A H 0.307865 1.149609 0.477453 0.088 Uiso 1 1 calc R U . . .
H39B H 0.339876 1.175851 0.546510 0.088 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 C9 1.233(4) . ?
O2 C6 1.370(3) . ?
O2 C7 1.365(4) . ?
C1 C2 1.405(4) . ?
C1 C6 1.381(4) . ?
C1 C9 1.470(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.336(4) . ?
C8 C9 1.464(4) . ?
C8 C10 1.508(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.542(4) . ?
C10 C14 1.542(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.463(6) . ?
C12 H12 0.9800 . ?
C12 C13 1.495(6) . ?
C12 C16 1.499(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.599(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.500(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.554(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O3 C17 1.366(4) . ?
O3 C25 1.354(4) . ?
O4 C23 1.240(4) . ?
C17 C18 1.398(4) . ?
C17 C22 1.393(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.359(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.402(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.401(4) . ?
C22 C23 1.468(4) . ?
C23 C24 1.448(4) . ?
C24 C25 1.351(4) . ?
C24 C26 1.513(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9800 . ?
C26 C27 1.550(4) . ?
C26 C31 1.587(4) . ?
C27 H27 0.9800 . ?
C27 C28 1.523(5) . ?
C27 C32 1.536(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.552(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.543(5) . ?
C30 H30 0.9800 . ?
C30 C31 1.542(4) . ?
C30 C32 1.522(5) . ?
C31 H31 0.9800 . ?
C31 C33 1.560(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33 0.9800 . ?
C33 C34 1.511(5) . ?
C33 C38 1.515(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.322(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.480(5) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.542(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.504(6) . ?
C38 C39 1.319(6) . ?
C39 H39A 0.9300 . ?
C39 H39B 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
C7 O2 C6 118.5(2) . . ?
C2 C1 C9 122.0(3) . . ?
C6 C1 C2 117.8(3) . . ?
C6 C1 C9 120.2(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
O2 C6 C1 121.6(3) . . ?
O2 C6 C5 116.3(3) . . ?
C1 C6 C5 122.1(3) . . ?
O2 C7 H7 117.4 . . ?
C8 C7 O2 125.3(3) . . ?
C8 C7 H7 117.4 . . ?
C7 C8 C9 119.0(3) . . ?
C7 C8 C10 123.9(3) . . ?
C9 C8 C10 117.1(3) . . ?
O1 C9 C1 122.4(3) . . ?
O1 C9 C8 122.4(3) . . ?
C8 C9 C1 115.3(3) . . ?
C8 C10 H10 108.5 . . ?
C8 C10 C11 117.3(3) . . ?
C8 C10 C14 111.7(2) . . ?
C11 C10 H10 108.5 . . ?
C11 C10 C14 102.0(3) . . ?
C14 C10 H10 108.5 . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C12 C11 C10 106.2(3) . . ?
C12 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
C11 C12 H12 113.6 . . ?
C11 C12 C13 98.8(3) . . ?
C11 C12 C16 113.9(4) . . ?
C13 C12 H12 113.6 . . ?
C13 C12 C16 101.7(4) . . ?
C16 C12 H12 113.6 . . ?
C12 C13 H13A 112.8 . . ?
C12 C13 H13B 112.8 . . ?
C12 C13 C14 94.7(3) . . ?
H13A C13 H13B 110.2 . . ?
C14 C13 H13A 112.8 . . ?
C14 C13 H13B 112.8 . . ?
C10 C14 C13 97.9(3) . . ?
C10 C14 H14 116.1 . . ?
C13 C14 H14 116.1 . . ?
C15 C14 C10 108.6(3) . . ?
C15 C14 C13 99.5(3) . . ?
C15 C14 H14 116.1 . . ?
C14 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
C14 C15 C16 105.0(3) . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C12 C16 C15 102.9(3) . . ?
C12 C16 H16A 111.2 . . ?
C12 C16 H16B 111.2 . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
C25 O3 C17 118.4(2) . . ?
O3 C17 C18 116.8(3) . . ?
O3 C17 C22 121.5(3) . . ?
C22 C17 C18 121.7(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(3) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 118.1(3) . . ?
C17 C22 C23 120.0(3) . . ?
C21 C22 C23 121.9(3) . . ?
O4 C23 C22 121.8(3) . . ?
O4 C23 C24 122.5(3) . . ?
C24 C23 C22 115.7(3) . . ?
C23 C24 C26 118.5(3) . . ?
