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

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

data_202011247
_database_code_depnum_ccdc_archive 'CCDC 2074877'
loop_
_audit_author_name
_audit_author_address
ywp
;Zhengzhou university
China
;
_audit_update_record             
;
2021-04-01 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_audit_creation_date             2020-11-16
_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 H19 N O4'
_chemical_formula_sum            'C25 H19 N O4'
_chemical_formula_weight         397.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N1
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.3096(18)
_cell_length_b                   10.340(3)
_cell_length_c                   10.3533(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.294(17)
_cell_angle_gamma                90
_cell_volume                     996.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1940
_cell_measurement_theta_min      4.2590
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76652
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.15
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7900
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.271
_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    -59.00  38.00   1.00    1.00    --  -33.50  19.00   0.00   97
  2  ω   -104.00 -71.00   1.00    1.00    --  -33.50   0.00 150.00   33
  3  ω    -43.00  -8.00   1.00    1.00    --  -33.50   0.00 150.00   35
  4  ω     34.00  69.00   1.00    1.00    --   36.47  77.00 120.00   35
  5  ω     11.00 102.00   1.00    1.00    --   36.47  77.00-120.00   91
  6  ω     33.00  59.00   1.00    1.00    --   36.47  77.00-150.00   26
  7  ω    -34.00   3.00   1.00    1.00    --   36.47   0.00  90.00   37
  8  ω      1.00  26.00   1.00    1.00    --   36.47 -99.00 -90.00   25
  9  ω     32.00  71.00   1.00    1.00    --   36.47  77.00 -60.00   39
 10  ω     34.00 108.00   1.00    1.00    --   36.47   0.00  90.00   74
 11  ω     21.00  47.00   1.00    1.00    --   36.47  19.00   0.00   26
 12  ω     65.00 106.00   1.00    1.00    --   36.47 178.00 -60.00   41
 13  ω     70.00 109.00   1.00    1.00    --   36.47 178.00  30.00   39
 14  ω     17.00  54.00   1.00    1.00    --   36.47  37.00 -90.00   37
 15  ω     -9.00  16.00   1.00    1.00    --   36.47 108.00 161.25   25
 16  ω      8.00  44.00   1.00    1.00    --   36.47  19.00 -90.00   36
 17  ω     51.00  77.00   1.00    1.00    --   36.47 -99.00 -90.00   26
 18  ω    142.00 168.00   1.00    3.00    --  108.00  77.00 -90.00   26
 19  ω     79.00 105.00   1.00    3.00    --  108.00  77.00 -90.00   26
 20  ω     79.00 105.00   1.00    3.00    --  108.00  77.00-120.00   26
 21  ω     83.00 109.00   1.00    3.00    --  108.00  30.00 -60.00   26
 22  ω    139.00 177.00   1.00    3.00    --  108.00 111.00 120.00   38
 23  ω     87.00 113.00   1.00    3.00    --  108.00  30.00-120.00   26
 24  ω     79.00 106.00   1.00    3.00    --  108.00-111.00 -90.00   27
 25  ω     43.00  69.00   1.00    3.00    --  108.00 -77.00-120.00   26
 26  ω    146.00 175.00   1.00    3.00    --  108.00  30.00 -90.00   29
 27  ω     87.00 114.00   1.00    3.00    --  108.00  30.00-180.00   27
 28  ω     82.00 114.00   1.00    3.00    --  108.00  30.00 -90.00   32
 29  ω     37.00  69.00   1.00    3.00    --  108.00-111.00 -90.00   32
 30  ω     84.00 109.00   1.00    3.00    --  108.00  30.00-150.00   25
 31  ω     88.00 115.00   1.00    3.00    --  108.00  61.00 -60.00   27
 32  ω     80.00 106.00   1.00    3.00    --  108.00-111.00   0.00   26
 33  ω     91.00 123.00   1.00    3.00    --  108.00  45.00 150.00   32
