# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_201811433
_database_code_depnum_ccdc_archive 'CCDC 1881743'
loop_
_audit_author_name
_audit_author_address
'xinjie Wu'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2018-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 O2'
_chemical_formula_sum            'C24 H16 O2'
_chemical_formula_weight         336.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.831(4)
_cell_length_b                   11.1480(6)
_cell_length_c                   14.9443(19)
_cell_angle_alpha                90
_cell_angle_beta                 133.61(2)
_cell_angle_gamma                90
_cell_volume                     3598.1(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1924
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9070
_cell_measurement_theta_min      4.0670
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6687
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         4.094
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -107.0000 -108.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   59.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega   72.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   49.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 12 omega   94.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
 13 omega   69.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   63.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   56.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 18 omega   81.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 19 omega   47.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0358073000
_diffrn_orient_matrix_UB_12      0.0608466000
_diffrn_orient_matrix_UB_13      -0.0274005000
_diffrn_orient_matrix_UB_21      -0.0592235000
_diffrn_orient_matrix_UB_22      0.0004988000
_diffrn_orient_matrix_UB_23      -0.1390751000
_diffrn_orient_matrix_UB_31      -0.0173192000
_diffrn_orient_matrix_UB_32      0.1240686000
_diffrn_orient_matrix_UB_33      0.0139756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2344
_reflns_number_total             3221
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00092(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.036
_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)+(0.0782P)²+0.5052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1501
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.36373(9) 0.32527(18) 0.26154(16) 0.0580(5) Uani 1 1 d . . . . .
C2 C 0.29748(8) 0.35283(16) 0.17830(15) 0.0525(4) Uani 1 1 d . . . . .
C3 C 0.27730(8) 0.46827(16) 0.15703(15) 0.0512(4) Uani 1 1 d . . . . .
C4 C 0.32163(8) 0.56454(17) 0.21859(15) 0.0540(5) Uani 1 1 d . . . . .
C5 C 0.38443(8) 0.53683(17) 0.29881(16) 0.0547(5) Uani 1 1 d . . . . .
C6 C 0.42979(8) 0.6235(2) 0.36296(17) 0.0637(5) Uani 1 1 d . . . . .
H6 H 0.4712 0.6012 0.4160 0.076 Uiso 1 1 calc R . . . .
C7 C 0.41438(9) 0.7430(2) 0.34934(19) 0.0690(6) Uani 1 1 d . . . . .
C8 C 0.35174(10) 0.77322(19) 0.2673(2) 0.0754(6) Uani 1 1 d . . . . .
H8 H 0.3404 0.8535 0.2556 0.091 Uiso 1 1 calc R . . . .
C9 C 0.30681(9) 0.68711(18) 0.20402(19) 0.0685(6) Uani 1 1 d . . . . .
H9 H 0.2655 0.7100 0.1500 0.082 Uiso 1 1 calc R . . . .
C10 C 0.25672(8) 0.25261(17) 0.12510(16) 0.0549(4) Uani 1 1 d . . . . .
C11 C 0.21992(9) 0.17234(18) 0.07889(17) 0.0581(5) Uani 1 1 d . . . . .
C12 C 0.17358(9) 0.08102(19) 0.02227(16) 0.0598(5) Uani 1 1 d . . . . .
C13 C 0.18749(11) -0.0384(2) 0.0278(2) 0.0775(6) Uani 1 1 d . . . . .
H13 H 0.2276 -0.0606 0.0675 0.093 Uiso 1 1 calc R . . . .
C14 C 0.14231(13) -0.1249(2) -0.0252(2) 0.0947(8) Uani 1 1 d . . . . .
H14 H 0.1521 -0.2052 -0.0210 0.114 Uiso 1 1 calc R . . . .
C15 C 0.08335(13) -0.0933(3) -0.0837(2) 0.0961(9) Uani 1 1 d . . . . .
H15 H 0.0531 -0.1520 -0.1188 0.115 Uiso 1 1 calc R . . . .
C16 C 0.06884(11) 0.0243(3) -0.0905(2) 0.0944(8) Uani 1 1 d . . . . .
H16 H 0.0286 0.0454 -0.1306 0.113 Uiso 1 1 calc R . . . .
C17 C 0.11304(10) 0.1122(2) -0.0390(2) 0.0774(6) Uani 1 1 d . . . . .
H17 H 0.1025 0.1923 -0.0449 0.093 Uiso 1 1 calc R . . . .
C18 C 0.20950(8) 0.49243(16) 0.07158(16) 0.0520(4) Uani 1 1 d . . . . .
C19 C 0.16931(8) 0.45522(18) -0.05049(17) 0.0624(5) Uani 1 1 d . . . . .
H19 H 0.1849 0.4193 -0.0805 0.075 Uiso 1 1 calc R . . . .
C20 C 0.10643(9) 0.4711(2) -0.12765(18) 0.0751(6) Uani 1 1 d . . . . .
H20 H 0.0797 0.4456 -0.2094 0.090 Uiso 1 1 calc R . . . .
C21 C 0.08317(9) 0.5244(2) -0.0839(2) 0.0791(7) Uani 1 1 d . . . . .
H21 H 0.0407 0.5350 -0.1362 0.095 Uiso 1 1 calc R . . . .
C22 C 0.12252(9) 0.5620(2) 0.0368(2) 0.0713(6) Uani 1 1 d . . . . .
H22 H 0.1066 0.5978 0.0662 0.086 Uiso 1 1 calc R . . . .
C23 C 0.18548(9) 0.54657(17) 0.11431(18) 0.0610(5) Uani 1 1 d . . . . .
H23 H 0.2120 0.5727 0.1958 0.073 Uiso 1 1 calc R . . . .
C24 C 0.46353(10) 0.8383(2) 0.4211(2) 0.0969(8) Uani 1 1 d . . . . .
H24A H 0.4992 0.8075 0.5009 0.145 Uiso 1 1 calc GR . . . .
H24B H 0.4479 0.9068 0.4313 0.145 Uiso 1 1 calc GR . . . .
H24C H 0.4749 0.8616 0.3771 0.145 Uiso 1 1 calc GR . . . .
O1 O 0.40407(6) 0.41977(12) 0.31829(12) 0.0624(4) Uani 1 1 d . . . . .
O2 O 0.38553(6) 0.22626(13) 0.28435(13) 0.0745(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
C1 C2 1.468(3) . ?
C1 O1 1.367(2) . ?
C1 O2 1.205(2) . ?
C2 C3 1.362(2) . ?
C2 C10 1.423(3) . ?
C3 C4 1.438(2) . ?
C3 C18 1.493(2) . ?
C4 C5 1.394(2) . ?
C4 C9 1.406(3) . ?
C5 C6 1.376(3) . ?
C5 O1 1.377(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C7 C8 1.396(3) . ?
C7 C24 1.503(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.199(3) . ?
C11 C12 1.432(3) . ?
C12 C13 1.380(3) . ?
C12 C17 1.393(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.362(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(2) . ?
C18 C23 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(3) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 C1 C2 117.30(16) . . ?
O2 C1 C2 125.43(18) . . ?
O2 C1 O1 117.26(17) . . ?
C3 C2 C1 121.02(17) . . ?
C3 C2 C10 122.79(16) . . ?
C10 C2 C1 116.17(16) . . ?
C2 C3 C4 119.49(16) . . ?
C2 C3 C18 119.32(16) . . ?
C4 C3 C18 121.18(16) . . ?
C5 C4 C3 118.82(17) . . ?
C5 C4 C9 116.17(17) . . ?
C9 C4 C3 125.01(16) . . ?
C6 C5 C4 122.40(19) . . ?
C6 C5 O1 116.59(16) . . ?
O1 C5 C4 121.01(17) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.57(17) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 118.09(19) . . ?
C6 C7 C24 121.09(19) . . ?
C8 C7 C24 120.8(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.49(18) . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C2 176.3(2) . . ?
C10 C11 C12 176.9(2) . . ?
C13 C12 C11 121.51(19) . . ?
C13 C12 C17 118.7(2) . . ?
C17 C12 C11 119.8(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 H17 120.1 . . ?
C16 C17 C12 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C3 120.22(17) . . ?
C23 C18 C3 120.71(16) . . ?
C23 C18 C19 118.99(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.39(19) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.14(19) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(2) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.36(18) . . ?
C22 C23 H23 119.8 . . ?
C7 C24 H24A 109.5 . . ?
C7 C24 H24B 109.5 . . ?
C7 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 O1 C5 122.35(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
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C18 179.92(16) . . . . ?
C2 C1 O1 C5 -0.5(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C9 179.59(18) . . . . ?
C2 C3 C18 C19 -59.7(2) . . . . ?
C2 C3 C18 C23 117.0(2) . . . . ?
C3 C4 C5 C6 -178.76(17) . . . . ?
C3 C4 C5 O1 0.7(3) . . . . ?
C3 C4 C9 C8 178.99(19) . . . . ?
C3 C18 C19 C20 176.20(19) . . . . ?
C3 C18 C23 C22 -176.05(19) . . . . ?
C4 C3 C18 C19 121.3(2) . . . . ?
C4 C3 C18 C23 -62.1(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C4 C5 O1 C1 -0.4(3) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C5 C6 C7 C24 178.5(2) . . . . ?
C6 C5 O1 C1 179.07(16) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C9 C4 C5 C6 1.6(3) . . . . ?
C9 C4 C5 O1 -178.89(16) . . . . ?
C10 C2 C3 C4 177.23(16) . . . . ?
C10 C2 C3 C18 -1.8(3) . . . . ?
C11 C12 C13 C14 178.6(2) . . . . ?
C11 C12 C17 C16 -178.3(2) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C18 C3 C4 C5 179.07(16) . . . . ?
C18 C3 C4 C9 -1.4(3) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C18 C23 C22 0.7(3) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C18 -0.5(3) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
C24 C7 C8 C9 -178.3(2) . . . . ?
O1 C1 C2 C3 1.3(3) . . . . ?
O1 C1 C2 C10 -177.07(15) . . . . ?
O1 C5 C6 C7 -179.88(17) . . . . ?
O2 C1 C2 C3 -179.00(18) . . . . ?
O2 C1 C2 C10 2.7(3) . . . . ?
O2 C1 O1 C5 179.72(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201911289
_database_code_depnum_ccdc_archive 'CCDC 1966838'
loop_
_audit_author_name
_audit_author_address
'xinjie Wu'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 O3'
_chemical_formula_sum            'C25 H18 O3'
_chemical_formula_weight         366.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4
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+1/2'
'x+1/2, -y, z'

_cell_length_a                   21.9993(4)
_cell_length_b                   12.5762(3)
_cell_length_c                   13.8028(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3818.78(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7370
_cell_measurement_theta_min      5.1140
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15382
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.019
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  36.00   0.50    2.50    --  -33.50  77.00   0.00   92
  2  ω    -84.00 -40.00   0.50    2.50    --  -33.50 -77.00-120.00   88
  3  ω    -61.00  -9.00   0.50    2.50    --  -33.50  77.00-120.00  104
  4  ω      6.00  31.00   0.50    2.50    --  -33.50  77.00-120.00   50
  5  ω    -72.00 -34.00   0.50    2.50    --  -33.50 178.00 -30.00   76
  6  ω    -30.00  -5.00   0.50    2.50    --  -33.50 -77.00-120.00   50
  7  ω     65.00  92.00   0.50    2.50    --   36.47  57.00 -30.00   54
  8  ω     20.00  60.00   0.50    2.50    --   36.47  57.00 -30.00   80
  9  ω     95.00 173.00   0.50   11.50    --  108.00  61.00   0.00  156
 10  ω    102.00 128.00   0.50   11.50    --  108.00 113.00 -46.00   52
 11  ω     79.00 109.00   0.50   11.50    --  108.00 -94.00 -90.00   60
 12  ω    153.00 178.00   0.50   11.50    --  108.00 113.00 -46.00   50
 13  ω    100.00 178.00   0.50   11.50    --  108.00 111.00  60.00  156
 14  ω    112.00 170.00   0.50   11.50    --  108.00  61.00-150.00  116
 15  ω     72.00 110.00   0.50   11.50    --  108.00 -45.00-120.00   76
 16  ω    -90.00 -65.00   0.50    2.00    --  -33.50 -57.00-150.00   50
 17  ω      8.00  44.00   0.50    2.00    --   36.47  77.00  60.00   72
 18  ω     72.00 110.00   0.50    2.00    --   36.47 178.00-120.00   76
 19  ω     68.00  96.00   0.50    2.00    --   36.47  77.00  60.00   56
 20  ω     43.00  69.00   0.50    2.00    --   36.47  57.00   0.00   52
 21  ω     75.00 101.00   0.50    2.00    --   36.47  57.00   0.00   52
 22  ω     37.00 105.00   0.50    6.00    --  108.00-111.00-120.00  136
 23  ω     40.00  66.00   0.50    6.00    --  108.00-111.00-150.00   52
 24  ω     46.00 121.00   0.50    6.00    --  108.00 -45.00  30.00  150
 25  ω     43.00  68.00   0.50    6.00    --  108.00 -94.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0044542000
_diffrn_orient_matrix_UB_12      0.0037853000
_diffrn_orient_matrix_UB_13      -0.1113486000
_diffrn_orient_matrix_UB_21      -0.0120995000
_diffrn_orient_matrix_UB_22      0.1206196000
_diffrn_orient_matrix_UB_23      0.0021626000
_diffrn_orient_matrix_UB_31      0.0688311000
_diffrn_orient_matrix_UB_32      0.0209466000
_diffrn_orient_matrix_UB_33      0.0075497000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5145
_reflns_number_total             6179
_reflns_odcompleteness_completeness 99.87
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         6179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.022
_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)+(0.0631P)²+0.1652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(3)
 0.2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C22(H22), C23(H23), C6'(H6'), C8'(H8'), C9'(H9'),
 C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C19'(H19'),
 C20'(H20'), C22'(H22'), C23'(H23')
3.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C24'(H24D,H24E,H24F), C25'(H25D,
 H25E,H25F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55221(15) 0.5743(3) 0.6940(3) 0.0640(8) Uani 1 1 d . . . . .