C25 C24 C23 118.7(3) . . ?
C25 C24 C26 122.7(3) . . ?
O3 C25 H25 117.2 . . ?
C24 C25 O3 125.6(3) . . ?
C24 C25 H25 117.2 . . ?
C24 C26 H26 106.7 . . ?
C24 C26 C27 115.6(3) . . ?
C24 C26 C31 117.3(2) . . ?
C27 C26 H26 106.7 . . ?
C27 C26 C31 103.1(2) . . ?
C31 C26 H26 106.7 . . ?
C26 C27 H27 114.6 . . ?
C28 C27 C26 107.9(3) . . ?
C28 C27 H27 114.6 . . ?
C28 C27 C32 100.9(3) . . ?
C32 C27 C26 102.7(3) . . ?
C32 C27 H27 114.6 . . ?
C27 C28 H28A 111.2 . . ?
C27 C28 H28B 111.2 . . ?
C27 C28 C29 102.8(3) . . ?
H28A C28 H28B 109.1 . . ?
C29 C28 H28A 111.2 . . ?
C29 C28 H28B 111.2 . . ?
C28 C29 H29A 111.2 . . ?
C28 C29 H29B 111.2 . . ?
H29A C29 H29B 109.1 . . ?
C30 C29 C28 103.0(3) . . ?
C30 C29 H29A 111.2 . . ?
C30 C29 H29B 111.2 . . ?
C29 C30 H30 114.3 . . ?
C31 C30 C29 108.2(3) . . ?
C31 C30 H30 114.3 . . ?
C32 C30 C29 102.7(3) . . ?
C32 C30 H30 114.3 . . ?
C32 C30 C31 101.9(3) . . ?
C26 C31 H31 108.9 . . ?
C30 C31 C26 101.2(2) . . ?
C30 C31 H31 108.9 . . ?
C30 C31 C33 113.2(3) . . ?
C33 C31 C26 115.5(2) . . ?
C33 C31 H31 108.9 . . ?
C27 C32 H32A 112.9 . . ?
C27 C32 H32B 112.9 . . ?
C30 C32 C27 94.3(3) . . ?
C30 C32 H32A 112.9 . . ?
C30 C32 H32B 112.9 . . ?
H32A C32 H32B 110.3 . . ?
C31 C33 H33 108.1 . . ?
C34 C33 C31 110.5(3) . . ?
C34 C33 H33 108.1 . . ?
C34 C33 C38 108.3(3) . . ?
C38 C33 C31 113.7(3) . . ?
C38 C33 H33 108.1 . . ?
C33 C34 H34 118.3 . . ?
C35 C34 C33 123.5(3) . . ?
C35 C34 H34 118.3 . . ?
C34 C35 H35 117.3 . . ?
C34 C35 C36 125.5(4) . . ?
C36 C35 H35 117.3 . . ?
C35 C36 H36A 109.4 . . ?
C35 C36 H36B 109.4 . . ?
C35 C36 C37 111.0(3) . . ?
H36A C36 H36B 108.0 . . ?
C37 C36 H36A 109.4 . . ?
C37 C36 H36B 109.4 . . ?
C36 C37 H37A 109.9 . . ?
C36 C37 H37B 109.9 . . ?
H37A C37 H37B 108.3 . . ?
C38 C37 C36 109.0(3) . . ?
C38 C37 H37A 109.9 . . ?
C38 C37 H37B 109.9 . . ?
C37 C38 C33 113.7(3) . . ?
C39 C38 C33 122.0(4) . . ?
C39 C38 C37 124.2(4) . . ?
C38 C39 H39A 120.0 . . ?
C38 C39 H39B 120.0 . . ?
H39A C39 H39B 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
O2 C7 C8 C9 0.1(5) . . . . ?
O2 C7 C8 C10 180.0(3) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C2 C1 C6 O2 -178.8(2) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
C2 C1 C9 O1 -3.1(5) . . . . ?
C2 C1 C9 C8 176.5(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 O2 178.9(3) . . . . ?
C4 C5 C6 C1 -1.6(4) . . . . ?
C6 O2 C7 C8 -2.6(4) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C1 C9 O1 176.7(3) . . . . ?
C6 C1 C9 C8 -3.7(4) . . . . ?
C7 O2 C6 C1 1.8(4) . . . . ?
C7 O2 C6 C5 -178.7(2) . . . . ?
C7 C8 C9 O1 -177.4(3) . . . . ?
