# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

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

data_201911294
_database_code_depnum_ccdc_archive 'CCDC 2026429'
loop_
_audit_author_name
_audit_author_address
'Xi Jinhu'
;Zhengzhou university
China
;
_audit_update_record             
;
2020-08-31 deposited with the CCDC.	2021-06-24 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         'C25 H18 O4'
_chemical_formula_sum            'C25 H18 O4'
_chemical_formula_weight         382.39
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.5609(6)
_cell_length_b                   9.3002(4)
_cell_length_c                   14.7714(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.995(4)
_cell_angle_gamma                90
_cell_volume                     1992.74(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1967
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6180
_cell_measurement_theta_min      5.6300
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93490
_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       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.089
_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   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00 -90.00   87
  2  ω    -57.00 -32.00   1.00    1.00    --  -33.50 178.00 -30.00   25
  3  ω     -3.00  71.00   1.00    1.00    --   36.47 -99.00 120.00   74
  4  ω     33.00  59.00   1.00    1.00    --   36.47 -99.00 150.00   26
  5  ω    -31.00   4.00   1.00    1.00    --   36.47 -77.00-120.00   35
  6  ω     12.00  78.00   1.00    1.00    --   36.47  77.00  30.00   66
  7  ω    -25.00  91.00   1.00    1.00    --   36.47   0.00  90.00  116
  8  ω     39.00 117.00   1.00    7.50    --  108.00 -45.00-150.00   78
  9  ω    107.00 141.00   1.00    7.50    --  108.00 111.00 120.00   34
 10  ω     86.00 176.00   1.00    7.50    --  108.00  30.00 -60.00   90
 11  ω    135.00 177.00   1.00    7.50    --  108.00  30.00  30.00   42
 12  ω     62.00 102.00   1.00    7.50    --  108.00 -94.00 -60.00   40
 13  ω    101.00 127.00   1.00    7.50    --  108.00  30.00  30.00   26
 14  ω     72.00 106.00   1.00    7.50    --  108.00 -94.00-150.00   34
 15  ω     42.00 104.00   1.00    7.50    --  108.00 -45.00 120.00   62
 16  ω     61.00 128.00   1.00    7.50    --  108.00 -45.00 -90.00   67
;
_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      0.0690663000
_diffrn_orient_matrix_UB_12      0.0591311000
_diffrn_orient_matrix_UB_13      0.0758756000
_diffrn_orient_matrix_UB_21      0.0770654000
_diffrn_orient_matrix_UB_22      -0.0052414000
_diffrn_orient_matrix_UB_23      -0.0650151000
_diffrn_orient_matrix_UB_31      -0.0237555000
_diffrn_orient_matrix_UB_32      0.1547193000
_diffrn_orient_matrix_UB_33      -0.0311992000
_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                2600
_reflns_number_total             3554
_reflns_odcompleteness_completeness 99.82
_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         0.133
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.028
_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)+(0.0630P)²+0.1648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1383
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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 -0.07075(16) 0.6390(2) 0.19635(16) 0.0688(6) Uani 1 1 d . . . . .
H1 H -0.0515 0.6708 0.2546 0.083 Uiso 1 1 calc R . . . .
C2 C -0.12267(18) 0.7278(3) 0.13716(19) 0.0823(7) Uani 1 1 d . . . . .
H2 H -0.1390 0.8189 0.1561 0.099 Uiso 1 1 calc R . . . .
C3 C -0.15048(19) 0.6826(3) 0.05041(19) 0.0869(7) Uani 1 1 d . . . . .
H3 H -0.1845 0.7437 0.0105 0.104 Uiso 1 1 calc R . . . .
C4 C -0.12789(17) 0.5470(3) 0.02277(17) 0.0845(7) Uani 1 1 d . . . . .
H4 H -0.1472 0.5163 -0.0357 0.101 Uiso 1 1 calc R . . . .
C5 C -0.07664(16) 0.4560(3) 0.08147(16) 0.0728(6) Uani 1 1 d . . . . .
H5 H -0.0618 0.3641 0.0626 0.087 Uiso 1 1 calc R . . . .
C6 C -0.04726(14) 0.5020(2) 0.16884(14) 0.0593(5) Uani 1 1 d . . . . .
C7 C 0.00562(16) 0.4016(2) 0.23021(14) 0.0640(5) Uani 1 1 d . . . . .
C8 C 0.05471(15) 0.4544(2) 0.32051(15) 0.0622(5) Uani 1 1 d . . . . .
C9 C -0.05878(14) 0.3442(2) 0.41376(13) 0.0592(5) Uani 1 1 d . . . . .
C10 C 0.03868(14) 0.3650(2) 0.40203(13) 0.0566(4) Uani 1 1 d . . . . .
C11 C 0.10603(13) 0.3072(2) 0.46032(13) 0.0542(4) Uani 1 1 d . . . . .
C12 C 0.07928(13) 0.2164(2) 0.53347(12) 0.0532(4) Uani 1 1 d . . . . .
C13 C -0.01428(13) 0.1970(2) 0.54297(13) 0.0531(4) Uani 1 1 d . . . . .
C14 C -0.04702(14) 0.1092(2) 0.60925(13) 0.0566(4) Uani 1 1 d . . . . .
C15 C 0.01821(15) 0.0354(2) 0.66496(13) 0.0609(5) Uani 1 1 d . . . . .
H15 H -0.0017 -0.0248 0.7096 0.073 Uiso 1 1 calc R . . . .
C16 C 0.11253(15) 0.0474(2) 0.65704(14) 0.0609(5) Uani 1 1 d . . . . .
C17 C 0.14208(14) 0.1382(2) 0.59220(13) 0.0582(5) Uani 1 1 d . . . . .
H17 H 0.2050 0.1482 0.5870 0.070 Uiso 1 1 calc R . . . .
C18 C -0.14883(15) 0.0959(3) 0.61793(16) 0.0695(6) Uani 1 1 d . . . . .
H18A H -0.1747 0.1898 0.6249 0.104 Uiso 1 1 calc GR . . . .
H18B H -0.1588 0.0383 0.6701 0.104 Uiso 1 1 calc GR . . . .
H18C H -0.1780 0.0511 0.5643 0.104 Uiso 1 1 calc GR . . . .
C19 C 0.18055(19) -0.0415(3) 0.71686(17) 0.0809(7) Uani 1 1 d . . . . .
H19A H 0.2009 -0.1216 0.6828 0.121 Uiso 1 1 calc GR . . . .
H19B H 0.1513 -0.0761 0.7684 0.121 Uiso 1 1 calc GR . . . .
H19C H 0.2326 0.0170 0.7373 0.121 Uiso 1 1 calc GR . . . .
C20 C 0.20537(14) 0.3286(2) 0.44717(14) 0.0571(5) Uani 1 1 d . . . . .