C2 C 0.51028(13) 0.4850(3) 0.7063(2) 0.0559(7) Uani 1 1 d . . . . .
C3 C 0.44865(13) 0.5000(2) 0.7135(2) 0.0521(6) Uani 1 1 d . . . . .
C4 C 0.42521(13) 0.6079(2) 0.7134(2) 0.0520(6) Uani 1 1 d . . . . .
C5 C 0.46541(14) 0.6910(3) 0.7006(3) 0.0580(7) Uani 1 1 d . . . . .
C6 C 0.44706(16) 0.7970(3) 0.7000(3) 0.0648(8) Uani 1 1 d . . . . .
H6 H 0.4755 0.8506 0.6901 0.078 Uiso 1 1 calc R . . . .
C7 C 0.38675(16) 0.8225(3) 0.7140(3) 0.0631(8) Uani 1 1 d . . . . .
C8 C 0.34592(15) 0.7401(3) 0.7289(3) 0.0649(8) Uani 1 1 d . . . . .
H8 H 0.3052 0.7560 0.7394 0.078 Uiso 1 1 calc R . . . .
C9 C 0.36417(14) 0.6353(3) 0.7285(3) 0.0600(8) Uani 1 1 d . . . . .
H9 H 0.3356 0.5819 0.7384 0.072 Uiso 1 1 calc R . . . .
C10 C 0.40687(13) 0.4081(2) 0.7187(3) 0.0555(7) Uani 1 1 d . . . . .
C11 C 0.36044(16) 0.3968(3) 0.6515(3) 0.0657(8) Uani 1 1 d . . . . .
H11 H 0.3544 0.4488 0.6046 0.079 Uiso 1 1 calc R . . . .
C12 C 0.32328(19) 0.3091(3) 0.6541(3) 0.0789(11) Uani 1 1 d . . . . .
H12 H 0.2923 0.3020 0.6087 0.095 Uiso 1 1 calc R . . . .
C13 C 0.33145(19) 0.2316(3) 0.7232(4) 0.0859(12) Uani 1 1 d . . . . .
H13 H 0.3063 0.1721 0.7242 0.103 Uiso 1 1 calc R . . . .
C14 C 0.37709(19) 0.2426(3) 0.7907(4) 0.0836(11) Uani 1 1 d . . . . .
H14 H 0.3828 0.1904 0.8375 0.100 Uiso 1 1 calc R . . . .
C15 C 0.41430(16) 0.3304(3) 0.7895(3) 0.0661(8) Uani 1 1 d . . . . .
H15 H 0.4445 0.3379 0.8361 0.079 Uiso 1 1 calc R . . . .
C16 C 0.53839(14) 0.3834(3) 0.7076(3) 0.0596(7) Uani 1 1 d . . . . .
C17 C 0.56363(14) 0.2992(3) 0.7080(3) 0.0614(8) Uani 1 1 d . . . . .
C18 C 0.59317(13) 0.1978(2) 0.7073(3) 0.0564(7) Uani 1 1 d . . . . .
C19 C 0.56157(14) 0.1050(3) 0.7219(3) 0.0730(10) Uani 1 1 d . . . . .
H19 H 0.5200 0.1078 0.7337 0.088 Uiso 1 1 calc R . . . .
C20 C 0.59071(16) 0.0071(3) 0.7194(4) 0.0800(11) Uani 1 1 d . . . . .
H20 H 0.5686 -0.0551 0.7289 0.096 Uiso 1 1 calc R . . . .
C21 C 0.65203(15) 0.0020(3) 0.7029(3) 0.0671(8) Uani 1 1 d . . . . .
C22 C 0.68411(15) 0.0944(3) 0.6892(3) 0.0719(10) Uani 1 1 d . . . . .
H22 H 0.7257 0.0912 0.6780 0.086 Uiso 1 1 calc R . . . .
C23 C 0.65574(15) 0.1906(3) 0.6919(3) 0.0672(9) Uani 1 1 d . . . . .
H23 H 0.6784 0.2524 0.6834 0.081 Uiso 1 1 calc R . . . .
C24 C 0.36659(19) 0.9370(3) 0.7158(4) 0.0797(10) Uani 1 1 d . . . . .
H24A H 0.3333 0.9465 0.6718 0.120 Uiso 1 1 calc GR . . . .
H24B H 0.3998 0.9819 0.6967 0.120 Uiso 1 1 calc GR . . . .
H24C H 0.3539 0.9556 0.7802 0.120 Uiso 1 1 calc GR . . . .
C25 C 0.6525(2) -0.1876(3) 0.7036(6) 0.126(2) Uani 1 1 d . . . . .
H25A H 0.6205 -0.1868 0.6563 0.188 Uiso 1 1 calc GR . . . .
H25B H 0.6354 -0.1963 0.7671 0.188 Uiso 1 1 calc GR . . . .
H25C H 0.6796 -0.2456 0.6902 0.188 Uiso 1 1 calc GR . . . .
O1 O 0.60597(11) 0.5687(2) 0.6856(3) 0.0871(9) Uani 1 1 d . . . . .
O2 O 0.52675(10) 0.67437(19) 0.6893(2) 0.0685(6) Uani 1 1 d . . . . .
O3 O 0.68518(13) -0.09012(19) 0.6994(3) 0.0948(10) Uani 1 1 d . . . . .
C1' C 0.44686(14) 0.7856(3) 0.4622(3) 0.0608(8) Uani 1 1 d . . . . .
C2' C 0.40647(14) 0.6936(3) 0.4560(2) 0.0543(7) Uani 1 1 d . . . . .
C3' C 0.34448(13) 0.7060(3) 0.4524(2) 0.0536(7) Uani 1 1 d . . . . .
C4' C 0.31943(13) 0.8127(2) 0.4531(2) 0.0544(7) Uani 1 1 d . . . . .
C5' C 0.35815(13) 0.8979(3) 0.4592(3) 0.0582(7) Uani 1 1 d . . . . .
C6' C 0.33775(17) 1.0025(3) 0.4596(3) 0.0691(9) Uani 1 1 d . . . . .
H6' H 0.3654 1.0582 0.4641 0.083 Uiso 1 1 calc R . . . .
C7' C 0.27629(17) 1.0233(3) 0.4534(3) 0.0711(9) Uani 1 1 d . . . . .
C8' C 0.23690(15) 0.9384(3) 0.4461(3) 0.0721(9) Uani 1 1 d . . . . .
H8' H 0.1954 0.9513 0.4420 0.087 Uiso 1 1 calc R . . . .
C9' C 0.25722(15) 0.8359(3) 0.4449(3) 0.0650(8) Uani 1 1 d . . . . .
H9' H 0.2294 0.7806 0.4384 0.078 Uiso 1 1 calc R . . . .
C10' C 0.30342(13) 0.6133(3) 0.4464(3) 0.0614(8) Uani 1 1 d . . . . .
C11' C 0.26012(15) 0.5947(3) 0.5180(3) 0.0722(10) Uani 1 1 d . . . . .
H11' H 0.2573 0.6406 0.5706 0.087 Uiso 1 1 calc R . . . .
C12' C 0.22146(19) 0.5088(4) 0.5116(4) 0.0947(15) Uani 1 1 d . . . . .
H12' H 0.1928 0.4966 0.5598 0.114 Uiso 1 1 calc R . . . .
C13' C 0.2254(2) 0.4409(4) 0.4330(6) 0.114(2) Uani 1 1 d . . . . .
H13' H 0.1993 0.3830 0.4284 0.137 Uiso 1 1 calc R . . . .
C14' C 0.2679(3) 0.4588(4) 0.3618(5) 0.1088(18) Uani 1 1 d . . . . .
H14' H 0.2702 0.4131 0.3090 0.131 Uiso 1 1 calc R . . . .
C15' C 0.30708(19) 0.5438(3) 0.3681(3) 0.0805(11) Uani 1 1 d . . . . .
H15' H 0.3360 0.5549 0.3200 0.097 Uiso 1 1 calc R . . . .
C16' C 0.43552(13) 0.5931(3) 0.4570(3) 0.0581(7) Uani 1 1 d . . . . .
C17' C 0.46165(13) 0.5094(3) 0.4567(3) 0.0581(7) Uani 1 1 d . . . . .
C18' C 0.49132(14) 0.4086(3) 0.4555(3) 0.0585(7) Uani 1 1 d . . . . .
C19' C 0.45862(15) 0.3150(3) 0.4503(3) 0.0710(9) Uani 1 1 d . . . . .
H19' H 0.4164 0.3178 0.4468 0.085 Uiso 1 1 calc R . . . .
C20' C 0.48739(17) 0.2167(3) 0.4501(3) 0.0751(10) Uani 1 1 d . . . . .
H20' H 0.4646 0.1546 0.4461 0.090 Uiso 1 1 calc R . . . .
C21' C 0.54995(15) 0.2116(3) 0.4559(3) 0.0591(7) Uani 1 1 d . . . . .
C22' C 0.58309(14) 0.3047(3) 0.4608(3) 0.0578(7) Uani 1 1 d . . . . .
H22' H 0.6253 0.3017 0.4638 0.069 Uiso 1 1 calc R . . . .
C23' C 0.55423(14) 0.4015(3) 0.4612(3) 0.0570(7) Uani 1 1 d . . . . .
H23' H 0.5772 0.4634 0.4654 0.068 Uiso 1 1 calc R . . . .
C24' C 0.2531(3) 1.1362(3) 0.4543(5) 0.0997(13) Uani 1 1 d . . . . .
H24D H 0.2435 1.1565 0.5196 0.150 Uiso 1 1 calc GR . . . .
H24E H 0.2172 1.1410 0.4150 0.150 Uiso 1 1 calc GR . . . .
H24F H 0.2837 1.1828 0.4290 0.150 Uiso 1 1 calc GR . . . .
C25' C 0.5505(2) 0.0225(3) 0.4576(4) 0.0929(12) Uani 1 1 d . . . . .
H25D H 0.5256 0.0176 0.4007 0.139 Uiso 1 1 calc GR . . . .
H25E H 0.5252 0.0193 0.5142 0.139 Uiso 1 1 calc GR . . . .
H25F H 0.5788 -0.0356 0.4586 0.139 Uiso 1 1 calc GR . . . .
O1' O 0.50135(11) 0.7825(2) 0.4639(2) 0.0798(7) Uani 1 1 d . . . . .
O2' O 0.42035(10) 0.88444(19) 0.4653(2) 0.0675(6) Uani 1 1 d . . . . .
O3' O 0.58278(11) 0.1199(2) 0.4567(2) 0.0757(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.463(5) . ?
C1 O1 1.190(4) . ?
C1 O2 1.379(4) . ?
C2 C3 1.373(4) . ?
C2 C16 1.419(4) . ?
C3 C4 1.452(4) . ?
C3 C10 1.478(4) . ?
C4 C5 1.380(4) . ?
C4 C9 1.402(4) . ?
C5 C6 1.392(4) . ?
C5 O2 1.374(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(5) . ?
C7 C8 1.387(5) . ?
C7 C24 1.507(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(5) . ?
C10 C15 1.391(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.196(4) . ?
C17 C18 1.431(4) . ?
C18 C19 1.373(5) . ?
C18 C23 1.396(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.369(5) . ?
C21 C22 1.373(5) . ?
C21 O3 1.370(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.362(5) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 O3 1.422(5) . ?
C1' C2' 1.461(5) . ?
C1' O1' 1.200(4) . ?
C1' O2' 1.374(4) . ?
C2' C3' 1.373(4) . ?
C2' C16' 1.417(4) . ?
C3' C4' 1.450(4) . ?
C3' C10' 1.477(4) . ?
C4' C5' 1.372(5) . ?
C4' C9' 1.404(4) . ?
C5' C6' 1.390(5) . ?
C5' O2' 1.381(4) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.380(5) . ?