C7 C8 C9 C1 3.0(4) . . . . ?
C7 C8 C10 C11 6.7(4) . . . . ?
C7 C8 C10 C14 -110.5(3) . . . . ?
C8 C10 C11 C12 -126.8(3) . . . . ?
C8 C10 C14 C13 94.5(3) . . . . ?
C8 C10 C14 C15 -162.6(3) . . . . ?
C9 C1 C2 C3 179.6(3) . . . . ?
C9 C1 C6 O2 1.4(4) . . . . ?
C9 C1 C6 C5 -178.1(3) . . . . ?
C9 C8 C10 C11 -173.4(3) . . . . ?
C9 C8 C10 C14 69.4(3) . . . . ?
C10 C8 C9 O1 2.7(4) . . . . ?
C10 C8 C9 C1 -176.9(2) . . . . ?
C10 C11 C12 C13 41.6(4) . . . . ?
C10 C11 C12 C16 -65.5(5) . . . . ?
C10 C14 C15 C16 -70.4(4) . . . . ?
C11 C10 C14 C13 -31.5(3) . . . . ?
C11 C10 C14 C15 71.4(4) . . . . ?
C11 C12 C13 C14 -59.9(4) . . . . ?
C11 C12 C16 C15 66.4(5) . . . . ?
C12 C13 C14 C10 56.5(3) . . . . ?
C12 C13 C14 C15 -54.0(4) . . . . ?
C13 C12 C16 C15 -38.8(4) . . . . ?
C13 C14 C15 C16 31.3(4) . . . . ?
C14 C10 C11 C12 -4.4(4) . . . . ?
C14 C15 C16 C12 2.8(5) . . . . ?
C16 C12 C13 C14 56.9(3) . . . . ?
O3 C17 C18 C19 178.3(3) . . . . ?
O3 C17 C22 C21 -178.8(3) . . . . ?
O3 C17 C22 C23 0.0(4) . . . . ?
O4 C23 C24 C25 -177.4(3) . . . . ?
O4 C23 C24 C26 1.0(4) . . . . ?
C17 O3 C25 C24 -2.4(4) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C17 C22 C23 O4 177.8(3) . . . . ?
C17 C22 C23 C24 -3.0(4) . . . . ?
C18 C17 C22 C21 0.8(4) . . . . ?
C18 C17 C22 C23 179.6(3) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 C22 -0.8(5) . . . . ?
C20 C21 C22 C17 0.3(4) . . . . ?
C20 C21 C22 C23 -178.5(3) . . . . ?
C21 C22 C23 O4 -3.4(4) . . . . ?
C21 C22 C23 C24 175.7(3) . . . . ?
C22 C17 C18 C19 -1.4(4) . . . . ?
C22 C23 C24 C25 3.4(4) . . . . ?
C22 C23 C24 C26 -178.2(2) . . . . ?
C23 C24 C25 O3 -0.8(5) . . . . ?
C23 C24 C26 C27 -147.7(3) . . . . ?
C23 C24 C26 C31 90.2(3) . . . . ?
C24 C26 C27 C28 154.3(3) . . . . ?
C24 C26 C27 C32 -99.6(3) . . . . ?
C24 C26 C31 C30 134.6(3) . . . . ?
C24 C26 C31 C33 12.0(4) . . . . ?
C25 O3 C17 C18 -176.9(3) . . . . ?
C25 O3 C17 C22 2.7(4) . . . . ?
C25 C24 C26 C27 30.6(4) . . . . ?
C25 C24 C26 C31 -91.4(4) . . . . ?
C26 C24 C25 O3 -179.2(3) . . . . ?
C26 C27 C28 C29 67.2(4) . . . . ?
C26 C27 C32 C30 -53.8(3) . . . . ?
C26 C31 C33 C34 -82.6(3) . . . . ?
C26 C31 C33 C38 155.3(3) . . . . ?
C27 C26 C31 C30 6.3(3) . . . . ?
C27 C26 C31 C33 -116.3(3) . . . . ?
C27 C28 C29 C30 6.3(4) . . . . ?
C28 C27 C32 C30 57.6(3) . . . . ?
C28 C29 C30 C31 -77.1(4) . . . . ?
C28 C29 C30 C32 30.1(4) . . . . ?
C29 C30 C31 C26 67.0(3) . . . . ?
C29 C30 C31 C33 -168.9(3) . . . . ?
C29 C30 C32 C27 -53.5(3) . . . . ?