C21 C 0.24206(16) 0.2754(2) 0.37029(15) 0.0662(5) Uani 1 1 d . . . . .
H21 H 0.2039 0.2282 0.3260 0.079 Uiso 1 1 calc R . . . .
C22 C 0.33466(18) 0.2918(3) 0.35882(19) 0.0809(7) Uani 1 1 d . . . . .
H22 H 0.3589 0.2545 0.3076 0.097 Uiso 1 1 calc R . . . .
C23 C 0.39078(17) 0.3635(3) 0.4235(2) 0.0905(8) Uani 1 1 d . . . . .
H23 H 0.4530 0.3757 0.4156 0.109 Uiso 1 1 calc R . . . .
C24 C 0.35514(17) 0.4170(3) 0.4995(2) 0.0898(8) Uani 1 1 d . . . . .
H24 H 0.3933 0.4662 0.5427 0.108 Uiso 1 1 calc R . . . .
C25 C 0.26313(16) 0.3986(3) 0.51249(17) 0.0728(6) Uani 1 1 d . . . . .
H25 H 0.2399 0.4332 0.5650 0.087 Uiso 1 1 calc R . . . .
O1 O 0.01931(15) 0.27649(18) 0.21210(12) 0.0913(6) Uani 1 1 d . . . . .
O2 O 0.10805(13) 0.55312(18) 0.32126(12) 0.0841(5) Uani 1 1 d . . . . .
O3 O -0.08110(9) 0.26419(16) 0.48531(9) 0.0601(3) Uani 1 1 d . . . . .
O4 O -0.12050(11) 0.39793(19) 0.36488(11) 0.0765(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 H1 0.9300 . ?
C1 C2 1.379(3) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.471(3) . ?
C7 C8 1.538(3) . ?
C7 O1 1.214(3) . ?
C8 C10 1.498(3) . ?
C8 O2 1.202(3) . ?
C9 C10 1.458(3) . ?
C9 O3 1.355(3) . ?
C9 O4 1.211(2) . ?
C10 C11 1.358(3) . ?
C11 C12 1.451(3) . ?
C11 C20 1.490(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.407(3) . ?
C13 C14 1.391(3) . ?
C13 O3 1.385(2) . ?
C14 C15 1.384(3) . ?
C14 C18 1.504(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(3) . ?
C16 C17 1.374(3) . ?
C16 C19 1.514(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.388(3) . ?
C20 C25 1.386(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.370(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(3) . ?
C25 H25 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
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.9(2) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 122.07(19) . . ?
C5 C6 C7 118.6(2) . . ?
C6 C7 C8 120.68(18) . . ?
O1 C7 C6 124.0(2) . . ?
O1 C7 C8 115.1(2) . . ?
C10 C8 C7 115.24(17) . . ?
O2 C8 C7 120.2(2) . . ?
O2 C8 C10 124.2(2) . . ?
O3 C9 C10 117.89(17) . . ?
O4 C9 C10 123.6(2) . . ?
O4 C9 O3 118.42(19) . . ?
C9 C10 C8 113.00(17) . . ?
C11 C10 C8 125.08(19) . . ?
C11 C10 C9 121.92(19) . . ?
C10 C11 C12 118.46(18) . . ?
C10 C11 C20 121.34(18) . . ?
C12 C11 C20 120.11(17) . . ?
C13 C12 C11 118.59(17) . . ?
C13 C12 C17 117.37(18) . . ?
C17 C12 C11 123.89(18) . . ?
C14 C13 C12 123.02(18) . . ?
O3 C13 C12 121.37(17) . . ?
O3 C13 C14 115.61(17) . . ?
C13 C14 C18 120.59(19) . . ?
C15 C14 C13 116.77(18) . . ?
C15 C14 C18 122.64(19) . . ?
C14 C15 H15 118.6 . . ?
C14 C15 C16 122.8(2) . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C19 120.4(2) . . ?
C17 C16 C15 118.61(19) . . ?
C17 C16 C19 120.9(2) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.43(19) . . ?
C16 C17 H17 119.3 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C11 120.43(18) . . ?
C25 C20 C11 120.62(19) . . ?
C25 C20 C21 118.9(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.9(2) . . ?
C24 C25 H25 120.1 . . ?
C9 O3 C13 121.60(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.2(5) . . . . ?
C1 C6 C7 C8 -13.1(3) . . . . ?
C1 C6 C7 O1 172.1(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -178.2(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C5 C6 C7 C8 168.8(2) . . . . ?
C5 C6 C7 O1 -6.1(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C6 C7 C8 C10 131.9(2) . . . . ?
C6 C7 C8 O2 -54.4(3) . . . . ?
C7 C8 C10 C9 -54.0(2) . . . . ?
C7 C8 C10 C11 125.8(2) . . . . ?
C8 C10 C11 C12 -176.68(18) . . . . ?
C8 C10 C11 C20 -0.2(3) . . . . ?
C9 C10 C11 C12 3.1(3) . . . . ?
C9 C10 C11 C20 179.61(18) . . . . ?
C10 C9 O3 C13 -3.6(3) . . . . ?
C10 C11 C12 C13 -2.5(3) . . . . ?
C10 C11 C12 C17 172.99(18) . . . . ?
C10 C11 C20 C21 -63.1(3) . . . . ?
C10 C11 C20 C25 118.5(2) . . . . ?
C11 C12 C13 C14 178.22(17) . . . . ?
C11 C12 C13 O3 -1.1(3) . . . . ?
C11 C12 C17 C16 -176.20(18) . . . . ?
C11 C20 C21 C22 -178.4(2) . . . . ?
C11 C20 C25 C24 179.7(2) . . . . ?
C12 C11 C20 C21 113.3(2) . . . . ?
C12 C11 C20 C25 -65.0(3) . . . . ?
C12 C13 C14 C15 -2.4(3) . . . . ?
C12 C13 C14 C18 178.18(18) . . . . ?
C12 C13 O3 C9 4.2(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C13 O3 C9 -175.10(17) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C19 -177.0(2) . . . . ?
C15 C16 C17 C12 -1.0(3) . . . . ?
C17 C12 C13 C14 2.4(3) . . . . ?
C17 C12 C13 O3 -176.86(16) . . . . ?
C18 C14 C15 C16 179.98(19) . . . . ?
C19 C16 C17 C12 177.08(19) . . . . ?
C20 C11 C12 C13 -179.06(17) . . . . ?
C20 C11 C12 C17 -3.6(3) . . . . ?
C20 C21 C22 C23 -1.0(4) . . . . ?
C21 C20 C25 C24 1.3(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C23 C24 C25 C20 -1.6(4) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?
O1 C7 C8 C10 -52.8(3) . . . . ?
O1 C7 C8 O2 120.9(3) . . . . ?
O2 C8 C10 C9 132.7(2) . . . . ?