C7' C8' 1.379(5) . ?
C7' C24' 1.508(5) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.365(5) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.392(6) . ?
C10' C15' 1.392(5) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.377(6) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.383(8) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.374(9) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.376(7) . ?
C15' H15' 0.9300 . ?
C16' C17' 1.198(4) . ?
C17' C18' 1.426(4) . ?
C18' C19' 1.382(5) . ?
C18' C23' 1.389(4) . ?
C19' H19' 0.9300 . ?
C19' C20' 1.388(5) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.380(5) . ?
C21' C22' 1.380(5) . ?
C21' O3' 1.361(4) . ?
C22' H22' 0.9300 . ?
C22' C23' 1.374(4) . ?
C23' H23' 0.9300 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 0.9600 . ?
C25' O3' 1.417(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 126.3(3) . . ?
O1 C1 O2 116.9(3) . . ?
O2 C1 C2 116.7(3) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 C16 123.6(3) . . ?
C16 C2 C1 114.7(3) . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 C10 120.7(3) . . ?
C4 C3 C10 120.7(2) . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 C9 116.5(3) . . ?
C9 C4 C3 124.7(3) . . ?
C4 C5 C6 122.7(3) . . ?
O2 C5 C4 121.9(3) . . ?
O2 C5 C6 115.5(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 118.1(3) . . ?
C6 C7 C24 120.5(3) . . ?
C8 C7 C24 121.4(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.1 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C3 120.4(3) . . ?
C11 C10 C15 118.9(3) . . ?
C15 C10 C3 120.7(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C2 178.1(4) . . ?
C16 C17 C18 179.2(4) . . ?
C19 C18 C17 121.8(3) . . ?
C19 C18 C23 117.8(3) . . ?
C23 C18 C17 120.4(3) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 119.3(3) . . ?
C20 C21 O3 124.7(3) . . ?
O3 C21 C22 115.9(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.9(3) . . ?
C22 C23 H23 119.6 . . ?
C7 C24 H24A 109.5 . . ?
C7 C24 H24B 109.5 . . ?
C7 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
C5 O2 C1 122.2(3) . . ?
C21 O3 C25 117.3(3) . . ?
O1' C1' C2' 125.7(3) . . ?
O1' C1' O2' 116.9(3) . . ?
O2' C1' C2' 117.4(3) . . ?
C3' C2' C1' 121.0(3) . . ?
C3' C2' C16' 123.3(3) . . ?
C16' C2' C1' 115.6(3) . . ?
C2' C3' C4' 118.8(3) . . ?
C2' C3' C10' 121.3(3) . . ?
C4' C3' C10' 119.9(3) . . ?
C5' C4' C3' 119.1(3) . . ?
C5' C4' C9' 116.6(3) . . ?
C9' C4' C3' 124.2(3) . . ?
C4' C5' C6' 122.6(3) . . ?
C4' C5' O2' 121.5(3) . . ?
O2' C5' C6' 115.8(3) . . ?
C5' C6' H6' 120.1 . . ?
C7' C6' C5' 119.7(3) . . ?
C7' C6' H6' 120.1 . . ?
C6' C7' C24' 120.7(4) . . ?
C8' C7' C6' 118.2(3) . . ?
C8' C7' C24' 121.1(4) . . ?
C7' C8' H8' 119.1 . . ?
C9' C8' C7' 121.8(3) . . ?
C9' C8' H8' 119.1 . . ?
C4' C9' H9' 119.5 . . ?
C8' C9' C4' 121.0(3) . . ?
C8' C9' H9' 119.5 . . ?
C11' C10' C3' 120.8(3) . . ?
C11' C10' C15' 119.0(4) . . ?
C15' C10' C3' 120.2(4) . . ?
C10' C11' H11' 119.7 . . ?
C12' C11' C10' 120.6(4) . . ?
C12' C11' H11' 119.7 . . ?
C11' C12' H12' 120.1 . . ?
C11' C12' C13' 119.7(5) . . ?
C13' C12' H12' 120.1 . . ?
C12' C13' H13' 119.9 . . ?
C14' C13' C12' 120.1(5) . . ?
C14' C13' H13' 119.9 . . ?
C13' C14' H14' 119.7 . . ?
C13' C14' C15' 120.6(5) . . ?
C15' C14' H14' 119.7 . . ?
C10' C15' H15' 120.0 . . ?
C14' C15' C10' 120.0(5) . . ?
C14' C15' H15' 120.0 . . ?
C17' C16' C2' 178.0(3) . . ?
C16' C17' C18' 178.5(4) . . ?
C19' C18' C17' 121.3(3) . . ?
C19' C18' C23' 117.8(3) . . ?
C23' C18' C17' 120.8(3) . . ?
C18' C19' H19' 119.3 . . ?
C18' C19' C20' 121.4(3) . . ?
C20' C19' H19' 119.3 . . ?
C19' C20' H20' 120.1 . . ?
C21' C20' C19' 119.7(3) . . ?
C21' C20' H20' 120.1 . . ?
C20' C21' C22' 119.4(3) . . ?
O3' C21' C20' 124.7(3) . . ?
O3' C21' C22' 115.9(3) . . ?
C21' C22' H22' 119.7 . . ?
C23' C22' C21' 120.5(3) . . ?
C23' C22' H22' 119.7 . . ?
C18' C23' H23' 119.4 . . ?
C22' C23' C18' 121.1(3) . . ?
C22' C23' H23' 119.4 . . ?
C7' C24' H24D 109.5 . . ?
C7' C24' H24E 109.5 . . ?
C7' C24' H24F 109.5 . . ?
H24D C24' H24E 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
H25D C25' H25E 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
O3' C25' H25D 109.5 . . ?
O3' C25' H25E 109.5 . . ?
O3' C25' H25F 109.5 . . ?
C1' O2' C5' 122.0(3) . . ?
C21' O3' C25' 117.8(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 -3.0(5) . . . . ?
C1 C2 C3 C10 175.5(3) . . . . ?
C2 C1 O2 C5 3.3(5) . . . . ?
C2 C3 C4 C5 3.6(5) . . . . ?
C2 C3 C4 C9 -174.2(3) . . . . ?
C2 C3 C10 C11 -123.3(4) . . . . ?
C2 C3 C10 C15 55.2(5) . . . . ?
C3 C4 C5 C6 -179.7(3) . . . . ?
C3 C4 C5 O2 -0.8(5) . . . . ?
C3 C4 C9 C8 178.9(3) . . . . ?
C3 C10 C11 C12 177.3(3) . . . . ?
C3 C10 C15 C14 -176.8(3) . . . . ?
C4 C3 C10 C11 55.1(4) . . . . ?
C4 C3 C10 C15 -126.4(3) . . . . ?
C4 C5 C6 C7 1.1(6) . . . . ?
C4 C5 O2 C1 -2.7(5) . . . . ?
C5 C4 C9 C8 1.0(5) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
C5 C6 C7 C24 178.5(4) . . . . ?
C6 C5 O2 C1 176.2(3) . . . . ?
C6 C7 C8 C9 -0.9(6) . . . . ?
C7 C8 C9 C4 0.3(6) . . . . ?
C9 C4 C5 C6 -1.7(5) . . . . ?
C9 C4 C5 O2 177.2(3) . . . . ?
C10 C3 C4 C5 -174.9(3) . . . . ?
C10 C3 C4 C9 7.3(5) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C11 C10 C15 C14 1.8(5) . . . . ?
C11 C12 C13 C14 0.5(7) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C13 C14 C15 C10 -1.2(6) . . . . ?
C15 C10 C11 C12 -1.3(5) . . . . ?
C16 C2 C3 C4 178.7(3) . . . . ?
C16 C2 C3 C10 -2.8(5) . . . . ?
C17 C18 C19 C20 178.9(4) . . . . ?
C17 C18 C23 C22 -178.7(4) . . . . ?
C18 C19 C20 C21 0.5(7) . . . . ?
C19 C18 C23 C22 1.5(6) . . . . ?
C19 C20 C21 C22 0.1(7) . . . . ?
C19 C20 C21 O3 179.7(4) . . . . ?
C20 C21 C22 C23 0.1(7) . . . . ?
C20 C21 O3 C25 6.6(8) . . . . ?
C21 C22 C23 C18 -0.9(7) . . . . ?
C22 C21 O3 C25 -173.9(5) . . . . ?
C23 C18 C19 C20 -1.3(6) . . . . ?
C24 C7 C8 C9 -179.2(4) . . . . ?
O1 C1 C2 C3 -178.7(4) . . . . ?
O1 C1 C2 C16 -0.2(6) . . . . ?
O1 C1 O2 C5 -178.2(3) . . . . ?
O2 C1 C2 C3 -0.4(5) . . . . ?
O2 C1 C2 C16 178.1(3) . . . . ?
O2 C5 C6 C7 -177.8(3) . . . . ?
O3 C21 C22 C23 -179.5(4) . . . . ?
C1' C2' C3' C4' 1.0(5) . . . . ?
C1' C2' C3' C10' -179.8(3) . . . . ?
C2' C1' O2' C5' -2.4(5) . . . . ?
C2' C3' C4' C5' -1.2(5) . . . . ?
C2' C3' C4' C9' 176.7(3) . . . . ?
C2' C3' C10' C11' 120.1(4) . . . . ?
C2' C3' C10' C15' -60.7(5) . . . . ?
C3' C4' C5' C6' 179.5(3) . . . . ?
C3' C4' C5' O2' -0.5(6) . . . . ?
C3' C4' C9' C8' -180.0(4) . . . . ?
C3' C10' C11' C12' 179.2(3) . . . . ?
C3' C10' C15' C14' -178.6(4) . . . . ?
C4' C3' C10' C11' -60.7(5) . . . . ?
C4' C3' C10' C15' 118.5(4) . . . . ?
C4' C5' C6' C7' -0.3(6) . . . . ?
C4' C5' O2' C1' 2.3(6) . . . . ?
C5' C4' C9' C8' -2.1(6) . . . . ?
C5' C6' C7' C8' -0.5(6) . . . . ?
C5' C6' C7' C24' 179.6(4) . . . . ?
C6' C5' O2' C1' -177.7(3) . . . . ?
C6' C7' C8' C9' -0.1(7) . . . . ?
C7' C8' C9' C4' 1.4(7) . . . . ?
C9' C4' C5' C6' 1.5(6) . . . . ?
C9' C4' C5' O2' -178.5(3) . . . . ?
C10' C3' C4' C5' 179.6(3) . . . . ?
C10' C3' C4' C9' -2.5(6) . . . . ?
C10' C11' C12' C13' -0.4(6) . . . . ?
C11' C10' C15' C14' 0.5(6) . . . . ?
C11' C12' C13' C14' 0.2(7) . . . . ?
C12' C13' C14' C15' 0.4(8) . . . . ?
C13' C14' C15' C10' -0.8(7) . . . . ?
C15' C10' C11' C12' 0.0(5) . . . . ?
C16' C2' C3' C4' 179.1(3) . . . . ?
C16' C2' C3' C10' -1.7(6) . . . . ?
C17' C18' C19' C20' -179.3(4) . . . . ?
C17' C18' C23' C22' 179.5(3) . . . . ?
C18' C19' C20' C21' 0.5(7) . . . . ?
C19' C18' C23' C22' 0.6(6) . . . . ?
C19' C20' C21' C22' -0.7(7) . . . . ?
C19' C20' C21' O3' 179.8(4) . . . . ?
C20' C21' C22' C23' 0.9(6) . . . . ?
C20' C21' O3' C25' -4.1(7) . . . . ?
C21' C22' C23' C18' -0.8(6) . . . . ?
C22' C21' O3' C25' 176.3(4) . . . . ?
C23' C18' C19' C20' -0.4(7) . . . . ?
C24' C7' C8' C9' 179.8(5) . . . . ?
O1' C1' C2' C3' -178.6(4) . . . . ?
O1' C1' C2' C16' 3.2(6) . . . . ?
O1' C1' O2' C5' 177.0(4) . . . . ?
O2' C1' C2' C3' 0.7(5) . . . . ?
O2' C1' C2' C16' -177.5(3) . . . . ?
O2' C5' C6' C7' 179.7(4) . . . . ?