C30 C31 C33 C34 161.4(3) . . . . ?
C30 C31 C33 C38 39.4(4) . . . . ?
C31 C26 C27 C28 -76.3(3) . . . . ?
C31 C26 C27 C32 29.7(3) . . . . ?
C31 C30 C32 C27 58.5(3) . . . . ?
C31 C33 C34 C35 -109.5(4) . . . . ?
C31 C33 C38 C37 75.1(4) . . . . ?
C31 C33 C38 C39 -109.0(4) . . . . ?
C32 C27 C28 C29 -40.1(4) . . . . ?
C32 C30 C31 C26 -40.8(3) . . . . ?
C32 C30 C31 C33 83.4(3) . . . . ?
C33 C34 C35 C36 1.1(6) . . . . ?
C34 C33 C38 C37 -48.2(4) . . . . ?
C34 C33 C38 C39 127.7(4) . . . . ?
C34 C35 C36 C37 12.8(6) . . . . ?
C35 C36 C37 C38 -42.6(5) . . . . ?
C36 C37 C38 C33 63.5(4) . . . . ?
C36 C37 C38 C39 -112.2(4) . . . . ?
C38 C33 C34 C35 15.7(4) . . . . ?

_olex2_date_sample_data_collection 2020-12-05
_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 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.522
####################################################################### 
# 
# 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_187-2
_database_code_depnum_ccdc_archive 'CCDC 2058540'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2021-01-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CY-101
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           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                   8.2978(4)
_cell_length_b                   11.1917(5)
_cell_length_c                   32.354(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3004.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2167
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3990
_cell_measurement_theta_min      2.6810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            6145
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.579
_diffrn_reflns_theta_max         66.579
_diffrn_reflns_theta_min         2.731
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  65.00   1.00    1.59    --   40.73 -38.00  30.00   85
  2  ω     82.00 141.00   1.00    3.00    --  107.58  45.00 120.00   59
  3  ω    116.00 168.00   1.00    3.00    --  107.58 125.00 150.00   52
  4  ω     82.00 178.00   1.00    3.00    --  107.58  61.00 -30.00   96
  5  ω    142.00 167.00   1.00    3.00    --  107.58 125.00-150.00   25
  6  ω     98.00 124.00   1.00    3.00    --  107.58 125.00-150.00   26
  7  ω   -112.00 -46.00   1.00    1.59    --  -40.73 -57.00-120.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0014926000
_diffrn_orient_matrix_UB_12      -0.1184492000
_diffrn_orient_matrix_UB_13      -0.0242255000
_diffrn_orient_matrix_UB_21      -0.0650136000
_diffrn_orient_matrix_UB_22      -0.0657217000
_diffrn_orient_matrix_UB_23      0.0383291000
_diffrn_orient_matrix_UB_31      -0.1740831000
_diffrn_orient_matrix_UB_32      0.0237409000
_diffrn_orient_matrix_UB_33      -0.0145376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2192
_reflns_number_total             2641
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.066
_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)+(0.0363P)²+2.9448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1253
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0287(2) 0.79118(15) 0.71095(6) 0.0370(4) Uani 1 1 d . . . . .
H1 H 0.046986 0.811264 0.696199 0.055 Uiso 1 1 calc R U . . .
O2 O 0.1906(2) 0.76358(15) 0.65586(5) 0.0328(4) Uani 1 1 d . . . . .
O3 O 0.15722(19) 0.57788(14) 0.51603(5) 0.0290(4) Uani 1 1 d . . . . .
O4 O 0.1144(2) 0.38259(14) 0.52435(6) 0.0320(4) Uani 1 1 d . . . . .
H4 H 0.030130 0.399093 0.512390 0.048 Uiso 1 1 calc R U . . .
C1 C 0.0389(3) 0.6001(2) 0.68060(7) 0.0223(5) Uani 1 1 d . . . . .
C2 C -0.0509(3) 0.6723(2) 0.70790(7) 0.0277(5) Uani 1 1 d . . . . .
C3 C -0.1686(3) 0.6209(3) 0.73291(8) 0.0349(6) Uani 1 1 d . . . . .
H3 H -0.227805 0.668705 0.750864 0.042 Uiso 1 1 calc R U . . .
C4 C -0.1979(3) 0.5003(3) 0.73127(8) 0.0354(6) Uani 1 1 d . . . . .
H4A H -0.278025 0.467157 0.747775 0.043 Uiso 1 1 calc R U . . .