O2 C8 C10 C11 -47.5(3) . . . . ?
O3 C9 C10 C8 179.69(17) . . . . ?
O3 C9 C10 C11 -0.1(3) . . . . ?
O3 C13 C14 C15 176.98(16) . . . . ?
O3 C13 C14 C18 -2.5(3) . . . . ?
O4 C9 C10 C8 -2.7(3) . . . . ?
O4 C9 C10 C11 177.5(2) . . . . ?
O4 C9 O3 C13 178.64(18) . . . . ?

_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 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_202010208
_database_code_depnum_ccdc_archive 'CCDC 2036910'
loop_
_audit_author_name
_audit_author_address
'Xi Jinhu'
;Zhengzhou university
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2020-10-09
_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         'C17 H10 O4'
_chemical_formula_sum            'C17 H10 O4'
_chemical_formula_weight         278.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N4
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.1288(11)
_cell_length_b                   7.3017(9)
_cell_length_c                   13.738(2)
_cell_angle_alpha                94.814(11)
_cell_angle_beta                 90.307(13)
_cell_angle_gamma                112.254(14)
_cell_volume                     658.95(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1750
_cell_measurement_theta_min      6.4440
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85387
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4663
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         6.472
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  90.00   87
  2  ω     57.00 111.00   1.00    1.00    --   36.62 178.00  90.00   54
  3  ω    -35.00 108.00   1.00    1.00    --   36.62   0.00  90.00  143
  4  ω     57.00 111.00   1.00    1.00    --   36.62 178.00 -30.00   54
  5  ω     -4.00  77.00   1.00    1.00    --   36.62 -99.00 -90.00   81
  6  ω     -4.00  77.00   1.00    1.00    --   36.62 -99.00  30.00   81
  7  ω     14.00 107.00   1.00    1.00    --   36.62  37.00  90.00   93
  8  ω     57.00 111.00   1.00    1.00    --   36.62 178.00 -90.00   54
  9  ω     -4.00  77.00   1.00    1.00    --   36.62 -99.00  90.00   81
 10  ω    -32.00  55.00   1.00    1.00    --   36.62 -57.00 120.00   87
 11  ω     14.00 107.00   1.00    1.00    --   36.62  37.00 -30.00   93
 12  ω    106.00 154.00   1.00    3.00    --  108.00 111.00 -60.00   48
 13  ω     79.00 110.00   1.00    3.00    --  108.00-111.00-120.00   31
 14  ω     48.00 122.00   1.00    3.00    --  108.00 -61.00 150.00   74
 15  ω    119.00 165.00   1.00    3.00    --  108.00 111.00 150.00   46
 16  ω     47.00 109.00   1.00    3.00    --  108.00 -94.00 120.00   62
 17  ω    116.00 150.00   1.00    3.00    --  108.00 178.00-180.00   34
 18  ω    114.00 146.00   1.00    3.00    --  108.00 111.00 -90.00   32
 19  ω    143.00 174.00   1.00    3.00    --  108.00  61.00   0.00   31
 20  ω     94.00 121.00   1.00    3.00    --  108.00  61.00   0.00   27
 21  ω     70.00  98.00   1.00    3.00    --  108.00 178.00-180.00   28
 22  ω     43.00 114.00   1.00    3.00    --  108.00 -45.00   0.00   71
 23  ω     73.00 103.00   1.00    3.00    --  108.00-111.00   0.00   30
 24  ω    102.00 127.00   1.00    3.00    --  108.00 111.00  60.00   25
 25  ω    147.00 176.00   1.00    3.00    --  108.00 111.00  60.00   29
 26  ω     38.00  65.00   1.00    3.00    --  108.00-111.00   0.00   27
 27  ω     39.00 148.00   1.00    3.00    --  108.00 -15.00-180.00  109
 28  ω     50.00 128.00   1.00    3.00    --  108.00 -61.00-120.00   78
 29  ω     90.00 176.00   1.00    3.00    --  108.00  30.00-150.00   86
;
_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      -0.0601985000
_diffrn_orient_matrix_UB_12      -0.1479047000
_diffrn_orient_matrix_UB_13      0.0788248000
_diffrn_orient_matrix_UB_21      0.1455523000
_diffrn_orient_matrix_UB_22      0.1605645000
_diffrn_orient_matrix_UB_23      0.0748512000
_diffrn_orient_matrix_UB_31      -0.1726269000
_diffrn_orient_matrix_UB_32      0.0690217000
_diffrn_orient_matrix_UB_33      0.0294833000
_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                1404
_reflns_number_total             2352
_reflns_odcompleteness_completeness 99.62
_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         0.223
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.035
_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)+(0.1090P)²+0.0550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1804
_refine_ls_wR_factor_ref         0.2205
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_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
O1 O 0.2239(3) 0.2084(3) 0.51657(17) 0.0668(6) Uani 1 1 d . . . . .
C1 C 0.7589(5) 0.2891(5) 0.4822(3) 0.0666(9) Uani 1 1 d . . . . .
H1 H 0.8733 0.2954 0.5174 0.080 Uiso 1 1 calc R . . . .
O2 O 0.0304(3) 0.1478(4) 0.6427(2) 0.0824(8) Uani 1 1 d . . . . .
C2 C 0.7705(5) 0.3167(5) 0.3857(3) 0.0709(9) Uani 1 1 d . . . . .
H2 H 0.8931 0.3430 0.3553 0.085 Uiso 1 1 calc R . . . .
O3 O 0.4871(4) 0.1701(4) 0.8308(2) 0.0901(9) Uani 1 1 d . . . . .
C3 C 0.5996(6) 0.3060(5) 0.3315(3) 0.0732(9) Uani 1 1 d . . . . .
H3 H 0.6089 0.3254 0.2654 0.088 Uiso 1 1 calc R . . . .
C4 C 0.4169(5) 0.2665(5) 0.3760(3) 0.0674(9) Uani 1 1 d . . . . .
H4 H 0.3019 0.2564 0.3400 0.081 Uiso 1 1 calc R . . . .
O4 O 0.1664(4) 0.3587(4) 0.8458(2) 0.0884(8) Uani 1 1 d . . . . .
C5 C 0.4075(4) 0.2425(4) 0.4735(3) 0.0594(8) Uani 1 1 d . . . . .
C6 C 0.5758(4) 0.2512(4) 0.5295(2) 0.0575(8) Uani 1 1 d . . . . .
C7 C 0.5546(4) 0.2282(4) 0.6306(3) 0.0585(8) Uani 1 1 d . . . . .
H7 H 0.6655 0.2340 0.6685 0.070 Uiso 1 1 calc R . . . .
C8 C 0.3758(4) 0.1980(4) 0.6732(3) 0.0589(8) Uani 1 1 d . . . . .