O3' C21' C22' C23' -179.5(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 2.555
_oxdiff_exptl_absorpt_empirical_full_min 0.814
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(3)
2 0.2(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_201911285
_database_code_depnum_ccdc_archive 'CCDC 1966837'
loop_
_audit_author_name
_audit_author_address
'xinjie Wu'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H13 F3 O2'
_chemical_formula_sum            'C24 H13 F3 O2'
_chemical_formula_weight         390.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4F3
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'
F F 0.0727 0.0534 '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                   11.8769(8)
_cell_length_b                   11.8650(6)
_cell_length_c                   14.2912(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.026(8)
_cell_angle_gamma                90
_cell_volume                     1892.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1789
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6380
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_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  0.0234
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.962
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  -5.00   1.00    2.50    --  -33.50 -77.00 -30.00   80
  2  ω    -41.00 -15.00   1.00    2.50    --  -33.50 -57.00-180.00   26
  3  ω    -88.00 -43.00   1.00    2.50    --  -33.50 -57.00 120.00   45
  4  ω    -93.00 -60.00   1.00    2.50    --  -33.50 -57.00-180.00   33
  5  ω     62.00  87.00   1.00    2.50    --   36.47 178.00-120.00   25
  6  ω     77.00 102.00   1.00    2.50    --   36.47 178.00 -60.00   25
  7  ω     58.00 109.00   1.00    2.50    --   36.47 178.00-180.00   51
  8  ω     58.00 102.00   1.00    2.50    --   36.47 178.00  90.00   44
  9  ω    -27.00  46.00   1.00    2.50    --   36.47 -57.00-120.00   73
 10  ω     88.00 172.00   1.00   10.00    --  108.00  45.00 150.00   84
 11  ω    112.00 141.00   1.00   10.00    --  108.00  77.00-120.00   29
 12  ω     43.00  70.00   1.00   10.00    --  108.00 -77.00   0.00   27
 13  ω     42.00 120.00   1.00   10.00    --  108.00 -45.00   0.00   78
 14  ω     84.00 134.00   1.00   10.00    --  108.00 -30.00 120.00   50
 15  ω     37.00  63.00   1.00   10.00    --  108.00 -30.00 120.00   26
 16  ω     50.00 109.00   1.00   10.00    --  108.00 -94.00-180.00   59
 17  ω     71.00 109.00   1.00   10.00    --  108.00 -77.00   0.00   38
 18  ω     43.00  96.00   1.00   10.00    --  108.00 -94.00 -30.00   53
 19  ω    110.00 143.00   1.00   10.00    --  108.00 178.00  30.00   33
 20  ω     60.00  98.00   1.00   10.00    --  108.00 178.00  30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1280686000
_diffrn_orient_matrix_UB_12      0.0430326000
_diffrn_orient_matrix_UB_13      -0.0175468000
_diffrn_orient_matrix_UB_21      0.0011211000
_diffrn_orient_matrix_UB_22      0.0633881000
_diffrn_orient_matrix_UB_23      -0.0937611000
_diffrn_orient_matrix_UB_31      -0.0514381000
_diffrn_orient_matrix_UB_32      -0.1048471000
_diffrn_orient_matrix_UB_33      -0.0637929000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2485
_reflns_number_total             3371
_reflns_odcompleteness_completeness 99.86
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.133
_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)+(0.0872P)²+0.6254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1862
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F3A-C24
 1.35 with sigma of 0.02
 F3-F1 \\sim F3-F2 \\sim F1-F2 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.04
 C24-F3 \\sim C24-F1 \\sim C24-F2 \\sim C24-F1A \\sim C24-F2A \\sim C24-F3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.1905(2) 0.5633(2) 0.69528(19) 0.0565(6) Uani 1 1 d . . . . .
C2 C 0.0644(2) 0.5974(2) 0.64710(18) 0.0523(6) Uani 1 1 d . . . . .
C3 C 0.0325(2) 0.7083(2) 0.63362(18) 0.0510(6) Uani 1 1 d . . . . .
C4 C 0.1248(2) 0.7932(2) 0.66818(18) 0.0518(6) Uani 1 1 d . . . . .
C5 C 0.2428(2) 0.7585(2) 0.71648(18) 0.0539(6) Uani 1 1 d . . . . .
C6 C 0.3353(3) 0.8337(2) 0.7547(2) 0.0647(7) Uani 1 1 d . . . . .
H6 H 0.4129 0.8080 0.7873 0.078 Uiso 1 1 calc R . . . .
C7 C 0.3117(3) 0.9470(3) 0.7444(2) 0.0694(8) Uani 1 1 d . . . . .
C8 C 0.1964(3) 0.9855(2) 0.6937(3) 0.0734(8) Uani 1 1 d . . . . .
H8 H 0.1813 1.0624 0.6852 0.088 Uiso 1 1 calc R . . . .
C9 C 0.1048(3) 0.9094(2) 0.6563(2) 0.0634(7) Uani 1 1 d . . . . .
H9 H 0.0278 0.9356 0.6224 0.076 Uiso 1 1 calc R . . . .
C10 C -0.0954(2) 0.7404(2) 0.58343(19) 0.0531(6) Uani 1 1 d . . . . .
C11 C -0.1564(2) 0.8033(2) 0.6328(2) 0.0615(7) Uani 1 1 d . . . . .
H11 H -0.1167 0.8280 0.6975 0.074 Uiso 1 1 calc R . . . .
C12 C -0.2763(3) 0.8292(3) 0.5857(3) 0.0717(8) Uani 1 1 d . . . . .
H12 H -0.3174 0.8700 0.6194 0.086 Uiso 1 1 calc R . . . .
C13 C -0.3344(3) 0.7951(3) 0.4901(3) 0.0765(9) Uani 1 1 d . . . . .
H13 H -0.4144 0.8143 0.4584 0.092 Uiso 1 1 calc R . . . .
C14 C -0.2750(3) 0.7322(3) 0.4402(2) 0.0743(8) Uani 1 1 d . . . . .
H14 H -0.3151 0.7088 0.3751 0.089 Uiso 1 1 calc R . . . .
C15 C -0.1564(2) 0.7042(2) 0.4868(2) 0.0626(7) Uani 1 1 d . . . . .
H15 H -0.1169 0.6608 0.4535 0.075 Uiso 1 1 calc R . . . .
C16 C -0.0180(2) 0.5064(2) 0.61877(19) 0.0562(6) Uani 1 1 d . . . . .
C17 C -0.0838(2) 0.4265(2) 0.59610(19) 0.0561(6) Uani 1 1 d . . . . .
C18 C -0.1623(2) 0.3321(2) 0.56606(18) 0.0539(6) Uani 1 1 d . . . . .
C19 C -0.2826(3) 0.3476(3) 0.5110(2) 0.0686(8) Uani 1 1 d . . . . .
H19 H -0.3126 0.4199 0.4936 0.082 Uiso 1 1 calc R . . . .
C20 C -0.3575(3) 0.2559(3) 0.4821(3) 0.0837(10) Uani 1 1 d . . . . .
H20 H -0.4380 0.2669 0.4450 0.100 Uiso 1 1 calc R . . . .
C21 C -0.3156(3) 0.1494(3) 0.5069(3) 0.0810(9) Uani 1 1 d . . . . .
H21 H -0.3672 0.0881 0.4871 0.097 Uiso 1 1 calc R . . . .
C22 C -0.1966(3) 0.1329(2) 0.5615(2) 0.0749(8) Uani 1 1 d . . . . .
H22 H -0.1677 0.0601 0.5785 0.090 Uiso 1 1 calc R . . . .
C23 C -0.1201(3) 0.2230(2) 0.5910(2) 0.0633(7) Uani 1 1 d . . . . .
H23 H -0.0397 0.2111 0.6278 0.076 Uiso 1 1 calc R . . . .
C24 C 0.4114(4) 1.0274(3) 0.7870(4) 0.1034(13) Uani 1 1 d D . . . .
F1 F 0.4724(4) 1.0393(5) 0.7213(4) 0.1514(17) Uani 0.686(4) 1 d D U P A 1
F1A F 0.4048(10) 1.0652(11) 0.8803(9) 0.1514(17) Uani 0.314(4) 1 d D U P A 2
F2 F 0.4927(5) 0.9947(6) 0.8693(4) 0.155(3) Uani 0.686(4) 1 d D U P A 1
F2A F 0.5169(11) 0.9888(14) 0.8177(10) 0.155(3) Uani 0.314(4) 1 d D U P A 2
F3 F 0.3777(5) 1.1345(3) 0.7896(4) 0.133(2) Uani 0.686(4) 1 d D U P A 1
F3A F 0.4104(13) 1.1178(8) 0.7450(9) 0.133(2) Uani 0.314(4) 1 d D U P A 2
O1 O 0.22547(19) 0.46797(16) 0.70794(16) 0.0750(6) Uani 1 1 d . . . . .
O2 O 0.27335(16) 0.64675(15) 0.72919(14) 0.0615(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
C1 C2 1.475(4) . ?
C1 O1 1.197(3) . ?
C1 O2 1.363(3) . ?
C2 C3 1.364(3) . ?
C2 C16 1.419(4) . ?
C3 C4 1.446(3) . ?
C3 C10 1.490(4) . ?
C4 C5 1.396(4) . ?
C4 C9 1.399(4) . ?
C5 C6 1.374(4) . ?
C5 O2 1.371(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(4) . ?
C7 C8 1.388(4) . ?
C7 C24 1.480(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(4) . ?
C10 C15 1.390(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.201(4) . ?
C17 C18 1.427(4) . ?
C18 C19 1.387(4) . ?
C18 C23 1.390(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.360(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(4) . ?
C23 H23 0.9300 . ?
C24 F1 1.375(6) . ?
C24 F1A 1.435(9) . ?
C24 F2 1.300(6) . ?
C24 F2A 1.263(12) . ?
C24 F3 1.337(6) . ?
C24 F3A 1.227(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 125.1(3) . . ?
O1 C1 O2 117.5(3) . . ?
O2 C1 C2 117.4(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 C16 124.2(2) . . ?
C16 C2 C1 114.5(2) . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 C10 120.2(2) . . ?
C4 C3 C10 120.9(2) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 C9 116.8(2) . . ?
C9 C4 C3 124.6(2) . . ?
C6 C5 C4 122.4(2) . . ?
O2 C5 C4 121.7(2) . . ?
O2 C5 C6 115.9(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 C24 118.8(3) . . ?
C8 C7 C24 120.7(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.4(3) . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C3 121.1(2) . . ?
C11 C10 C15 119.0(2) . . ?
C15 C10 C3 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C2 177.3(3) . . ?
C16 C17 C18 178.3(3) . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 C23 118.7(3) . . ?
C23 C18 C17 120.8(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
F1 C24 C7 108.6(4) . . ?
F1A C24 C7 107.0(5) . . ?
F2 C24 C7 115.0(4) . . ?
F2 C24 F1 104.3(5) . . ?
F2 C24 F3 113.3(5) . . ?
F2A C24 C7 117.9(8) . . ?
F2A C24 F1A 98.9(8) . . ?
F3 C24 C7 114.8(4) . . ?
F3 C24 F1 98.9(5) . . ?
F3A C24 C7 119.3(7) . . ?
F3A C24 F1A 100.8(7) . . ?
F3A C24 F2A 109.3(10) . . ?
C1 O2 C5 122.0(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
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C10 179.1(2) . . . . ?
C2 C1 O2 C5 -2.3(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 C9 178.0(2) . . . . ?
C2 C3 C10 C11 118.6(3) . . . . ?
C2 C3 C10 C15 -59.2(3) . . . . ?
C3 C4 C5 C6 -177.7(2) . . . . ?
C3 C4 C5 O2 1.9(4) . . . . ?
C3 C4 C9 C8 178.0(3) . . . . ?
C3 C10 C11 C12 -177.9(2) . . . . ?
C3 C10 C15 C14 179.2(3) . . . . ?
C4 C3 C10 C11 -61.9(3) . . . . ?
C4 C3 C10 C15 120.3(3) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C4 C5 O2 C1 0.2(4) . . . . ?
C5 C4 C9 C8 -2.3(4) . . . . ?
C5 C6 C7 C8 -1.5(5) . . . . ?
C5 C6 C7 C24 179.2(3) . . . . ?
C6 C5 O2 C1 179.7(2) . . . . ?
C6 C7 C8 C9 1.9(5) . . . . ?
C6 C7 C24 F1 82.0(5) . . . . ?
C6 C7 C24 F1A -99.5(7) . . . . ?
C6 C7 C24 F2 -34.4(7) . . . . ?
C6 C7 C24 F2A 10.6(10) . . . . ?
C6 C7 C24 F3 -168.4(5) . . . . ?
C6 C7 C24 F3A 147.1(9) . . . . ?
C7 C8 C9 C4 0.1(5) . . . . ?
C8 C7 C24 F1 -97.3(5) . . . . ?
C8 C7 C24 F1A 81.2(8) . . . . ?
C8 C7 C24 F2 146.3(5) . . . . ?
C8 C7 C24 F2A -168.7(9) . . . . ?
C8 C7 C24 F3 12.3(7) . . . . ?
C8 C7 C24 F3A -32.2(10) . . . . ?
C9 C4 C5 C6 2.7(4) . . . . ?
C9 C4 C5 O2 -177.8(2) . . . . ?
C10 C3 C4 C5 178.8(2) . . . . ?
C10 C3 C4 C9 -1.6(4) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C11 C10 C15 C14 1.3(4) . . . . ?
C11 C12 C13 C14 1.5(5) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C10 -1.1(5) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C16 C2 C3 C4 178.4(2) . . . . ?
C16 C2 C3 C10 -2.1(4) . . . . ?
C17 C18 C19 C20 179.8(3) . . . . ?