C5 C -0.1085(3) 0.4272(2) 0.70508(7) 0.0303(5) Uani 1 1 d . . . . .
H5 H -0.127381 0.345314 0.704398 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0080(3) 0.4771(2) 0.68018(7) 0.0251(5) Uani 1 1 d . . . . .
H6 H 0.067544 0.428004 0.662701 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1607(3) 0.6557(2) 0.65358(7) 0.0230(5) Uani 1 1 d . . . . .
C8 C 0.2435(3) 0.5796(2) 0.62129(7) 0.0245(5) Uani 1 1 d . . . . .
H8A H 0.164864 0.556212 0.600626 0.029 Uiso 1 1 calc R U . . .
H8B H 0.283037 0.507290 0.634367 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3838(3) 0.6420(2) 0.59978(7) 0.0219(5) Uani 1 1 d . . . . .
H9 H 0.350563 0.722582 0.591610 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5327(3) 0.6505(2) 0.62825(7) 0.0270(5) Uani 1 1 d . . . . .
H10 H 0.507118 0.665109 0.657389 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6525(3) 0.7401(2) 0.60948(8) 0.0332(6) Uani 1 1 d . . . . .
H11A H 0.737563 0.759642 0.628893 0.040 Uiso 1 1 calc R U . . .
H11B H 0.598587 0.813017 0.601034 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7197(3) 0.6709(2) 0.57156(8) 0.0324(6) Uani 1 1 d . . . . .
H12A H 0.697124 0.713155 0.546034 0.039 Uiso 1 1 calc R U . . .
H12B H 0.835100 0.658918 0.573964 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6291(3) 0.5511(2) 0.57317(7) 0.0262(5) Uani 1 1 d . . . . .
H13 H 0.681597 0.485920 0.558078 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4517(3) 0.5737(2) 0.56070(7) 0.0215(5) Uani 1 1 d . . . . .
H14 H 0.450548 0.628784 0.537159 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6162(3) 0.5312(2) 0.62005(8) 0.0298(6) Uani 1 1 d . . . . .
H15A H 0.549744 0.462996 0.627187 0.036 Uiso 1 1 calc R U . . .
H15B H 0.720557 0.525204 0.633425 0.036 Uiso 1 1 calc R U . . .
C16 C 0.3618(3) 0.4617(2) 0.54851(7) 0.0221(5) Uani 1 1 d . . . . .
C17 C 0.4155(3) 0.3511(2) 0.55273(8) 0.0307(6) Uani 1 1 d . . . . .
H17A H 0.353(3) 0.280(2) 0.5425(8) 0.033(7) Uiso 1 1 d . . . . .
H17B H 0.520(4) 0.336(3) 0.5649(9) 0.045(8) Uiso 1 1 d . . . . .
C18 C 0.2025(3) 0.4795(2) 0.52821(7) 0.0233(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C2 1.347(3) . ?
O2 C7 1.235(3) . ?
O3 C18 1.228(3) . ?
O4 H4 0.8200 . ?
O4 C18 1.314(3) . ?
C1 C2 1.411(3) . ?
C1 C6 1.400(3) . ?
C1 C7 1.474(3) . ?
C2 C3 1.392(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(4) . ?
C4 H4A 0.9300 . ?
C4 C5 1.392(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.526(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.544(3) . ?
C9 C14 1.581(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.537(3) . ?
C10 C15 1.527(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.555(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.538(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.547(3) . ?
C13 C15 1.537(3) . ?
C14 H14 0.9800 . ?
C14 C16 1.511(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.323(3) . ?
C16 C18 1.490(3) . ?
C17 H17A 1.01(3) . ?
C17 H17B 0.97(3) . ?

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
C2 O1 H1 109.5 . . ?
C18 O4 H4 109.5 . . ?
C2 C1 C7 119.5(2) . . ?
C6 C1 C2 118.2(2) . . ?
C6 C1 C7 122.3(2) . . ?
O1 C2 C1 122.6(2) . . ?
O1 C2 C3 117.5(2) . . ?
C3 C2 C1 119.9(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4A 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
O2 C7 C1 121.0(2) . . ?
O2 C7 C8 120.0(2) . . ?
C1 C7 C8 118.87(19) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C7 C8 C9 113.81(19) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C8 C9 H9 109.2 . . ?
C8 C9 C10 111.52(19) . . ?
C8 C9 C14 114.54(18) . . ?
C10 C9 H9 109.2 . . ?