 34  ω    126.00 177.00   1.00    3.00    --  108.00  77.00-180.00   51
 35  ω     45.00 108.00   1.00    3.00    --  108.00 -61.00-120.00   63
 36  ω     80.00 175.00   1.00    3.00    --  108.00  77.00 150.00   95
 37  ω     88.00 115.00   1.00    3.00    --  108.00  61.00 -90.00   27
 38  ω     89.00 115.00   1.00    3.00    --  108.00  61.00-150.00   26
 39  ω     88.00 114.00   1.00    3.00    --  108.00  61.00-180.00   26
 40  ω     82.00 114.00   1.00    3.00    --  108.00  30.00 -30.00   32
 41  ω    117.00 176.00   1.00    3.00    --  108.00  77.00-150.00   59
 42  ω     82.00 108.00   1.00    3.00    --  108.00  77.00 120.00   26
 43  ω    110.00 160.00   1.00    3.00    --  108.00  77.00 120.00   50
 44  ω     88.00 114.00   1.00    3.00    --  108.00  61.00-120.00   26
 45  ω     89.00 114.00   1.00    3.00    --  108.00  45.00 -90.00   25
 46  ω     79.00 105.00   1.00    3.00    --  108.00  77.00 -60.00   26
 47  ω     79.00 105.00   1.00    3.00    --  108.00  77.00-150.00   26
 48  ω    111.00 176.00   1.00    3.00    --  108.00  77.00-120.00   65
 49  ω     65.00  90.00   1.00    3.00    --  108.00  15.00 -90.00   25
 50  ω     80.00 109.00   1.00    3.00    --  108.00  77.00-180.00   29
;
_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      -0.0871142000
_diffrn_orient_matrix_UB_12      -0.0197345000
_diffrn_orient_matrix_UB_13      -0.1271027000
_diffrn_orient_matrix_UB_21      -0.1364958000
_diffrn_orient_matrix_UB_22      -0.0241750000
_diffrn_orient_matrix_UB_23      0.0774618000
_diffrn_orient_matrix_UB_31      -0.0343880000
_diffrn_orient_matrix_UB_32      0.1456470000
_diffrn_orient_matrix_UB_33      -0.0044858000
_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         0.704
_reflns_Friedel_fraction_full    0.795
_reflns_Friedel_fraction_max     0.795
_reflns_number_gt                2641
_reflns_number_total             3218
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.110
_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)+(0.0453P)²+0.0274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1220
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_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 0.5528(4) 0.4751(5) -0.0344(4) 0.0518(10) Uani 1 1 d . . . . .
C2 C 0.4297(4) 0.3789(4) -0.0534(4) 0.0493(10) Uani 1 1 d . . . . .
H2 H 0.4698 0.2964 -0.0821 0.059 Uiso 1 1 calc R . . . .
C3 C 0.3693(4) 0.3601(4) 0.0851(4) 0.0477(9) Uani 1 1 d . . . . .
H3 H 0.3559 0.2674 0.1004 0.057 Uiso 1 1 calc R . . . .
C4 C 0.4960(4) 0.4089(4) 0.1729(4) 0.0461(9) Uani 1 1 d . . . . .
C5 C 0.5992(4) 0.2952(4) 0.2112(4) 0.0475(9) Uani 1 1 d . . . . .
C6 C 0.6258(4) 0.3008(4) 0.3503(4) 0.0490(9) Uani 1 1 d . . . . .
C7 C 0.5496(4) 0.4036(4) 0.4022(4) 0.0511(10) Uani 1 1 d . . . . .
C8 C 0.4645(4) 0.4780(5) 0.3006(4) 0.0527(10) Uani 1 1 d . . . . .
H8A H 0.4955 0.5675 0.2977 0.063 Uiso 1 1 calc R . . . .
H8B H 0.3627 0.4756 0.3181 0.063 Uiso 1 1 calc R . . . .
C9 C 0.7141(5) 0.2224(5) 0.4288(5) 0.0597(11) Uani 1 1 d . . . . .
H9 H 0.7655 0.1547 0.3930 0.072 Uiso 1 1 calc R . . . .
C10 C 0.7239(5) 0.2463(5) 0.5585(5) 0.0668(13) Uani 1 1 d . . . . .
H10 H 0.7823 0.1950 0.6115 0.080 Uiso 1 1 calc R . . . .
C11 C 0.6459(5) 0.3481(6) 0.6112(4) 0.0680(14) Uani 1 1 d . . . . .
H11 H 0.6524 0.3631 0.6997 0.082 Uiso 1 1 calc R . . . .
C12 C 0.5590(5) 0.4273(5) 0.5347(4) 0.0635(13) Uani 1 1 d . . . . .
H12 H 0.5079 0.4949 0.5711 0.076 Uiso 1 1 calc R . . . .
C13 C 0.2259(4) 0.4281(4) 0.1008(3) 0.0478(9) Uani 1 1 d . . . . .
C14 C 0.1017(5) 0.3541(6) 0.0990(4) 0.0598(11) Uani 1 1 d . . . . .
H14 H 0.1083 0.2646 0.0926 0.072 Uiso 1 1 calc R . . . .
C15 C -0.0323(5) 0.4118(7) 0.1068(5) 0.0746(16) Uani 1 1 d . . . . .