C17 C18 C23 C22 -179.9(3) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C18 C23 C22 -0.1(4) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C23 C18 C19 C20 0.0(4) . . . . ?
C24 C7 C8 C9 -178.8(4) . . . . ?
O1 C1 C2 C3 -178.5(3) . . . . ?
O1 C1 C2 C16 2.5(4) . . . . ?
O1 C1 O2 C5 178.6(2) . . . . ?
O2 C1 C2 C3 2.4(4) . . . . ?
O2 C1 C2 C16 -176.5(2) . . . . ?
O2 C5 C6 C7 179.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.827
####################################################################### 
# 
# 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_201911292
_database_code_depnum_ccdc_archive 'CCDC 1966843'
loop_
_audit_author_name
_audit_author_address
'xinjie Wu'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 F O3'
_chemical_formula_sum            'C24 H15 F O3'
_chemical_formula_weight         370.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4F1
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'
F F 0.0727 0.0534 '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+1/2'
'x+1/2, -y, z'

_cell_length_a                   21.9897(6)
_cell_length_b                   12.2777(3)
_cell_length_c                   13.5508(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3658.47(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3453
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.4180
_cell_measurement_theta_min      4.0300
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13127
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        67.337
_diffrn_reflns_theta_max         67.337
_diffrn_reflns_theta_min         3.600
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00 -49.00   1.00    1.50    --  -33.50 178.00-120.00   48
  2  ω   -101.00 -51.00   1.00    1.50    --  -33.50 -57.00 -90.00   50
  3  ω    -45.00 -17.00   1.00    1.50    --  -33.50 -57.00-150.00   28
  4  ω     71.00 110.00   1.00    1.50    --   36.47 178.00-150.00   39
  5  ω     41.00  68.00   1.00    1.50    --   36.47 -99.00 -90.00   27
  6  ω     60.00 109.00   1.00    1.50    --   36.47 178.00 -30.00   49
  7  ω     -4.00  22.00   1.00    1.50    --   36.47 -99.00 -90.00   26
  8  ω     59.00 106.00   1.00    5.00    --  108.00-111.00 -60.00   47
  9  ω    105.00 178.00   1.00    5.00    --  108.00 111.00-150.00   73
 10  ω     40.00  78.00   1.00    5.00    --  108.00 -94.00-180.00   38
 11  ω    100.00 178.00   1.00    5.00    --  108.00 111.00  90.00   78
 12  ω     47.00 131.00   1.00    5.00    --  108.00 -30.00 120.00   84
 13  ω   -102.00 -76.00   1.00    2.50    --  -33.50 178.00-180.00   26
 14  ω     47.00  72.00   1.00    2.50    --   36.47 -19.00  90.00   25
 15  ω     31.00  62.00   1.00    2.50    --   36.47 -99.00  60.00   31
 16  ω    -32.00  33.00   1.00    2.50    --   36.47 -19.00  90.00   65
 17  ω     45.00  88.00   1.00    2.50    --   36.47  56.00-117.00   43
 18  ω     32.00  58.00   1.00    2.50    --   36.47 -99.00 -30.00   26
 19  ω     59.00 105.00   1.00    3.00    --  108.00 -94.00 -30.00   46
 20  ω    111.00 148.00   1.00    3.00    --  108.00  61.00   0.00   37
 21  ω    125.00 151.00   1.00    3.00    --  108.00  61.00  60.00   26
 22  ω     92.00 104.00   1.00    3.00    --  108.00  61.00 -60.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024437000
_diffrn_orient_matrix_UB_12      0.0829850000
_diffrn_orient_matrix_UB_13      0.0850143000
_diffrn_orient_matrix_UB_21      0.0690592000
_diffrn_orient_matrix_UB_22      -0.0120387000
_diffrn_orient_matrix_UB_23      0.0146894000
_diffrn_orient_matrix_UB_31      0.0110280000
_diffrn_orient_matrix_UB_32      0.0932896000
_diffrn_orient_matrix_UB_33      -0.0737560000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.435
_reflns_Friedel_fraction_full    0.477
_reflns_Friedel_fraction_max     0.477
_reflns_number_gt                3789
_reflns_number_total             4929
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 876 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(18)
_refine_ls_extinction_coef       0.00211(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.021
_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)+(0.0545P)²+0.0553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C22(H22), C23(H23), C6'(H6'), C8'(H8'), C9'(H9'),
 C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C19'(H19'),
 C20'(H20'), C22'(H22'), C23'(H23')
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C24'(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55668(16) 0.2020(3) 0.6200(3) 0.0525(9) Uani 1 1 d . . . . .
C2 C 0.59714(16) 0.2962(3) 0.6288(3) 0.0470(8) Uani 1 1 d . . . . .
C3 C 0.65894(15) 0.2836(3) 0.6350(3) 0.0442(8) Uani 1 1 d . . . . .
C4 C 0.68401(16) 0.1747(3) 0.6342(3) 0.0476(8) Uani 1 1 d . . . . .
C5 C 0.64531(16) 0.0861(3) 0.6234(3) 0.0508(9) Uani 1 1 d . . . . .
C6 C 0.66526(19) -0.0203(3) 0.6225(3) 0.0641(11) Uani 1 1 d . . . . .
H6 H 0.6385 -0.0780 0.6131 0.077 Uiso 1 1 calc R . . . .
C7 C 0.72622(19) -0.0374(3) 0.6360(4) 0.0638(11) Uani 1 1 d . . . . .
C8 C 0.76730(18) 0.0452(3) 0.6486(4) 0.0628(11) Uani 1 1 d . . . . .
H8 H 0.8084 0.0304 0.6577 0.075 Uiso 1 1 calc R . . . .
C9 C 0.74604(18) 0.1512(3) 0.6476(3) 0.0551(9) Uani 1 1 d . . . . .
H9 H 0.7734 0.2083 0.6560 0.066 Uiso 1 1 calc R . . . .
C10 C 0.69934(16) 0.3804(3) 0.6421(3) 0.0521(9) Uani 1 1 d . . . . .
C11 C 0.74363(18) 0.3996(3) 0.5713(4) 0.0627(11) Uani 1 1 d . . . . .
H11 H 0.7493 0.3500 0.5202 0.075 Uiso 1 1 calc R . . . .
C12 C 0.7793(2) 0.4919(4) 0.5762(5) 0.0823(15) Uani 1 1 d . . . . .
H12 H 0.8082 0.5053 0.5277 0.099 Uiso 1 1 calc R . . . .
C13 C 0.7719(3) 0.5643(4) 0.6529(6) 0.099(2) Uani 1 1 d . . . . .
H13 H 0.7963 0.6260 0.6568 0.119 Uiso 1 1 calc R . . . .
C14 C 0.7290(3) 0.5454(4) 0.7229(5) 0.0960(19) Uani 1 1 d . . . . .
H14 H 0.7240 0.5949 0.7743 0.115 Uiso 1 1 calc R . . . .
C15 C 0.6926(2) 0.4541(4) 0.7190(4) 0.0718(12) Uani 1 1 d . . . . .
H15 H 0.6636 0.4420 0.7677 0.086 Uiso 1 1 calc R . . . .
C16 C 0.56732(16) 0.3991(3) 0.6281(3) 0.0493(8) Uani 1 1 d . . . . .
C17 C 0.54031(17) 0.4837(3) 0.6290(3) 0.0517(9) Uani 1 1 d . . . . .
C18 C 0.50959(16) 0.5862(3) 0.6311(3) 0.0494(8) Uani 1 1 d . . . . .
C19 C 0.54067(17) 0.6829(3) 0.6406(3) 0.0586(10) Uani 1 1 d . . . . .
H19 H 0.5828 0.6818 0.6467 0.070 Uiso 1 1 calc R . . . .
C20 C 0.51036(18) 0.7818(3) 0.6414(4) 0.0612(10) Uani 1 1 d . . . . .
H20 H 0.5322 0.8464 0.6471 0.073 Uiso 1 1 calc R . . . .
C21 C 0.44769(17) 0.7847(3) 0.6338(3) 0.0487(8) Uani 1 1 d . . . . .
C22 C 0.41606(16) 0.6883(3) 0.6240(3) 0.0494(8) Uani 1 1 d . . . . .
H22 H 0.3739 0.6899 0.6183 0.059 Uiso 1 1 calc R . . . .
C23 C 0.44585(17) 0.5895(3) 0.6225(3) 0.0472(8) Uani 1 1 d . . . . .
H23 H 0.4239 0.5252 0.6158 0.057 Uiso 1 1 calc R . . . .
C24 C 0.4445(2) 0.9783(3) 0.6365(4) 0.0799(14) Uani 1 1 d . . . . .
H24A H 0.4647 0.9862 0.6988 0.120 Uiso 1 1 calc GR . . . .
H24B H 0.4158 1.0365 0.6282 0.120 Uiso 1 1 calc GR . . . .
H24C H 0.4739 0.9807 0.5842 0.120 Uiso 1 1 calc GR . . . .
F1 F 0.74694(14) -0.14147(17) 0.6366(3) 0.0947(9) Uani 1 1 d . . . . .
O1 O 0.50211(12) 0.2050(2) 0.6159(3) 0.0709(9) Uani 1 1 d . . . . .
O2 O 0.58343(11) 0.1010(2) 0.6141(2) 0.0595(8) Uani 1 1 d . . . . .
O3 O 0.41336(12) 0.8769(2) 0.6339(3) 0.0634(7) Uani 1 1 d . . . . .
C1' C 0.45534(17) 0.4283(3) 0.3902(3) 0.0522(9) Uani 1 1 d . . . . .
C2' C 0.49552(15) 0.5215(3) 0.3783(3) 0.0457(8) Uani 1 1 d . . . . .
C3' C 0.55721(15) 0.5095(3) 0.3725(3) 0.0439(7) Uani 1 1 d . . . . .
C4' C 0.58229(16) 0.4003(3) 0.3722(3) 0.0457(8) Uani 1 1 d . . . . .
C5' C 0.54347(16) 0.3121(3) 0.3832(3) 0.0488(8) Uani 1 1 d . . . . .
C6' C 0.56377(19) 0.2050(3) 0.3829(3) 0.0573(10) Uani 1 1 d . . . . .
H6' H 0.5370 0.1471 0.3916 0.069 Uiso 1 1 calc R . . . .
C7' C 0.6246(2) 0.1882(3) 0.3694(3) 0.0594(10) Uani 1 1 d . . . . .
C8' C 0.66531(19) 0.2710(3) 0.3561(3) 0.0591(10) Uani 1 1 d . . . . .
H8' H 0.7064 0.2563 0.3463 0.071 Uiso 1 1 calc R . . . .
C9' C 0.64430(17) 0.3768(3) 0.3577(3) 0.0538(9) Uani 1 1 d . . . . .
H9' H 0.6716 0.4338 0.3489 0.065 Uiso 1 1 calc R . . . .
C10' C 0.59739(16) 0.6056(3) 0.3667(3) 0.0499(9) Uani 1 1 d . . . . .
C11' C 0.64151(18) 0.6228(3) 0.4391(3) 0.0573(10) Uani 1 1 d . . . . .
H11' H 0.6471 0.5716 0.4889 0.069 Uiso 1 1 calc R . . . .
C12' C 0.6770(2) 0.7160(4) 0.4368(4) 0.0775(14) Uani 1 1 d . . . . .
H12' H 0.7059 0.7278 0.4857 0.093 Uiso 1 1 calc R . . . .
C13' C 0.6698(2) 0.7907(4) 0.3631(6) 0.0930(18) Uani 1 1 d . . . . .
H13' H 0.6937 0.8533 0.3622 0.112 Uiso 1 1 calc R . . . .
C14' C 0.6272(2) 0.7737(4) 0.2899(5) 0.0884(17) Uani 1 1 d . . . . .
H14' H 0.6228 0.8243 0.2393 0.106 Uiso 1 1 calc R . . . .
C15' C 0.5909(2) 0.6812(3) 0.2917(3) 0.0658(11) Uani 1 1 d . . . . .
H15' H 0.5621 0.6700 0.2424 0.079 Uiso 1 1 calc R . . . .
C16' C 0.46586(16) 0.6247(3) 0.3771(3) 0.0502(8) Uani 1 1 d . . . . .
C17' C 0.43945(17) 0.7102(3) 0.3774(3) 0.0507(8) Uani 1 1 d . . . . .
C18' C 0.40801(16) 0.8122(3) 0.3795(3) 0.0476(8) Uani 1 1 d . . . . .
C19' C 0.43883(17) 0.9092(3) 0.3702(4) 0.0641(11) Uani 1 1 d . . . . .
H19' H 0.4806 0.9086 0.3599 0.077 Uiso 1 1 calc R . . . .
C20' C 0.40834(18) 1.0076(3) 0.3759(5) 0.0742(13) Uani 1 1 d . . . . .
H20' H 0.4297 1.0726 0.3695 0.089 Uiso 1 1 calc R . . . .
C21' C 0.34624(17) 1.0093(3) 0.3912(3) 0.0586(10) Uani 1 1 d . . . . .