C9 C 0.1978(5) 0.1821(5) 0.6131(3) 0.0623(8) Uani 1 1 d . . . . .
C10 C 0.3542(5) 0.1806(5) 0.7785(3) 0.0653(9) Uani 1 1 d . . . . .
C11 C 0.1662(5) 0.1926(5) 0.8286(3) 0.0667(9) Uani 1 1 d . . . . .
C12 C 0.0089(5) 0.0089(5) 0.8575(2) 0.0630(8) Uani 1 1 d . . . . .
C13 C -0.1711(5) 0.0151(6) 0.8915(3) 0.0765(10) Uani 1 1 d . . . . .
H13 H -0.1898 0.1348 0.8974 0.092 Uiso 1 1 calc R . . . .
C14 C -0.3229(6) -0.1560(7) 0.9165(3) 0.0876(12) Uani 1 1 d . . . . .
H14 H -0.4445 -0.1521 0.9386 0.105 Uiso 1 1 calc R . . . .
C15 C -0.2939(7) -0.3328(7) 0.9087(3) 0.0923(13) Uani 1 1 d . . . . .
H15 H -0.3959 -0.4482 0.9259 0.111 Uiso 1 1 calc R . . . .
C16 C -0.1154(7) -0.3389(6) 0.8758(3) 0.0943(13) Uani 1 1 d . . . . .
H16 H -0.0964 -0.4585 0.8710 0.113 Uiso 1 1 calc R . . . .
C17 C 0.0361(6) -0.1695(6) 0.8500(3) 0.0787(10) Uani 1 1 d . . . . .
H17 H 0.1569 -0.1747 0.8274 0.094 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.382(4) . ?
O1 C9 1.359(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.356(5) . ?
C1 C6 1.403(4) . ?
O2 C9 1.204(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(5) . ?
O3 C10 1.215(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(5) . ?
O4 C11 1.216(4) . ?
C5 C6 1.400(4) . ?
C6 C7 1.415(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.354(4) . ?
C8 C9 1.472(4) . ?
C8 C10 1.467(5) . ?
C10 C11 1.538(4) . ?
C11 C12 1.473(5) . ?
C12 C13 1.383(5) . ?
C12 C17 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 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
C9 O1 C5 122.5(2) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(3) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
O1 C5 C6 120.1(3) . . ?
C4 C5 O1 117.7(3) . . ?
C4 C5 C6 122.2(3) . . ?
C1 C6 C7 123.6(3) . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 118.7(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 C10 121.6(3) . . ?
C10 C8 C9 118.7(3) . . ?
O1 C9 C8 117.7(3) . . ?
O2 C9 O1 117.2(3) . . ?
O2 C9 C8 125.1(3) . . ?
O3 C10 C8 122.4(3) . . ?
O3 C10 C11 117.1(3) . . ?
C8 C10 C11 120.3(3) . . ?
O4 C11 C10 115.8(3) . . ?
O4 C11 C12 125.2(3) . . ?
C12 C11 C10 119.0(3) . . ?
C13 C12 C11 119.0(3) . . ?
C17 C12 C11 121.5(3) . . ?
C17 C12 C13 119.5(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.0(4) . . ?
C16 C17 H17 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 C1 -179.1(3) . . . . ?
O1 C5 C6 C7 -1.2(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C1 C6 C7 C8 177.9(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C1 C6 C7 -177.6(3) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
O3 C10 C11 O4 96.7(4) . . . . ?
O3 C10 C11 C12 -79.4(4) . . . . ?
C3 C4 C5 O1 178.3(3) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
O4 C11 C12 C13 12.1(5) . . . . ?
O4 C11 C12 C17 -169.0(4) . . . . ?
C5 O1 C9 O2 -178.0(3) . . . . ?
C5 O1 C9 C8 2.2(4) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C6 C7 C8 C9 2.0(4) . . . . ?
C6 C7 C8 C10 -178.0(3) . . . . ?
C7 C8 C9 O1 -3.2(4) . . . . ?
C7 C8 C9 O2 177.0(3) . . . . ?
C7 C8 C10 O3 -8.4(5) . . . . ?
C7 C8 C10 C11 166.5(3) . . . . ?
C8 C10 C11 O4 -78.4(4) . . . . ?
C8 C10 C11 C12 105.4(4) . . . . ?
C9 O1 C5 C4 179.9(3) . . . . ?
C9 O1 C5 C6 0.0(4) . . . . ?
C9 C8 C10 O3 171.6(3) . . . . ?
C9 C8 C10 C11 -13.5(4) . . . . ?
C10 C8 C9 O1 176.8(3) . . . . ?
C10 C8 C9 O2 -3.0(5) . . . . ?
C10 C11 C12 C13 -172.1(3) . . . . ?
C10 C11 C12 C17 6.8(5) . . . . ?
C11 C12 C13 C14 178.2(4) . . . . ?
C11 C12 C17 C16 -178.7(4) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C12 C17 C16 0.2(6) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C12 0.3(7) . . . . ?
C17 C12 C13 C14 -0.7(5) . . . . ?