C10 C9 C14 102.84(17) . . ?
C14 C9 H9 109.2 . . ?
C9 C10 H10 114.3 . . ?
C11 C10 C9 108.79(19) . . ?
C11 C10 H10 114.3 . . ?
C15 C10 C9 101.86(18) . . ?
C15 C10 H10 114.3 . . ?
C15 C10 C11 102.00(19) . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C10 C11 C12 102.65(19) . . ?
H11A C11 H11B 109.2 . . ?
C12 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 C11 103.42(19) . . ?
C13 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C12 C13 H13 114.5 . . ?
C12 C13 C14 108.30(19) . . ?
C14 C13 H13 114.5 . . ?
C15 C13 C12 101.16(19) . . ?
C15 C13 H13 114.5 . . ?
C15 C13 C14 102.41(18) . . ?
C9 C14 H14 108.3 . . ?
C13 C14 C9 102.08(17) . . ?
C13 C14 H14 108.3 . . ?
C16 C14 C9 115.72(17) . . ?
C16 C14 C13 113.70(18) . . ?
C16 C14 H14 108.3 . . ?
C10 C15 C13 94.38(18) . . ?
C10 C15 H15A 112.9 . . ?
C10 C15 H15B 112.9 . . ?
C13 C15 H15A 112.9 . . ?
C13 C15 H15B 112.9 . . ?
H15A C15 H15B 110.3 . . ?
C17 C16 C14 125.7(2) . . ?
C17 C16 C18 118.0(2) . . ?
C18 C16 C14 116.23(19) . . ?
C16 C17 H17A 122.4(15) . . ?
C16 C17 H17B 120.6(18) . . ?
H17A C17 H17B 117(2) . . ?
O3 C18 O4 122.6(2) . . ?
O3 C18 C16 122.2(2) . . ?
O4 C18 C16 115.17(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 179.8(2) . . . . ?
O2 C7 C8 C9 11.6(3) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C7 C8 C9 -171.33(19) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C1 C7 O2 3.5(3) . . . . ?
C2 C1 C7 C8 -173.5(2) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C6 C1 C2 O1 179.1(2) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C1 C7 O2 -176.8(2) . . . . ?
C6 C1 C7 C8 6.2(3) . . . . ?
C7 C1 C2 O1 -1.1(3) . . . . ?
C7 C1 C2 C3 178.6(2) . . . . ?
C7 C1 C6 C5 -178.7(2) . . . . ?
C7 C8 C9 C10 74.2(2) . . . . ?
C7 C8 C9 C14 -169.51(18) . . . . ?
C8 C9 C10 C11 -165.92(19) . . . . ?
C8 C9 C10 C15 86.9(2) . . . . ?
C8 C9 C14 C13 -120.1(2) . . . . ?
C8 C9 C14 C16 3.9(3) . . . . ?
C9 C10 C11 C12 -72.0(2) . . . . ?
C9 C10 C15 C13 56.4(2) . . . . ?
C9 C14 C16 C17 -108.9(3) . . . . ?
C9 C14 C16 C18 74.2(2) . . . . ?
C10 C9 C14 C13 1.1(2) . . . . ?
C10 C9 C14 C16 125.1(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C10 C15 C13 -56.0(2) . . . . ?
C11 C12 C13 C14 71.7(2) . . . . ?
C11 C12 C13 C15 -35.5(2) . . . . ?
C12 C13 C14 C9 -72.1(2) . . . . ?
C12 C13 C14 C16 162.57(19) . . . . ?
C12 C13 C15 C10 55.88(19) . . . . ?
C13 C14 C16 C17 8.9(3) . . . . ?
C13 C14 C16 C18 -168.06(19) . . . . ?
C14 C9 C10 C11 70.9(2) . . . . ?
C14 C9 C10 C15 -36.3(2) . . . . ?
C14 C13 C15 C10 -55.9(2) . . . . ?
C14 C16 C18 O3 11.2(3) . . . . ?
C14 C16 C18 O4 -168.76(19) . . . . ?
C15 C10 C11 C12 35.1(2) . . . . ?
C15 C13 C14 C9 34.3(2) . . . . ?
C15 C13 C14 C16 -91.1(2) . . . . ?
C17 C16 C18 O3 -166.0(2) . . . . ?
C17 C16 C18 O4 14.1(3) . . . . ?

_olex2_date_sample_data_collection 2021-01-20
_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 2.067
_oxdiff_exptl_absorpt_empirical_full_min 0.478