H15 H -0.1145 0.3607 0.1044 0.089 Uiso 1 1 calc R . . . .
C16 C -0.0449(5) 0.5431(7) 0.1180(5) 0.0794(18) Uani 1 1 d . . . . .
H16 H -0.1349 0.5813 0.1237 0.095 Uiso 1 1 calc R . . . .
C17 C 0.0776(5) 0.6180(6) 0.1208(5) 0.0693(14) Uani 1 1 d . . . . .
H17 H 0.0699 0.7072 0.1298 0.083 Uiso 1 1 calc R . . . .
C18 C 0.2125(5) 0.5619(5) 0.1104(4) 0.0557(10) Uani 1 1 d . . . . .
H18 H 0.2941 0.6138 0.1098 0.067 Uiso 1 1 calc R . . . .
C19 C 0.2696(5) 0.3452(4) -0.2429(4) 0.0521(10) Uani 1 1 d . . . . .
C20 C 0.1542(5) 0.4052(4) -0.3256(4) 0.0546(10) Uani 1 1 d . . . . .
C21 C 0.1502(5) 0.3787(5) -0.4576(4) 0.0641(12) Uani 1 1 d . . . . .
H21 H 0.2160 0.3213 -0.4920 0.077 Uiso 1 1 calc R . . . .
C22 C 0.0483(6) 0.4376(6) -0.5380(5) 0.0756(15) Uani 1 1 d . . . . .
H22 H 0.0483 0.4212 -0.6263 0.091 Uiso 1 1 calc R . . . .
C23 C -0.0523(6) 0.5198(6) -0.4886(5) 0.0798(16) Uani 1 1 d . . . . .
H23 H -0.1199 0.5592 -0.5431 0.096 Uiso 1 1 calc R . . . .
C24 C -0.0526(6) 0.5434(6) -0.3582(6) 0.0793(16) Uani 1 1 d . . . . .
H24 H -0.1219 0.5977 -0.3243 0.095 Uiso 1 1 calc R . . . .
C25 C 0.0502(5) 0.4866(5) -0.2759(4) 0.0634(11) Uani 1 1 d . . . . .
H25 H 0.0492 0.5033 -0.1877 0.076 Uiso 1 1 calc R . . . .
N1 N 0.3287(4) 0.4241(4) -0.1511(3) 0.0534(8) Uani 1 1 d . . . . .
H1 H 0.308(4) 0.506(5) -0.145(4) 0.043(11) Uiso 1 1 d . . . . .
O1 O 0.5804(3) 0.4948(3) 0.0927(3) 0.0531(7) Uani 1 1 d . . . . .
O2 O 0.6182(4) 0.5299(4) -0.1156(3) 0.0712(10) Uani 1 1 d . . . . .
O3 O 0.6482(3) 0.2225(3) 0.1323(3) 0.0581(8) Uani 1 1 d . . . . .
O4 O 0.3106(4) 0.2340(4) -0.2587(4) 0.0766(10) 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 1.526(6) . ?
C1 O1 1.350(5) . ?
C1 O2 1.193(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.565(5) . ?
C2 N1 1.443(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.557(5) . ?
C3 C13 1.521(5) . ?
C4 C5 1.564(6) . ?
C4 C8 1.537(5) . ?
C4 O1 1.458(5) . ?
C5 C6 1.457(6) . ?
C5 O3 1.207(5) . ?
C6 C7 1.393(6) . ?
C6 C9 1.401(6) . ?
C7 C8 1.513(6) . ?
C7 C12 1.394(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.367(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(6) . ?
C13 C18 1.392(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.494(6) . ?
C19 N1 1.360(6) . ?
C19 O4 1.223(6) . ?
C20 C21 1.393(6) . ?
C20 C25 1.390(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.389(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.372(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.396(7) . ?
C25 H25 0.9300 . ?
N1 H1 0.87(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 110.5(3) . . ?
O2 C1 C2 127.7(4) . . ?
O2 C1 O1 121.8(4) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 104.3(3) . . ?
C3 C2 H2 108.5 . . ?
N1 C2 C1 110.8(4) . . ?
N1 C2 H2 108.5 . . ?
N1 C2 C3 116.1(3) . . ?
C2 C3 H3 108.6 . . ?
C4 C3 C2 102.2(3) . . ?
C4 C3 H3 108.6 . . ?
C13 C3 C2 112.0(3) . . ?
C13 C3 H3 108.6 . . ?
C13 C3 C4 116.3(3) . . ?
C3 C4 C5 111.0(4) . . ?
C8 C4 C3 119.8(3) . . ?
C8 C4 C5 105.1(3) . . ?