_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.609
####################################################################### 
# 
# 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_202009191
_database_code_depnum_ccdc_archive 'CCDC 2036909'
loop_
_audit_author_name
_audit_author_address
'Xi Jinhu'
;Zhengzhou university
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-25
_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 O4'
_chemical_formula_sum            'C24 H16 O4'
_chemical_formula_weight         368.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H30O2N2
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   19.224(2)
_cell_length_b                   20.020(2)
_cell_length_c                   10.0058(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.418(10)
_cell_angle_gamma                90
_cell_volume                     3818.6(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0140
_cell_measurement_theta_min      4.4200
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88835
_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    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15425
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.150
_diffrn_reflns_theta_max         67.150
_diffrn_reflns_theta_min         4.417
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -69.00   1.00    4.50    --  -33.50 178.00 -60.00   38
  2  ω   -102.00 -16.00   1.00    4.50    --  -33.50 -57.00 -90.00   86
  3  ω    -45.00  33.00   1.00    4.50    --  -33.50  57.00  60.00   78
  4  ω     49.00  74.00   1.00    4.50    --   36.47 -99.00   0.00   25
  5  ω     -4.00  31.00   1.00    4.50    --   36.47 -99.00   0.00   35
  6  ω     48.00  74.00   1.00    4.50    --   36.47 -99.00-150.00   26
  7  ω     70.00 110.00   1.00    4.50    --   36.47 178.00-120.00   40
  8  ω    -20.00  10.00   1.00    4.50    --   36.47 -77.00-180.00   30
  9  ω     40.00  65.00   1.00    4.50    --   36.47 -77.00-180.00   25
 10  ω     48.00  97.00   1.00    4.50    --   36.47  57.00-150.00   49
 11  ω     23.00  51.00   1.00    4.50    --   36.47  37.00-180.00   28
 12  ω     42.00 123.00   1.00   10.50    --  108.00 -61.00 -90.00   81
 13  ω     92.00 175.00   1.00   10.50    --  108.00  61.00  30.00   83
 14  ω     93.00 125.00   1.00   10.50    --  108.00 -61.00  90.00   32
 15  ω     78.00 104.00   1.00   10.50    --  108.00 -94.00-180.00   26
 16  ω     96.00 176.00   1.00   10.50    --  108.00  61.00  60.00   80
 17  ω     38.00  66.00   1.00   10.50    --  108.00 -94.00-180.00   28
 18  ω     57.00 145.00   1.00   10.50    --  108.00 178.00-150.00   88
 19  ω     65.00 112.00   1.00   10.50    --  108.00-111.00   0.00   47
 20  ω    141.00 178.00   1.00   10.50    --  108.00  45.00 -60.00   37
 21  ω    100.00 127.00   1.00   10.50    --  108.00  45.00 -60.00   27
;
_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      -0.0419725000
_diffrn_orient_matrix_UB_12      0.0648233000
_diffrn_orient_matrix_UB_13      0.0132696000
_diffrn_orient_matrix_UB_21      0.0648020000
_diffrn_orient_matrix_UB_22      0.0416723000
_diffrn_orient_matrix_UB_23      -0.0235184000
_diffrn_orient_matrix_UB_31      -0.0240016000
_diffrn_orient_matrix_UB_32      -0.0007717000
_diffrn_orient_matrix_UB_33      -0.1529027000
_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                4196
_reflns_number_total             6779
_reflns_odcompleteness_completeness 99.76
_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         0.200
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00162(15)
_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   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.026
_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)+(0.0740P)²+0.0111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1779
_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), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C6'(H6'), C8'(H8'), C9'(H9'),
  C14'(H14'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'), C20'(H20'),
 C21'(H21'), C22'(H22'), C23'(H23'), C24'(H24')
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10'(H10D,H10E,H10F)
;
_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
O1 O 0.17849(9) 0.61924(9) 0.8573(2) 0.0641(5) Uani 1 1 d . . . . .
O2 O 0.20413(10) 0.72642(10) 0.8669(3) 0.0839(7) Uani 1 1 d . . . . .
O3 O 0.01862(11) 0.79502(11) 0.7501(3) 0.0910(8) Uani 1 1 d . . . . .
O4 O 0.11081(16) 0.80552(13) 1.0435(2) 0.0993(9) Uani 1 1 d . . . . .
C1 C 0.15832(14) 0.68524(14) 0.8550(3) 0.0609(7) Uani 1 1 d . . . . .
C2 C 0.08356(14) 0.69954(14) 0.8350(3) 0.0556(7) Uani 1 1 d . . . . .
C3 C 0.03516(13) 0.64993(14) 0.8108(3) 0.0545(6) Uani 1 1 d . . . . .
C4 C 0.05863(14) 0.58127(13) 0.8105(3) 0.0575(7) Uani 1 1 d . . . . .
C5 C 0.13057(14) 0.56777(13) 0.8314(3) 0.0558(7) Uani 1 1 d . . . . .
C6 C 0.15740(15) 0.50430(14) 0.8265(3) 0.0620(7) Uani 1 1 d . . . . .
H6 H 0.2057 0.4977 0.8424 0.074 Uiso 1 1 calc R . . . .
C7 C 0.11359(17) 0.45044(15) 0.7985(3) 0.0699(8) Uani 1 1 d . . . . .
C8 C 0.04131(17) 0.46228(16) 0.7803(4) 0.0854(11) Uani 1 1 d . . . . .
H8 H 0.0106 0.4265 0.7630 0.102 Uiso 1 1 calc R . . . .
C9 C 0.01487(16) 0.52530(16) 0.7876(4) 0.0784(10) Uani 1 1 d . . . . .
H9 H -0.0335 0.5313 0.7770 0.094 Uiso 1 1 calc R . . . .
C10 C 0.14247(19) 0.38091(16) 0.7845(4) 0.0890(11) Uani 1 1 d . . . . .
H10A H 0.1461 0.3721 0.6914 0.134 Uiso 1 1 calc GR . . . .
H10B H 0.1116 0.3489 0.8172 0.134 Uiso 1 1 calc GR . . . .
H10C H 0.1881 0.3777 0.8361 0.134 Uiso 1 1 calc GR . . . .
C11 C 0.06652(14) 0.77159(15) 0.8263(3) 0.0622(7) Uani 1 1 d . . . . .
C12 C 0.10811(16) 0.81964(15) 0.9241(3) 0.0649(7) Uani 1 1 d . . . . .
C13 C 0.13647(14) 0.88219(14) 0.8749(3) 0.0594(7) Uani 1 1 d . . . . .
C14 C 0.15009(18) 0.93587(16) 0.9613(3) 0.0747(9) Uani 1 1 d . . . . .
H14 H 0.1400 0.9325 1.0494 0.090 Uiso 1 1 calc R . . . .
C15 C 0.1783(2) 0.99410(17) 0.9192(4) 0.0858(11) Uani 1 1 d . . . . .
H15 H 0.1872 1.0299 0.9782 0.103 Uiso 1 1 calc R . . . .
C16 C 0.1933(2) 0.99881(19) 0.7897(4) 0.0959(12) Uani 1 1 d . . . . .
H16 H 0.2117 1.0383 0.7600 0.115 Uiso 1 1 calc R . . . .
C17 C 0.1814(2) 0.9458(2) 0.7034(4) 0.1017(13) Uani 1 1 d . . . . .
H17 H 0.1930 0.9493 0.6163 0.122 Uiso 1 1 calc R . . . .
C18 C 0.15250(18) 0.88725(17) 0.7438(3) 0.0770(9) Uani 1 1 d . . . . .
H18 H 0.1439 0.8517 0.6842 0.092 Uiso 1 1 calc R . . . .
C19 C -0.04166(14) 0.66468(13) 0.7853(3) 0.0571(7) Uani 1 1 d . . . . .
C20 C -0.07697(15) 0.65689(16) 0.6574(3) 0.0698(8) Uani 1 1 d . . . . .
H20 H -0.0531 0.6418 0.5881 0.084 Uiso 1 1 calc R . . . .
C21 C -0.14785(16) 0.67152(16) 0.6316(3) 0.0746(9) Uani 1 1 d . . . . .
H21 H -0.1712 0.6667 0.5447 0.089 Uiso 1 1 calc R . . . .
C22 C -0.18362(16) 0.69290(16) 0.7326(4) 0.0765(9) Uani 1 1 d . . . . .
H22 H -0.2314 0.7020 0.7149 0.092 Uiso 1 1 calc R . . . .
C23 C -0.14937(17) 0.70092(18) 0.8599(4) 0.0852(10) Uani 1 1 d . . . . .