C22' C 0.31515(17) 0.9130(3) 0.3992(3) 0.0579(10) Uani 1 1 d . . . . .
H22' H 0.2733 0.9138 0.4087 0.070 Uiso 1 1 calc R . . . .
C23' C 0.34531(16) 0.8154(3) 0.3934(3) 0.0535(10) Uani 1 1 d . . . . .
H23' H 0.3236 0.7506 0.3987 0.064 Uiso 1 1 calc R . . . .
C24' C 0.3432(3) 1.2037(3) 0.3999(6) 0.124(3) Uani 1 1 d . . . . .
H24D H 0.3743 1.2038 0.4497 0.187 Uiso 1 1 calc GR . . . .
H24E H 0.3146 1.2610 0.4131 0.187 Uiso 1 1 calc GR . . . .
H24F H 0.3615 1.2151 0.3364 0.187 Uiso 1 1 calc GR . . . .
F1' F 0.64482(13) 0.08385(18) 0.3682(2) 0.0829(8) Uani 1 1 d . . . . .
O1' O 0.40088(13) 0.4314(2) 0.3993(3) 0.0744(10) Uani 1 1 d . . . . .
O2' O 0.48173(11) 0.32631(19) 0.3940(2) 0.0567(7) Uani 1 1 d . . . . .
O3' O 0.31246(14) 1.1014(2) 0.4007(3) 0.0941(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.463(5) . ?
C1 O1 1.202(4) . ?
C1 O2 1.375(4) . ?
C2 C3 1.370(5) . ?
C2 C16 1.424(5) . ?
C3 C4 1.446(5) . ?
C3 C10 1.486(5) . ?
C4 C5 1.390(5) . ?
C4 C9 1.406(5) . ?
C5 C6 1.377(5) . ?
C5 O2 1.379(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.369(6) . ?
C7 C8 1.369(5) . ?
C7 F1 1.357(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(6) . ?
C10 C15 1.388(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.359(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.197(5) . ?
C17 C18 1.429(5) . ?
C18 C19 1.376(5) . ?
C18 C23 1.407(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(5) . ?
C21 C22 1.380(5) . ?
C21 O3 1.360(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(5) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 O3 1.421(5) . ?
C1' C2' 1.455(5) . ?
C1' O1' 1.204(4) . ?
C1' O2' 1.381(4) . ?
C2' C3' 1.367(4) . ?
C2' C16' 1.424(4) . ?
C3' C4' 1.450(4) . ?
C3' C10' 1.476(5) . ?
C4' C5' 1.386(5) . ?
C4' C9' 1.408(5) . ?
C5' C6' 1.389(4) . ?
C5' O2' 1.376(4) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.365(6) . ?
C7' C8' 1.367(6) . ?
C7' F1' 1.356(4) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.379(5) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.395(5) . ?
C10' C15' 1.384(5) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.386(6) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.365(8) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.380(8) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.388(6) . ?
C15' H15' 0.9300 . ?
C16' C17' 1.200(5) . ?
C17' C18' 1.431(4) . ?
C18' C19' 1.376(5) . ?
C18' C23' 1.392(5) . ?
C19' H19' 0.9300 . ?
C19' C20' 1.384(5) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.381(5) . ?
C21' C22' 1.371(5) . ?
C21' O3' 1.358(4) . ?
C22' H22' 0.9300 . ?
C22' C23' 1.372(5) . ?
C23' H23' 0.9300 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C24' O3' 1.427(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 126.0(4) . . ?
O1 C1 O2 116.8(4) . . ?
O2 C1 C2 117.2(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 C16 123.8(3) . . ?
C16 C2 C1 114.9(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 C10 120.5(3) . . ?
C4 C3 C10 120.8(3) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 C9 116.5(3) . . ?
C9 C4 C3 124.0(3) . . ?
C6 C5 C4 123.3(3) . . ?
C6 C5 O2 116.1(3) . . ?
O2 C5 C4 120.6(3) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 C5 117.1(4) . . ?
C7 C6 H6 121.4 . . ?
C8 C7 C6 123.3(3) . . ?
F1 C7 C6 118.3(4) . . ?
F1 C7 C8 118.4(4) . . ?
C7 C8 H8 120.9 . . ?
C7 C8 C9 118.2(4) . . ?
C9 C8 H8 120.9 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.5(4) . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C3 120.7(4) . . ?
C11 C10 C15 118.9(4) . . ?
C15 C10 C3 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(5) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C2 177.5(4) . . ?
C16 C17 C18 178.4(4) . . ?
C19 C18 C17 121.8(3) . . ?
C19 C18 C23 118.5(3) . . ?
C23 C18 C17 119.6(3) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.1(4) . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.2(3) . . ?
O3 C21 C20 125.1(3) . . ?
O3 C21 C22 115.8(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 120.1 . . ?
C22 C23 C18 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
C1 O2 C5 122.4(3) . . ?
C21 O3 C24 117.5(3) . . ?
O1' C1' C2' 126.2(3) . . ?
O1' C1' O2' 116.3(3) . . ?
O2' C1' C2' 117.5(3) . . ?
C3' C2' C1' 121.6(3) . . ?
C3' C2' C16' 123.4(3) . . ?
C16' C2' C1' 115.0(3) . . ?
C2' C3' C4' 118.5(3) . . ?
C2' C3' C10' 120.7(3) . . ?
C4' C3' C10' 120.8(3) . . ?
C5' C4' C3' 119.2(3) . . ?
C5' C4' C9' 116.9(3) . . ?
C9' C4' C3' 123.9(3) . . ?
C4' C5' C6' 122.7(3) . . ?
O2' C5' C4' 121.3(3) . . ?
O2' C5' C6' 115.9(3) . . ?
C5' C6' H6' 121.4 . . ?
C7' C6' C5' 117.3(4) . . ?
C7' C6' H6' 121.4 . . ?
C6' C7' C8' 123.2(3) . . ?
F1' C7' C6' 117.8(4) . . ?
F1' C7' C8' 119.1(4) . . ?
C7' C8' H8' 120.7 . . ?
C7' C8' C9' 118.6(4) . . ?
C9' C8' H8' 120.7 . . ?
C4' C9' H9' 119.3 . . ?
C8' C9' C4' 121.3(4) . . ?
C8' C9' H9' 119.3 . . ?
C11' C10' C3' 120.0(4) . . ?
C15' C10' C3' 120.9(4) . . ?
C15' C10' C11' 119.1(4) . . ?
C10' C11' H11' 120.0 . . ?
C12' C11' C10' 120.0(4) . . ?
C12' C11' H11' 120.0 . . ?
C11' C12' H12' 119.8 . . ?
C13' C12' C11' 120.4(5) . . ?
C13' C12' H12' 119.8 . . ?
C12' C13' H13' 119.9 . . ?
C12' C13' C14' 120.2(5) . . ?
C14' C13' H13' 119.9 . . ?
C13' C14' H14' 119.9 . . ?
C13' C14' C15' 120.1(5) . . ?
C15' C14' H14' 119.9 . . ?
C10' C15' C14' 120.1(5) . . ?
C10' C15' H15' 119.9 . . ?
C14' C15' H15' 119.9 . . ?
C17' C16' C2' 178.1(4) . . ?
C16' C17' C18' 179.1(5) . . ?
C19' C18' C17' 121.2(3) . . ?
C19' C18' C23' 118.4(3) . . ?
C23' C18' C17' 120.4(3) . . ?
C18' C19' H19' 119.6 . . ?
C18' C19' C20' 120.8(4) . . ?
C20' C19' H19' 119.6 . . ?
C19' C20' H20' 120.0 . . ?
C21' C20' C19' 120.1(4) . . ?
C21' C20' H20' 120.0 . . ?
C22' C21' C20' 119.4(3) . . ?
O3' C21' C20' 124.6(4) . . ?
O3' C21' C22' 116.0(3) . . ?
C21' C22' H22' 119.7 . . ?
C21' C22' C23' 120.5(4) . . ?
C23' C22' H22' 119.7 . . ?
C18' C23' H23' 119.6 . . ?
C22' C23' C18' 120.7(3) . . ?
C22' C23' H23' 119.6 . . ?
H24D C24' H24E 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
O3' C24' H24D 109.5 . . ?
O3' C24' H24E 109.5 . . ?
O3' C24' H24F 109.5 . . ?
C5' O2' C1' 121.7(3) . . ?
C21' O3' C24' 118.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.8(6) . . . . ?
C1 C2 C3 C10 178.9(4) . . . . ?
C2 C1 O2 C5 4.8(6) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C2 C3 C4 C9 -175.0(4) . . . . ?
C2 C3 C10 C11 -120.4(4) . . . . ?
C2 C3 C10 C15 58.4(5) . . . . ?
C3 C4 C5 C6 -179.5(4) . . . . ?
C3 C4 C5 O2 -0.4(6) . . . . ?
C3 C4 C9 C8 178.3(4) . . . . ?
C3 C10 C11 C12 177.3(4) . . . . ?
C3 C10 C15 C14 -177.8(4) . . . . ?
C4 C3 C10 C11 59.3(5) . . . . ?
C4 C3 C10 C15 -121.9(4) . . . . ?
C4 C5 C6 C7 2.0(7) . . . . ?
C4 C5 O2 C1 -3.4(6) . . . . ?
C5 C4 C9 C8 0.8(6) . . . . ?
C5 C6 C7 C8 -1.0(8) . . . . ?
C5 C6 C7 F1 179.2(4) . . . . ?
C6 C5 O2 C1 175.8(4) . . . . ?
C6 C7 C8 C9 0.0(8) . . . . ?
C7 C8 C9 C4 0.1(7) . . . . ?
C9 C4 C5 C6 -1.9(6) . . . . ?
C9 C4 C5 O2 177.2(4) . . . . ?
C10 C3 C4 C5 -177.3(4) . . . . ?
C10 C3 C4 C9 5.2(6) . . . . ?
C10 C11 C12 C13 1.5(7) . . . . ?
C11 C10 C15 C14 1.0(6) . . . . ?
C11 C12 C13 C14 -0.9(8) . . . . ?
C12 C13 C14 C15 0.4(9) . . . . ?
C13 C14 C15 C10 -0.5(8) . . . . ?
C15 C10 C11 C12 -1.5(6) . . . . ?
C16 C2 C3 C4 -179.5(4) . . . . ?
C16 C2 C3 C10 0.3(6) . . . . ?
C17 C18 C19 C20 179.2(4) . . . . ?
C17 C18 C23 C22 -179.7(4) . . . . ?
C18 C19 C20 C21 0.8(7) . . . . ?
C19 C18 C23 C22 -0.1(6) . . . . ?
C19 C20 C21 C22 -0.9(7) . . . . ?
C19 C20 C21 O3 179.9(4) . . . . ?
C20 C21 C22 C23 0.5(7) . . . . ?
C20 C21 O3 C24 3.8(7) . . . . ?
C21 C22 C23 C18 0.0(6) . . . . ?
C22 C21 O3 C24 -175.5(4) . . . . ?
C23 C18 C19 C20 -0.3(7) . . . . ?
F1 C7 C8 C9 179.8(4) . . . . ?
O1 C1 C2 C3 178.6(4) . . . . ?
O1 C1 C2 C16 -2.6(7) . . . . ?
O1 C1 O2 C5 -176.3(4) . . . . ?
O2 C1 C2 C3 -2.7(6) . . . . ?
O2 C1 C2 C16 176.1(3) . . . . ?
O2 C5 C6 C7 -177.2(4) . . . . ?
O3 C21 C22 C23 179.8(3) . . . . ?
C1' C2' C3' C4' 3.7(6) . . . . ?
C1' C2' C3' C10' -176.2(4) . . . . ?
C2' C1' O2' C5' -2.5(6) . . . . ?
C2' C3' C4' C5' -3.5(6) . . . . ?
C2' C3' C4' C9' 174.1(4) . . . . ?
C2' C3' C10' C11' 120.5(4) . . . . ?
C2' C3' C10' C15' -57.7(5) . . . . ?
C3' C4' C5' C6' 179.4(4) . . . . ?
C3' C4' C5' O2' 0.3(6) . . . . ?
C3' C4' C9' C8' -178.6(4) . . . . ?
C3' C10' C11' C12' -176.4(4) . . . . ?
C3' C10' C15' C14' 177.0(4) . . . . ?
C4' C3' C10' C11' -59.4(5) . . . . ?
C4' C3' C10' C15' 122.4(4) . . . . ?
C4' C5' C6' C7' -1.1(7) . . . . ?
C4' C5' O2' C1' 2.7(6) . . . . ?
C5' C4' C9' C8' -1.0(6) . . . . ?
C5' C6' C7' C8' -0.2(7) . . . . ?
C5' C6' C7' F1' -179.5(4) . . . . ?
C6' C5' O2' C1' -176.5(4) . . . . ?
C6' C7' C8' C9' 0.8(7) . . . . ?
C7' C8' C9' C4' -0.2(6) . . . . ?