O1 C4 C3 106.0(3) . . ?
O1 C4 C5 105.4(3) . . ?
O1 C4 C8 108.8(3) . . ?
C6 C5 C4 108.1(3) . . ?
O3 C5 C4 122.4(4) . . ?
O3 C5 C6 129.4(4) . . ?
C7 C6 C5 109.6(4) . . ?
C7 C6 C9 121.0(4) . . ?
C9 C6 C5 129.4(4) . . ?
C6 C7 C8 112.5(4) . . ?
C6 C7 C12 119.5(4) . . ?
C12 C7 C8 128.0(4) . . ?
C4 C8 H8A 110.8 . . ?
C4 C8 H8B 110.8 . . ?
C7 C8 C4 104.8(3) . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C6 C9 H9 120.3 . . ?
C10 C9 C6 119.4(5) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(5) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.6(4) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 H12 120.6 . . ?
C11 C12 C7 118.7(5) . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C3 118.5(4) . . ?
C14 C13 C18 118.3(4) . . ?
C18 C13 C3 123.1(4) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.9(5) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(5) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(6) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(5) . . ?
C17 C18 H18 119.9 . . ?
N1 C19 C20 115.2(4) . . ?
O4 C19 C20 122.4(4) . . ?
O4 C19 N1 122.4(4) . . ?
C21 C20 C19 118.9(4) . . ?
C25 C20 C19 122.5(4) . . ?
C25 C20 C21 118.6(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.3(5) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(5) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(5) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(5) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 120.2(5) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C2 N1 H1 114(3) . . ?
C19 N1 C2 122.8(4) . . ?
C19 N1 H1 123(3) . . ?
C1 O1 C4 111.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O2 0.98 2.47 3.431(6) 165.8 2_645
N1 H1 O3 0.87(5) 2.28(5) 3.099(6) 157(4) 2_655

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 -19.1(4) . . . . ?
C1 C2 C3 C13 106.2(4) . . . . ?
C1 C2 N1 C19 137.6(4) . . . . ?
C2 C1 O1 C4 6.1(4) . . . . ?
C2 C3 C4 C5 -91.1(4) . . . . ?
C2 C3 C4 C8 146.2(4) . . . . ?
C2 C3 C4 O1 22.8(4) . . . . ?
C2 C3 C13 C14 103.8(4) . . . . ?
C2 C3 C13 C18 -72.9(5) . . . . ?
C3 C2 N1 C19 -103.7(5) . . . . ?
C3 C4 C5 C6 -131.5(3) . . . . ?
C3 C4 C5 O3 51.0(5) . . . . ?
C3 C4 C8 C7 126.0(4) . . . . ?
C3 C4 O1 C1 -18.9(4) . . . . ?
C3 C13 C14 C15 -176.9(4) . . . . ?
C3 C13 C18 C17 178.1(4) . . . . ?
C4 C3 C13 C14 -139.1(4) . . . . ?
C4 C3 C13 C18 44.2(5) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C5 C6 C9 -177.9(4) . . . . ?
C5 C4 C8 C7 0.4(4) . . . . ?
C5 C4 O1 C1 98.8(4) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C5 C6 C7 C12 179.9(4) . . . . ?
C5 C6 C9 C10 179.3(4) . . . . ?
C6 C7 C8 C4 0.0(5) . . . . ?
C6 C7 C12 C11 0.7(7) . . . . ?
C6 C9 C10 C11 0.1(7) . . . . ?
C7 C6 C9 C10 0.9(7) . . . . ?
C8 C4 C5 C6 -0.7(4) . . . . ?
C8 C4 C5 O3 -178.2(4) . . . . ?
C8 C4 O1 C1 -148.9(3) . . . . ?
C8 C7 C12 C11 -178.8(4) . . . . ?
C9 C6 C7 C8 178.3(4) . . . . ?
C9 C6 C7 C12 -1.3(6) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C10 C11 C12 C7 0.3(7) . . . . ?
C12 C7 C8 C4 179.6(4) . . . . ?
C13 C3 C4 C5 146.5(3) . . . . ?
C13 C3 C4 C8 23.8(6) . . . . ?
C13 C3 C4 O1 -99.5(4) . . . . ?
C13 C14 C15 C16 -0.8(7) . . . . ?
C14 C13 C18 C17 1.5(6) . . . . ?
C14 C15 C16 C17 0.3(8) . . . . ?
C15 C16 C17 C18 1.0(7) . . . . ?
C16 C17 C18 C13 -1.9(7) . . . . ?
C18 C13 C14 C15 -0.1(6) . . . . ?
C19 C20 C21 C22 -177.1(4) . . . . ?