H23 H -0.1737 0.7158 0.9287 0.102 Uiso 1 1 calc R . . . .
C24 C -0.07799(16) 0.68680(17) 0.8868(3) 0.0732(9) Uani 1 1 d . . . . .
H24 H -0.0548 0.6923 0.9735 0.088 Uiso 1 1 calc R . . . .
O1' O 0.32804(10) 0.25693(9) 0.5685(2) 0.0719(6) Uani 1 1 d . . . . .
O2' O 0.30635(12) 0.36405(11) 0.5274(3) 0.0944(9) Uani 1 1 d . . . . .
O3' O 0.48311(10) 0.43597(10) 0.6757(2) 0.0787(7) Uani 1 1 d . . . . .
O4' O 0.33468(13) 0.44308(11) 0.8030(2) 0.0816(7) Uani 1 1 d . . . . .
C1' C 0.34464(15) 0.32332(14) 0.5867(3) 0.0679(8) Uani 1 1 d . . . . .
C2' C 0.40932(14) 0.33969(13) 0.6730(3) 0.0564(7) Uani 1 1 d . . . . .
C3' C 0.45137(13) 0.29162(13) 0.7364(3) 0.0525(6) Uani 1 1 d . . . . .
C4' C 0.43023(13) 0.22235(13) 0.7202(3) 0.0539(6) Uani 1 1 d . . . . .
C5' C 0.36910(14) 0.20706(14) 0.6330(3) 0.0587(7) Uani 1 1 d . . . . .
C6' C 0.34764(15) 0.14239(14) 0.6063(3) 0.0647(7) Uani 1 1 d . . . . .
H6' H 0.3076 0.1340 0.5458 0.078 Uiso 1 1 calc R . . . .
C7' C 0.38535(16) 0.08968(14) 0.6688(3) 0.0641(7) Uani 1 1 d . . . . .
C8' C 0.44514(16) 0.10369(14) 0.7597(3) 0.0653(8) Uani 1 1 d . . . . .
H8' H 0.4706 0.0687 0.8035 0.078 Uiso 1 1 calc R . . . .
C9' C 0.46682(15) 0.16814(14) 0.7853(3) 0.0628(7) Uani 1 1 d . . . . .
H9' H 0.5065 0.1762 0.8469 0.075 Uiso 1 1 calc R . . . .
C10' C 0.3638(2) 0.01809(15) 0.6364(4) 0.0886(11) Uani 1 1 d . . . . .
H10D H 0.4032 -0.0064 0.6120 0.133 Uiso 1 1 calc GR . . . .
H10E H 0.3265 0.0175 0.5627 0.133 Uiso 1 1 calc GR . . . .
H10F H 0.3479 -0.0022 0.7140 0.133 Uiso 1 1 calc GR . . . .
C11' C 0.42548(14) 0.41284(13) 0.6799(3) 0.0575(7) Uani 1 1 d . . . . .
C12' C 0.36616(14) 0.45937(14) 0.7090(3) 0.0579(7) Uani 1 1 d . . . . .
C13' C 0.35449(13) 0.52339(12) 0.6368(3) 0.0525(6) Uani 1 1 d . . . . .
C14' C 0.38119(17) 0.53498(14) 0.5162(3) 0.0664(8) Uani 1 1 d . . . . .
H14' H 0.4089 0.5029 0.4814 0.080 Uiso 1 1 calc R . . . .
C15' C 0.36643(18) 0.59418(15) 0.4484(3) 0.0738(9) Uani 1 1 d . . . . .
H15' H 0.3841 0.6018 0.3675 0.089 Uiso 1 1 calc R . . . .
C16' C 0.32587(17) 0.64229(14) 0.4990(3) 0.0702(8) Uani 1 1 d . . . . .
H16' H 0.3158 0.6819 0.4520 0.084 Uiso 1 1 calc R . . . .
C17' C 0.30038(16) 0.63160(14) 0.6194(3) 0.0696(8) Uani 1 1 d . . . . .
H17' H 0.2736 0.6643 0.6547 0.083 Uiso 1 1 calc R . . . .
C18' C 0.31443(14) 0.57251(13) 0.6876(3) 0.0608(7) Uani 1 1 d . . . . .
H18' H 0.2968 0.5654 0.7687 0.073 Uiso 1 1 calc R . . . .
C19' C 0.51818(13) 0.30826(12) 0.8231(3) 0.0519(6) Uani 1 1 d . . . . .
C20' C 0.58205(14) 0.28704(13) 0.7871(3) 0.0616(7) Uani 1 1 d . . . . .
H20' H 0.5833 0.2615 0.7098 0.074 Uiso 1 1 calc R . . . .
C21' C 0.64386(15) 0.30416(14) 0.8667(3) 0.0712(9) Uani 1 1 d . . . . .
H21' H 0.6867 0.2907 0.8419 0.085 Uiso 1 1 calc R . . . .
C22' C 0.64215(16) 0.34091(15) 0.9821(3) 0.0721(9) Uani 1 1 d . . . . .
H22' H 0.6838 0.3519 1.0356 0.087 Uiso 1 1 calc R . . . .
C23' C 0.57926(17) 0.36140(17) 1.0188(3) 0.0751(9) Uani 1 1 d . . . . .
H23' H 0.5784 0.3860 1.0974 0.090 Uiso 1 1 calc R . . . .
C24' C 0.51715(15) 0.34567(14) 0.9396(3) 0.0649(8) Uani 1 1 d . . . . .
H24' H 0.4747 0.3602 0.9643 0.078 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.376(3) . ?
O1 C5 1.384(3) . ?
O2 C1 1.201(3) . ?
O3 C11 1.212(3) . ?
O4 C12 1.222(3) . ?
C1 C2 1.454(4) . ?
C2 C3 1.361(4) . ?
C2 C11 1.479(4) . ?
C3 C4 1.447(4) . ?
C3 C19 1.495(4) . ?
C4 C5 1.398(4) . ?
C4 C9 1.402(4) . ?
C5 C6 1.375(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(4) . ?
C7 C8 1.398(4) . ?
C7 C10 1.512(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.523(4) . ?
C12 C13 1.475(4) . ?
C13 C14 1.382(4) . ?
C13 C18 1.390(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.368(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 C24 1.378(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.363(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.365(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.393(4) . ?
C24 H24 0.9300 . ?
O1' C1' 1.373(3) . ?
O1' C5' 1.380(3) . ?
O2' C1' 1.203(3) . ?
O3' C11' 1.206(3) . ?
O4' C12' 1.227(3) . ?
C1' C2' 1.456(3) . ?
C2' C3' 1.360(3) . ?
C2' C11' 1.497(4) . ?
C3' C4' 1.448(3) . ?
C3' C19' 1.492(3) . ?
C4' C5' 1.404(3) . ?