C9' C4' C5' C6' 1.7(6) . . . . ?
C9' C4' C5' O2' -177.5(4) . . . . ?
C10' C3' C4' C5' 176.4(4) . . . . ?
C10' C3' C4' C9' -6.0(6) . . . . ?
C10' C11' C12' C13' -1.1(7) . . . . ?
C11' C10' C15' C14' -1.1(6) . . . . ?
C11' C12' C13' C14' -0.2(8) . . . . ?
C12' C13' C14' C15' 0.9(9) . . . . ?
C13' C14' C15' C10' -0.2(8) . . . . ?
C15' C10' C11' C12' 1.8(6) . . . . ?
C16' C2' C3' C4' -178.7(4) . . . . ?
C16' C2' C3' C10' 1.4(6) . . . . ?
C17' C18' C19' C20' -177.6(5) . . . . ?
C17' C18' C23' C22' 177.5(4) . . . . ?
C18' C19' C20' C21' 0.0(9) . . . . ?
C19' C18' C23' C22' -1.1(7) . . . . ?
C19' C20' C21' C22' -0.9(9) . . . . ?
C19' C20' C21' O3' 178.0(5) . . . . ?
C20' C21' C22' C23' 0.8(8) . . . . ?
C20' C21' O3' C24' -3.3(9) . . . . ?
C21' C22' C23' C18' 0.2(7) . . . . ?
C22' C21' O3' C24' 175.7(5) . . . . ?
C23' C18' C19' C20' 0.9(7) . . . . ?
F1' C7' C8' C9' -179.9(4) . . . . ?
O1' C1' C2' C3' 177.3(4) . . . . ?
O1' C1' C2' C16' -0.5(7) . . . . ?
O1' C1' O2' C5' 179.2(4) . . . . ?
O2' C1' C2' C3' -0.9(6) . . . . ?
O2' C1' C2' C16' -178.6(3) . . . . ?
O2' C5' C6' C7' 178.1(4) . . . . ?
O3' C21' C22' C23' -178.2(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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.932
####################################################################### 
# 
# 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_201911284
_database_code_depnum_ccdc_archive 'CCDC 1966836'
loop_
_audit_author_name
_audit_author_address
'xinjie Wu'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 O2'
_chemical_formula_sum            'C23 H14 O2'
_chemical_formula_weight         322.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4
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                   10.9195(8)
_cell_length_b                   11.7513(7)
_cell_length_c                   14.2060(6)
_cell_angle_alpha                87.690(5)
_cell_angle_beta                 77.763(5)
_cell_angle_gamma                71.943(6)
_cell_volume                     1693.11(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5420
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.16
_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  0.0230
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11792
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.958
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  30.00   87
  2  ω   -105.00  38.00   1.00    1.00    --  -33.50   0.00  90.00  143
  3  ω   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 -90.00   76
  4  ω    -52.00 -18.00   1.00    1.00    --  -33.50   0.00  90.00   34
  5  ω     35.00  72.00   1.00    1.00    --   36.47 -99.00 -60.00   37
  6  ω     11.00  72.00   1.00    1.00    --   36.47 -99.00  90.00   61
  7  ω     -4.00  73.00   1.00    1.00    --   36.47 -99.00-150.00   77
  8  ω     26.00  62.00   1.00    1.00    --   36.47 -77.00  90.00   36
  9  ω     71.00  96.00   1.00    1.00    --   36.47 178.00   0.00   25
 10  ω    -27.00  19.00   1.00    1.00    --   36.47 -77.00  90.00   46
 11  ω    -31.00  46.00   1.00    1.00    --   36.47 -37.00 120.00   77
 12  ω     64.00 108.00   1.00    1.00    --   36.47 178.00  90.00   44
 13  ω     86.00 136.00   1.00    7.00    --  108.00  30.00   0.00   50
 14  ω     39.00 132.00   1.00    7.00    --  108.00 -77.00  60.00   93
 15  ω     38.00 125.00   1.00    7.00    --  108.00 -30.00   0.00   87
 16  ω    100.00 178.00   1.00    7.00    --  108.00  30.00  90.00   78
 17  ω     39.00 127.00   1.00    7.00    --  108.00 -45.00 -90.00   88
 18  ω     37.00  85.00   1.00    7.00    --  108.00 -30.00 120.00   48
 19  ω     54.00 100.00   1.00    7.00    --  108.00 -94.00 -30.00   46
 20  ω     38.00 116.00   1.00    7.00    --  108.00 -45.00-180.00   78
 21  ω     94.00 120.00   1.00    7.00    --  108.00  45.00 -90.00   26
 22  ω     60.00  93.00   1.00    7.00    --  108.00 -94.00 -90.00   33
 23  ω     84.00 111.00   1.00    7.00    --  108.00-111.00-180.00   27
 24  ω    114.00 177.00   1.00    7.00    --  108.00  15.00-150.00   63
 25  ω     40.00  66.00   1.00    7.00    --  108.00-111.00-180.00   26
 26  ω     58.00 110.00   1.00    7.00    --  108.00 -94.00  30.00   52
 27  ω     64.00  95.00   1.00    7.00    --  108.00  15.00-150.00   31
 28  ω     37.00 112.00   1.00    7.00    --  108.00-111.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0784980000
_diffrn_orient_matrix_UB_12      -0.1280965000
_diffrn_orient_matrix_UB_13      0.0219370000
_diffrn_orient_matrix_UB_21      0.1280679000
_diffrn_orient_matrix_UB_22      0.0344724000
_diffrn_orient_matrix_UB_23      -0.0230228000
_diffrn_orient_matrix_UB_31      -0.0217286000
_diffrn_orient_matrix_UB_32      0.0378166000
_diffrn_orient_matrix_UB_33      0.1063547000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4481
_reflns_number_total             5950
_reflns_odcompleteness_completeness 98.80
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.018
_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)+(0.0717P)²+0.1125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1428
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C6'(H6'), C7'(H7'),
  C8'(H8'), C9'(H9'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'),
 C15'(H15'), C19'(H19'), C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.2451(2) 0.51139(17) 0.59582(13) 0.0609(4) Uani 1 1 d . . . . .
C2 C 1.10386(18) 0.57686(15) 0.61347(12) 0.0535(4) Uani 1 1 d . . . . .
C3 C 1.05842(17) 0.69843(15) 0.61438(11) 0.0513(4) Uani 1 1 d . . . . .
C4 C 1.15237(18) 0.76498(16) 0.59537(12) 0.0544(4) Uani 1 1 d . . . . .
C5 C 1.28593(19) 0.70097(18) 0.58085(13) 0.0597(4) Uani 1 1 d . . . . .
C6 C 1.3821(2) 0.7575(2) 0.56080(17) 0.0770(6) Uani 1 1 d . . . . .
H6 H 1.4708 0.7132 0.5516 0.092 Uiso 1 1 calc R . . . .
C7 C 1.3449(2) 0.8797(2) 0.55475(19) 0.0846(7) Uani 1 1 d . . . . .
H7 H 1.4088 0.9185 0.5419 0.101 Uiso 1 1 calc R . . . .
C8 C 1.2137(3) 0.9458(2) 0.56745(19) 0.0814(6) Uani 1 1 d . . . . .
H8 H 1.1898 1.0286 0.5626 0.098 Uiso 1 1 calc R . . . .
C9 C 1.1177(2) 0.88977(18) 0.58733(15) 0.0669(5) Uani 1 1 d . . . . .
H9 H 1.0294 0.9350 0.5954 0.080 Uiso 1 1 calc R . . . .
C10 C 0.91422(17) 0.76310(15) 0.63399(13) 0.0533(4) Uani 1 1 d . . . . .
C11 C 0.8546(2) 0.84013(17) 0.71341(15) 0.0648(5) Uani 1 1 d . . . . .
H11 H 0.9052 0.8538 0.7542 0.078 Uiso 1 1 calc R . . . .
C12 C 0.7199(2) 0.8968(2) 0.73223(18) 0.0777(6) Uani 1 1 d . . . . .
H12 H 0.6801 0.9472 0.7863 0.093 Uiso 1 1 calc R . . . .
C13 C 0.6447(2) 0.8788(2) 0.6711(2) 0.0828(7) Uani 1 1 d . . . . .
H13 H 0.5544 0.9173 0.6835 0.099 Uiso 1 1 calc R . . . .
C14 C 0.7041(2) 0.8033(2) 0.59147(19) 0.0758(6) Uani 1 1 d . . . . .
H14 H 0.6537 0.7917 0.5497 0.091 Uiso 1 1 calc R . . . .
C15 C 0.83757(19) 0.74493(17) 0.57328(15) 0.0621(4) Uani 1 1 d . . . . .
H15 H 0.8765 0.6931 0.5200 0.075 Uiso 1 1 calc R . . . .
C16 C 1.01892(19) 0.50393(15) 0.63004(13) 0.0568(4) Uani 1 1 d . . . . .
C17 C 0.9465(2) 0.44334(16) 0.64197(13) 0.0577(4) Uani 1 1 d . . . . .
C18 C 0.85837(19) 0.37383(16) 0.65100(12) 0.0558(4) Uani 1 1 d . . . . .
C19 C 0.7270(2) 0.42782(19) 0.64634(15) 0.0684(5) Uani 1 1 d . . . . .
H19 H 0.6954 0.5100 0.6387 0.082 Uiso 1 1 calc R . . . .
C20 C 0.6432(2) 0.3587(3) 0.65305(17) 0.0826(6) Uani 1 1 d . . . . .
H20 H 0.5558 0.3948 0.6490 0.099 Uiso 1 1 calc R . . . .
C21 C 0.6880(3) 0.2377(2) 0.66555(16) 0.0802(6) Uani 1 1 d . . . . .
H21 H 0.6310 0.1921 0.6706 0.096 Uiso 1 1 calc R . . . .
C22 C 0.8170(3) 0.18411(19) 0.67061(15) 0.0743(6) Uani 1 1 d . . . . .
H22 H 0.8473 0.1020 0.6792 0.089 Uiso 1 1 calc R . . . .
C23 C 0.9027(2) 0.25112(17) 0.66307(13) 0.0628(5) Uani 1 1 d . . . . .
H23 H 0.9902 0.2138 0.6661 0.075 Uiso 1 1 calc R . . . .
O1 O 1.29296(16) 0.40455(13) 0.59211(13) 0.0816(4) Uani 1 1 d . . . . .
O2 O 1.32945(13) 0.57845(12) 0.58248(10) 0.0661(3) Uani 1 1 d . . . . .
C1' C 1.2036(2) 0.84375(18) 0.09788(13) 0.0621(5) Uani 1 1 d . . . . .
C2' C 1.06218(18) 0.86155(16) 0.10946(12) 0.0550(4) Uani 1 1 d . . . . .
C3' C 1.01431(18) 0.76734(16) 0.10855(12) 0.0532(4) Uani 1 1 d . . . . .
C4' C 1.10570(18) 0.64749(16) 0.09678(12) 0.0562(4) Uani 1 1 d . . . . .
C5' C 1.2392(2) 0.63237(18) 0.08784(13) 0.0616(5) Uani 1 1 d . . . . .
C6' C 1.3326(2) 0.5210(2) 0.07745(16) 0.0789(6) Uani 1 1 d . . . . .
H6' H 1.4209 0.5136 0.0732 0.095 Uiso 1 1 calc R . . . .
C7' C 1.2937(3) 0.4208(2) 0.0734(2) 0.0909(8) Uani 1 1 d . . . . .
H7' H 1.3560 0.3453 0.0665 0.109 Uiso 1 1 calc R . . . .
C8' C 1.1630(3) 0.4323(2) 0.0794(2) 0.0886(7) Uani 1 1 d . . . . .
H8' H 1.1373 0.3645 0.0755 0.106 Uiso 1 1 calc R . . . .
C9' C 1.0705(2) 0.54366(19) 0.09126(16) 0.0714(5) Uani 1 1 d . . . . .
H9' H 0.9823 0.5501 0.0957 0.086 Uiso 1 1 calc R . . . .
C10' C 0.87044(18) 0.78741(15) 0.11979(13) 0.0557(4) Uani 1 1 d . . . . .
C11' C 0.8016(2) 0.74067(18) 0.19698(16) 0.0689(5) Uani 1 1 d . . . . .
H11' H 0.8455 0.6959 0.2422 0.083 Uiso 1 1 calc R . . . .
C12' C 0.6677(2) 0.7606(2) 0.20678(19) 0.0829(7) Uani 1 1 d . . . . .
H12' H 0.6219 0.7297 0.2590 0.099 Uiso 1 1 calc R . . . .
C13' C 0.6017(2) 0.8257(2) 0.1400(2) 0.0849(7) Uani 1 1 d . . . . .
H13' H 0.5120 0.8379 0.1465 0.102 Uiso 1 1 calc R . . . .
C14' C 0.6699(2) 0.8728(2) 0.06319(18) 0.0759(6) Uani 1 1 d . . . . .
H14' H 0.6256 0.9168 0.0179 0.091 Uiso 1 1 calc R . . . .