C4' C9' 1.407(4) . ?
C5' C6' 1.375(4) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.383(4) . ?
C7' C8' 1.399(4) . ?
C7' C10' 1.516(4) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.370(4) . ?
C9' H9' 0.9300 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11' C12' 1.529(4) . ?
C12' C13' 1.474(4) . ?
C13' C14' 1.391(4) . ?
C13' C18' 1.385(4) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.377(4) . ?
C15' H15' 0.9300 . ?
C15' C16' 1.376(4) . ?
C16' H16' 0.9300 . ?
C16' C17' 1.374(4) . ?
C17' H17' 0.9300 . ?
C17' C18' 1.375(4) . ?
C18' H18' 0.9300 . ?
C19' C20' 1.390(4) . ?
C19' C24' 1.388(4) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.385(4) . ?
C21' H21' 0.9300 . ?
C21' C22' 1.373(5) . ?
C22' H22' 0.9300 . ?
C22' C23' 1.371(5) . ?
C23' H23' 0.9300 . ?
C23' C24' 1.382(4) . ?
C24' H24' 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
C1 O1 C5 122.2(2) . . ?
O1 C1 C2 117.6(2) . . ?
O2 C1 O1 117.1(2) . . ?
O2 C1 C2 125.3(3) . . ?
C1 C2 C11 114.0(2) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 C11 124.1(2) . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 C19 121.6(2) . . ?
C4 C3 C19 119.2(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 C9 115.5(3) . . ?
C9 C4 C3 125.4(3) . . ?
O1 C5 C4 120.4(2) . . ?
C6 C5 O1 116.8(2) . . ?
C6 C5 C4 122.8(2) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 117.8(3) . . ?
C6 C7 C10 121.2(3) . . ?
C8 C7 C10 121.0(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 H9 119.1 . . ?
C8 C9 C4 121.8(3) . . ?
C8 C9 H9 119.1 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C2 124.0(3) . . ?
O3 C11 C12 116.9(3) . . ?
C2 C11 C12 119.0(2) . . ?
O4 C12 C11 115.7(3) . . ?
O4 C12 C13 123.4(3) . . ?
C13 C12 C11 120.5(3) . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 C18 119.1(3) . . ?
C18 C13 C12 120.9(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 120.5 . . ?
C17 C18 C13 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C3 119.5(3) . . ?
C24 C19 C3 121.4(2) . . ?
C24 C19 C20 119.0(3) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 120.2(3) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C1' O1' C5' 121.9(2) . . ?
O1' C1' C2' 117.6(2) . . ?
O2' C1' O1' 118.3(2) . . ?
O2' C1' C2' 124.1(3) . . ?
C1' C2' C11' 113.8(2) . . ?
C3' C2' C1' 121.9(2) . . ?
C3' C2' C11' 124.3(2) . . ?
C2' C3' C4' 118.9(2) . . ?
C2' C3' C19' 121.9(2) . . ?
C4' C3' C19' 119.2(2) . . ?
C5' C4' C3' 118.6(2) . . ?
C5' C4' C9' 116.6(2) . . ?
C9' C4' C3' 124.8(2) . . ?
O1' C5' C4' 121.0(2) . . ?
C6' C5' O1' 116.8(2) . . ?
C6' C5' C4' 122.2(3) . . ?
C5' C6' H6' 119.9 . . ?
C5' C6' C7' 120.3(3) . . ?
C7' C6' H6' 119.9 . . ?
C6' C7' C8' 118.7(3) . . ?
C6' C7' C10' 120.8(3) . . ?
C8' C7' C10' 120.5(3) . . ?
C7' C8' H8' 119.5 . . ?
C9' C8' C7' 121.0(3) . . ?
C9' C8' H8' 119.5 . . ?
C4' C9' H9' 119.4 . . ?
C8' C9' C4' 121.2(3) . . ?
C8' C9' H9' 119.4 . . ?
C7' C10' H10D 109.5 . . ?
C7' C10' H10E 109.5 . . ?
C7' C10' H10F 109.5 . . ?
H10D C10' H10E 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
O3' C11' C2' 124.0(3) . . ?
O3' C11' C12' 118.9(2) . . ?
C2' C11' C12' 116.7(2) . . ?
O4' C12' C11' 116.0(3) . . ?
O4' C12' C13' 123.2(3) . . ?
C13' C12' C11' 120.4(3) . . ?
C14' C13' C12' 121.4(3) . . ?
C18' C13' C12' 119.6(3) . . ?
C18' C13' C14' 119.0(3) . . ?
C13' C14' H14' 120.2 . . ?
C15' C14' C13' 119.7(3) . . ?
C15' C14' H14' 120.2 . . ?
C14' C15' H15' 119.6 . . ?
C16' C15' C14' 120.8(3) . . ?
C16' C15' H15' 119.6 . . ?
C15' C16' H16' 120.1 . . ?
C17' C16' C15' 119.8(3) . . ?
C17' C16' H16' 120.1 . . ?
C16' C17' H17' 120.0 . . ?
C16' C17' C18' 120.0(3) . . ?
C18' C17' H17' 120.0 . . ?
C13' C18' H18' 119.6 . . ?
C17' C18' C13' 120.8(3) . . ?
C17' C18' H18' 119.6 . . ?
C20' C19' C3' 120.3(3) . . ?
C24' C19' C3' 120.3(3) . . ?
C24' C19' C20' 119.4(2) . . ?
C19' C20' H20' 120.1 . . ?
C21' C20' C19' 119.7(3) . . ?
C21' C20' H20' 120.1 . . ?
C20' C21' H21' 119.9 . . ?
C22' C21' C20' 120.3(3) . . ?
C22' C21' H21' 119.9 . . ?
C21' C22' H22' 119.9 . . ?
C23' C22' C21' 120.2(3) . . ?
C23' C22' H22' 119.9 . . ?
C22' C23' H23' 119.8 . . ?
C22' C23' C24' 120.3(3) . . ?
C24' C23' H23' 119.8 . . ?
C19' C24' H24' 120.0 . . ?
C23' C24' C19' 120.0(3) . . ?
C23' C24' H24' 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -4.1(4) . . . . ?
O1 C1 C2 C11 -176.8(2) . . . . ?
O1 C5 C6 C7 -178.6(3) . . . . ?
O2 C1 C2 C3 174.3(3) . . . . ?
O2 C1 C2 C11 1.6(5) . . . . ?
O3 C11 C12 O4 123.3(4) . . . . ?
O3 C11 C12 C13 -50.8(4) . . . . ?
O4 C12 C13 C14 -18.0(5) . . . . ?
O4 C12 C13 C18 159.4(3) . . . . ?
C1 O1 C5 C4 -4.3(4) . . . . ?
C1 O1 C5 C6 175.2(3) . . . . ?
C1 C2 C3 C4 2.6(4) . . . . ?