C15' C 0.8036(2) 0.85497(17) 0.05307(15) 0.0643(5) Uani 1 1 d . . . . .
H15' H 0.8484 0.8881 0.0018 0.077 Uiso 1 1 calc R . . . .
C16' C 0.97882(19) 0.98211(17) 0.12541(13) 0.0589(4) Uani 1 1 d . . . . .
C17' C 0.9045(2) 1.08179(18) 0.14004(13) 0.0617(4) Uani 1 1 d . . . . .
C18' C 0.8097(2) 1.19858(17) 0.15593(13) 0.0613(4) Uani 1 1 d . . . . .
C19' C 0.6766(2) 1.2113(2) 0.17616(18) 0.0813(6) Uani 1 1 d . . . . .
H19' H 0.6486 1.1438 0.1793 0.098 Uiso 1 1 calc R . . . .
C20' C 0.5847(3) 1.3240(3) 0.1918(2) 0.1002(9) Uani 1 1 d . . . . .
H20' H 0.4952 1.3319 0.2062 0.120 Uiso 1 1 calc R . . . .
C21' C 0.6249(3) 1.4240(3) 0.18605(19) 0.0964(9) Uani 1 1 d . . . . .
H21' H 0.5629 1.4997 0.1956 0.116 Uiso 1 1 calc R . . . .
C22' C 0.7559(3) 1.4123(2) 0.16631(17) 0.0852(7) Uani 1 1 d . . . . .
H22' H 0.7830 1.4802 0.1631 0.102 Uiso 1 1 calc R . . . .
C23' C 0.8486(2) 1.30063(18) 0.15096(15) 0.0711(5) Uani 1 1 d . . . . .
H23' H 0.9377 1.2938 0.1372 0.085 Uiso 1 1 calc R . . . .
O1' O 1.25292(17) 0.92240(15) 0.09721(13) 0.0825(4) Uani 1 1 d . . . . .
O2' O 1.28550(13) 0.72887(13) 0.08794(10) 0.0680(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
C1 C2 1.466(3) . ?
C1 O1 1.200(2) . ?
C1 O2 1.367(3) . ?
C2 C3 1.359(2) . ?
C2 C16 1.426(3) . ?
C3 C4 1.449(2) . ?
C3 C10 1.491(2) . ?
C4 C5 1.393(3) . ?
C4 C9 1.403(3) . ?
C5 C6 1.385(3) . ?
C5 O2 1.370(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 C15 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.201(3) . ?
C17 C18 1.427(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.388(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.370(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.369(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9300 . ?
C1' C2' 1.467(3) . ?
C1' O1' 1.204(3) . ?
C1' O2' 1.362(3) . ?
C2' C3' 1.365(3) . ?
C2' C16' 1.423(3) . ?
C3' C4' 1.444(3) . ?
C3' C10' 1.489(3) . ?
C4' C5' 1.391(3) . ?
C4' C9' 1.398(3) . ?
C5' C6' 1.378(3) . ?
C5' O2' 1.377(3) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.376(4) . ?
C7' H7' 0.9300 . ?
C7' C8' 1.376(4) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.375(3) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.388(3) . ?
C10' C15' 1.391(3) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.385(3) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.376(3) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.383(4) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.385(3) . ?
C15' H15' 0.9300 . ?
C16' C17' 1.197(3) . ?
C17' C18' 1.432(3) . ?
C18' C19' 1.383(3) . ?
C18' C23' 1.385(3) . ?
C19' H19' 0.9300 . ?
C19' C20' 1.384(4) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.370(5) . ?
C21' H21' 0.9300 . ?
C21' C22' 1.361(4) . ?
C22' H22' 0.9300 . ?
C22' C23' 1.378(3) . ?
C23' H23' 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
O1 C1 C2 125.8(2) . . ?
O1 C1 O2 117.33(19) . . ?
O2 C1 C2 116.86(16) . . ?
C3 C2 C1 121.82(17) . . ?
C3 C2 C16 122.95(17) . . ?
C16 C2 C1 115.23(16) . . ?
C2 C3 C4 119.00(16) . . ?
C2 C3 C10 120.86(16) . . ?
C4 C3 C10 120.14(15) . . ?
C5 C4 C3 118.12(17) . . ?
C5 C4 C9 117.70(18) . . ?
C9 C4 C3 124.14(17) . . ?
C6 C5 C4 121.78(19) . . ?
O2 C5 C4 121.86(17) . . ?
O2 C5 C6 116.33(18) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.1(2) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.7(2) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C3 120.91(17) . . ?
C15 C10 C3 119.95(16) . . ?
C15 C10 C11 119.14(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.31(19) . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C2 178.5(2) . . ?
C16 C17 C18 176.68(19) . . ?
C19 C18 C17 120.50(17) . . ?
C23 C18 C17 120.58(18) . . ?
C23 C18 C19 118.92(19) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C1 O2 C5 122.24(15) . . ?
O1' C1' C2' 125.3(2) . . ?
O1' C1' O2' 117.49(19) . . ?
O2' C1' C2' 117.25(17) . . ?
C3' C2' C1' 121.59(17) . . ?
C3' C2' C16' 122.59(18) . . ?
C16' C2' C1' 115.77(17) . . ?
C2' C3' C4' 118.82(17) . . ?
C2' C3' C10' 120.74(16) . . ?
C4' C3' C10' 120.44(16) . . ?
C5' C4' C3' 118.71(18) . . ?
C5' C4' C9' 116.62(18) . . ?
C9' C4' C3' 124.66(19) . . ?
C6' C5' C4' 122.3(2) . . ?
O2' C5' C4' 121.48(17) . . ?
O2' C5' C6' 116.2(2) . . ?
C5' C6' H6' 120.4 . . ?
C7' C6' C5' 119.3(2) . . ?
C7' C6' H6' 120.4 . . ?
C6' C7' H7' 119.9 . . ?
C8' C7' C6' 120.1(2) . . ?
C8' C7' H7' 119.9 . . ?
C7' C8' H8' 120.0 . . ?
C9' C8' C7' 120.1(2) . . ?
C9' C8' H8' 120.0 . . ?
C4' C9' H9' 119.2 . . ?
C8' C9' C4' 121.5(2) . . ?
C8' C9' H9' 119.2 . . ?
C11' C10' C3' 120.69(17) . . ?
C11' C10' C15' 119.47(18) . . ?
C15' C10' C3' 119.83(17) . . ?
C10' C11' H11' 120.0 . . ?
C12' C11' C10' 120.1(2) . . ?
C12' C11' H11' 120.0 . . ?
C11' C12' H12' 119.7 . . ?
C13' C12' C11' 120.6(2) . . ?
C13' C12' H12' 119.7 . . ?
C12' C13' H13' 120.2 . . ?
C12' C13' C14' 119.5(2) . . ?
C14' C13' H13' 120.2 . . ?
C13' C14' H14' 119.7 . . ?
C13' C14' C15' 120.6(2) . . ?
C15' C14' H14' 119.7 . . ?
C10' C15' H15' 120.1 . . ?
C14' C15' C10' 119.8(2) . . ?
C14' C15' H15' 120.1 . . ?
C17' C16' C2' 177.4(2) . . ?
C16' C17' C18' 176.6(2) . . ?
C19' C18' C17' 120.1(2) . . ?
C19' C18' C23' 118.6(2) . . ?
C23' C18' C17' 121.3(2) . . ?
C18' C19' H19' 119.9 . . ?
C18' C19' C20' 120.3(3) . . ?
C20' C19' H19' 119.9 . . ?
C19' C20' H20' 119.9 . . ?
C21' C20' C19' 120.3(3) . . ?
C21' C20' H20' 119.9 . . ?
C20' C21' H21' 120.1 . . ?
C22' C21' C20' 119.8(2) . . ?
C22' C21' H21' 120.1 . . ?
C21' C22' H22' 119.7 . . ?
C21' C22' C23' 120.6(3) . . ?
C23' C22' H22' 119.7 . . ?
C18' C23' H23' 119.8 . . ?
C22' C23' C18' 120.4(2) . . ?
C22' C23' H23' 119.8 . . ?
C1' O2' C5' 122.14(16) . . ?

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 1.3(2) . . . . ?
C1 C2 C3 C10 -179.05(16) . . . . ?
C2 C1 O2 C5 -3.1(3) . . . . ?
C2 C3 C4 C5 -2.6(2) . . . . ?
C2 C3 C4 C9 175.08(17) . . . . ?
C2 C3 C10 C11 118.0(2) . . . . ?
C2 C3 C10 C15 -60.9(2) . . . . ?
C3 C4 C5 C6 178.96(18) . . . . ?
C3 C4 C5 O2 1.2(3) . . . . ?
C3 C4 C9 C8 -178.87(19) . . . . ?
C3 C10 C11 C12 -178.08(19) . . . . ?
C3 C10 C15 C14 179.30(19) . . . . ?
C4 C3 C10 C11 -62.3(2) . . . . ?
C4 C3 C10 C15 118.78(19) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 O2 C1 1.8(3) . . . . ?
C5 C4 C9 C8 -1.2(3) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C5 O2 C1 -176.13(18) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C9 C4 C5 O2 -176.69(17) . . . . ?
C10 C3 C4 C5 177.74(15) . . . . ?
C10 C3 C4 C9 -4.6(3) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C11 C10 C15 C14 0.4(3) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C10 -1.2(3) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C16 C2 C3 C4 -179.12(16) . . . . ?
C16 C2 C3 C10 0.5(3) . . . . ?
C17 C18 C19 C20 178.54(18) . . . . ?
C17 C18 C23 C22 -179.21(17) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C18 C23 C22 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
O1 C1 C2 C3 -178.54(19) . . . . ?
O1 C1 C2 C16 1.9(3) . . . . ?
O1 C1 O2 C5 176.97(17) . . . . ?
O2 C1 C2 C3 1.5(3) . . . . ?
O2 C1 C2 C16 -178.12(15) . . . . ?
O2 C5 C6 C7 177.7(2) . . . . ?
C1' C2' C3' C4' 0.6(3) . . . . ?
C1' C2' C3' C10' -179.59(16) . . . . ?
C2' C1' O2' C5' 0.5(2) . . . . ?
C2' C3' C4' C5' 0.7(2) . . . . ?
C2' C3' C4' C9' -177.68(18) . . . . ?
C2' C3' C10' C11' -118.7(2) . . . . ?
C2' C3' C10' C15' 60.5(2) . . . . ?
C3' C4' C5' C6' 179.26(18) . . . . ?
C3' C4' C5' O2' -1.4(3) . . . . ?
C3' C4' C9' C8' 179.6(2) . . . . ?
C3' C10' C11' C12' 179.7(2) . . . . ?
C3' C10' C15' C14' 179.49(19) . . . . ?
C4' C3' C10' C11' 61.2(2) . . . . ?
C4' C3' C10' C15' -119.68(19) . . . . ?
C4' C5' C6' C7' 1.6(3) . . . . ?
C4' C5' O2' C1' 0.8(3) . . . . ?
C5' C4' C9' C8' 1.2(3) . . . . ?
C5' C6' C7' C8' 0.2(4) . . . . ?
C6' C5' O2' C1' -179.83(17) . . . . ?
C6' C7' C8' C9' -1.2(4) . . . . ?
C7' C8' C9' C4' 0.5(4) . . . . ?
C9' C4' C5' C6' -2.2(3) . . . . ?
C9' C4' C5' O2' 177.10(17) . . . . ?
C10' C3' C4' C5' -179.12(16) . . . . ?
C10' C3' C4' C9' 2.5(3) . . . . ?
C10' C11' C12' C13' 0.6(4) . . . . ?
C11' C10' C15' C14' -1.3(3) . . . . ?
C11' C12' C13' C14' -0.8(4) . . . . ?
C12' C13' C14' C15' 0.0(4) . . . . ?
C13' C14' C15' C10' 1.1(3) . . . . ?
C15' C10' C11' C12' 0.5(3) . . . . ?
C16' C2' C3' C4' -176.84(15) . . . . ?
C16' C2' C3' C10' 3.0(3) . . . . ?
C17' C18' C19' C20' 179.9(2) . . . . ?
C17' C18' C23' C22' 179.89(19) . . . . ?
C18' C19' C20' C21' 0.9(4) . . . . ?
C19' C18' C23' C22' 0.2(3) . . . . ?
C19' C20' C21' C22' -1.0(4) . . . . ?
C20' C21' C22' C23' 0.7(4) . . . . ?
C21' C22' C23' C18' -0.3(3) . . . . ?
C23' C18' C19' C20' -0.5(3) . . . . ?
O1' C1' C2' C3' 179.41(18) . . . . ?
O1' C1' C2' C16' -3.0(3) . . . . ?
O1' C1' O2' C5' 179.94(17) . . . . ?
O2' C1' C2' C3' -1.2(3) . . . . ?
O2' C1' C2' C16' 176.40(15) . . . . ?
O2' C5' C6' C7' -177.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.872