C1 C2 C3 C19 -177.8(3) . . . . ?
C1 C2 C11 O3 141.5(3) . . . . ?
C1 C2 C11 C12 -42.5(4) . . . . ?
C2 C3 C4 C5 -1.8(4) . . . . ?
C2 C3 C4 C9 179.8(3) . . . . ?
C2 C3 C19 C20 108.3(3) . . . . ?
C2 C3 C19 C24 -70.8(4) . . . . ?
C2 C11 C12 O4 -53.0(4) . . . . ?
C2 C11 C12 C13 132.9(3) . . . . ?
C3 C2 C11 O3 -31.0(5) . . . . ?
C3 C2 C11 C12 145.0(3) . . . . ?
C3 C4 C5 O1 2.6(4) . . . . ?
C3 C4 C5 C6 -176.9(3) . . . . ?
C3 C4 C9 C8 175.7(3) . . . . ?
C3 C19 C20 C21 -178.8(3) . . . . ?
C3 C19 C24 C23 179.2(3) . . . . ?
C4 C3 C19 C20 -72.1(4) . . . . ?
C4 C3 C19 C24 108.8(3) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 O1 C1 O2 -173.6(3) . . . . ?
C5 O1 C1 C2 4.9(4) . . . . ?
C5 C4 C9 C8 -2.8(5) . . . . ?
C5 C6 C7 C8 -2.4(5) . . . . ?
C5 C6 C7 C10 176.3(3) . . . . ?
C6 C7 C8 C9 1.2(6) . . . . ?
C7 C8 C9 C4 1.4(6) . . . . ?
C9 C4 C5 O1 -178.9(3) . . . . ?
C9 C4 C5 C6 1.6(4) . . . . ?
C10 C7 C8 C9 -177.4(4) . . . . ?
C11 C2 C3 C4 174.5(3) . . . . ?
C11 C2 C3 C19 -5.8(4) . . . . ?
C11 C12 C13 C14 155.7(3) . . . . ?
C11 C12 C13 C18 -26.9(4) . . . . ?
C12 C13 C14 C15 178.2(3) . . . . ?
C12 C13 C18 C17 -177.6(3) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C13 C18 C17 -0.2(5) . . . . ?
C14 C15 C16 C17 -1.1(6) . . . . ?
C15 C16 C17 C18 1.7(7) . . . . ?
C16 C17 C18 C13 -1.0(6) . . . . ?
C18 C13 C14 C15 0.7(5) . . . . ?
C19 C3 C4 C5 178.6(3) . . . . ?
C19 C3 C4 C9 0.2(5) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C20 C19 C24 C23 0.1(5) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C21 C22 C23 C24 -0.5(6) . . . . ?
C22 C23 C24 C19 0.0(6) . . . . ?
C24 C19 C20 C21 0.4(5) . . . . ?
O1' C1' C2' C3' -1.6(5) . . . . ?
O1' C1' C2' C11' 176.2(3) . . . . ?
O1' C5' C6' C7' -178.9(3) . . . . ?
O2' C1' C2' C3' -179.0(3) . . . . ?
O2' C1' C2' C11' -1.2(5) . . . . ?
O3' C11' C12' O4' -126.1(3) . . . . ?
O3' C11' C12' C13' 47.1(4) . . . . ?
O4' C12' C13' C14' -168.0(3) . . . . ?
O4' C12' C13' C18' 10.1(4) . . . . ?
C1' O1' C5' C4' -0.4(5) . . . . ?
C1' O1' C5' C6' -179.5(3) . . . . ?
C1' C2' C3' C4' -1.5(5) . . . . ?
C1' C2' C3' C19' 179.1(3) . . . . ?
C1' C2' C11' O3' -137.3(3) . . . . ?
C1' C2' C11' C12' 49.4(4) . . . . ?
C2' C3' C4' C5' 3.7(4) . . . . ?
C2' C3' C4' C9' -176.6(3) . . . . ?
C2' C3' C19' C20' -115.9(3) . . . . ?
C2' C3' C19' C24' 63.4(4) . . . . ?
C2' C11' C12' O4' 47.6(3) . . . . ?
C2' C11' C12' C13' -139.2(2) . . . . ?
C3' C2' C11' O3' 40.5(5) . . . . ?
C3' C2' C11' C12' -132.9(3) . . . . ?
C3' C4' C5' O1' -2.9(4) . . . . ?
C3' C4' C5' C6' 176.3(3) . . . . ?
C3' C4' C9' C8' -176.9(3) . . . . ?
C3' C19' C20' C21' 178.5(2) . . . . ?
C3' C19' C24' C23' -179.4(3) . . . . ?
C4' C3' C19' C20' 64.7(4) . . . . ?
C4' C3' C19' C24' -116.0(3) . . . . ?
C4' C5' C6' C7' 2.0(5) . . . . ?
C5' O1' C1' O2' -179.8(3) . . . . ?
C5' O1' C1' C2' 2.6(5) . . . . ?
C5' C4' C9' C8' 2.8(5) . . . . ?
C5' C6' C7' C8' 0.3(5) . . . . ?
C5' C6' C7' C10' -177.8(3) . . . . ?
C6' C7' C8' C9' -0.9(5) . . . . ?
C7' C8' C9' C4' -0.7(5) . . . . ?
C9' C4' C5' O1' 177.5(3) . . . . ?
C9' C4' C5' C6' -3.4(5) . . . . ?
C10' C7' C8' C9' 177.1(3) . . . . ?
C11' C2' C3' C4' -179.2(3) . . . . ?
C11' C2' C3' C19' 1.4(5) . . . . ?
C11' C12' C13' C14' 19.3(4) . . . . ?
C11' C12' C13' C18' -162.6(2) . . . . ?
C12' C13' C14' C15' 176.9(3) . . . . ?
C12' C13' C18' C17' -177.3(2) . . . . ?
C13' C14' C15' C16' 0.4(5) . . . . ?
C14' C13' C18' C17' 0.8(4) . . . . ?
C14' C15' C16' C17' 0.7(5) . . . . ?
C15' C16' C17' C18' -1.1(5) . . . . ?
C16' C17' C18' C13' 0.4(4) . . . . ?
C18' C13' C14' C15' -1.2(4) . . . . ?
C19' C3' C4' C5' -176.8(3) . . . . ?
C19' C3' C4' C9' 2.8(4) . . . . ?
C19' C20' C21' C22' 1.2(4) . . . . ?
C20' C19' C24' C23' -0.1(4) . . . . ?
C20' C21' C22' C23' -0.6(5) . . . . ?
C21' C22' C23' C24' -0.4(5) . . . . ?
C22' C23' C24' C19' 0.8(5) . . . . ?
C24' C19' C20' C21' -0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.856
_oxdiff_exptl_absorpt_empirical_full_min 0.788