C19 C20 C25 C24 178.0(5) . . . . ?
C20 C19 N1 C2 172.9(4) . . . . ?
C20 C21 C22 C23 -1.9(8) . . . . ?
C21 C20 C25 C24 -2.1(7) . . . . ?
C21 C22 C23 C24 -0.3(8) . . . . ?
C22 C23 C24 C25 1.3(9) . . . . ?
C23 C24 C25 C20 0.0(9) . . . . ?
C25 C20 C21 C22 3.0(7) . . . . ?
N1 C2 C3 C4 -141.2(4) . . . . ?
N1 C2 C3 C13 -16.0(5) . . . . ?
N1 C19 C20 C21 139.1(4) . . . . ?
N1 C19 C20 C25 -40.9(6) . . . . ?
O1 C1 C2 C3 9.1(4) . . . . ?
O1 C1 C2 N1 134.7(3) . . . . ?
O1 C4 C5 C6 114.2(3) . . . . ?
O1 C4 C5 O3 -63.3(5) . . . . ?
O1 C4 C8 C7 -112.1(4) . . . . ?
O2 C1 C2 C3 -169.8(4) . . . . ?
O2 C1 C2 N1 -44.2(6) . . . . ?
O2 C1 O1 C4 -174.9(4) . . . . ?
O3 C5 C6 C7 177.9(4) . . . . ?
O3 C5 C6 C9 -0.7(8) . . . . ?
O4 C19 C20 C21 -39.0(6) . . . . ?
O4 C19 C20 C25 140.9(5) . . . . ?
O4 C19 N1 C2 -9.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.229
_oxdiff_exptl_absorpt_empirical_full_min 0.818
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202106190
_database_code_depnum_ccdc_archive 'CCDC 2097633'
loop_
_audit_author_name
_audit_author_address
ywp
;Zhengzhou University
China
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 F N O5'
_chemical_formula_weight         431.40

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9904(8)
_cell_length_b                   9.9960(6)
_cell_length_c                   10.8047(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.900(8)
_cell_angle_gamma                90
_cell_volume                     1042.72(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.854
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7759
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.234
_diffrn_reflns_theta_max         70.764
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3908
_reflns_number_gt                3380
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.991

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3908
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3171(3) 0.0432(3) 0.0279(3) 0.1004(10) Uani 1 1 d . . . . .
O1 O 0.2399(3) 0.3534(2) 0.3252(2) 0.0566(6) Uani 1 1 d . . . . .
O2 O 0.4287(3) 0.6506(3) 0.1755(3) 0.0737(8) Uani 1 1 d . . . . .
O3 O 0.3661(2) 0.6947(3) 0.3995(2) 0.0580(6) Uani 1 1 d . . . . .
O4 O 0.3643(3) 0.9178(3) 0.4022(4) 0.0877(10) Uani 1 1 d . . . . .
O5 O 0.0199(3) 0.9406(3) 0.0341(2) 0.0761(8) Uani 1 1 d . . . . .
N1 N 0.0835(3) 0.8953(3) 0.2468(3) 0.0524(7) Uani 1 1 d . . . . .
C1 C 0.3952(4) 0.3923(4) 0.0538(3) 0.0542(8) Uani 1 1 d . . . . .
H1A H 0.4350 0.4576 0.0133 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3801(4) 0.2650(4) 0.0058(4) 0.0649(10) Uani 1 1 d . . . . .
H2 H 0.4070 0.2429 -0.0679 0.078 Uiso 1 1 calc R U . . .
C3 C 0.3238(4) 0.1708(4) 0.0704(4) 0.0664(10) Uani 1 1 d . . . . .
C4 C 0.2779(4) 0.1971(4) 0.1766(4) 0.0620(9) Uani 1 1 d . . . . .
H4 H 0.2398 0.1304 0.2169 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2904(3) 0.3274(3) 0.2218(3) 0.0487(7) Uani 1 1 d . . . . .
C6 C 0.3514(3) 0.4257(3) 0.1632(3) 0.0443(7) Uani 1 1 d . . . . .
C7 C 0.3667(3) 0.5618(3) 0.2137(3) 0.0477(7) Uani 1 1 d . . . . .
C8 C 0.2923(3) 0.5893(3) 0.3185(3) 0.0446(7) Uani 1 1 d . . . . .
C9 C 0.2979(4) 0.4658(3) 0.4005(3) 0.0529(8) Uani 1 1 d . . . . .
H9A H 0.3934 0.4467 0.4447 0.064 Uiso 1 1 calc R U . . .
H9B H 0.2473 0.4822 0.4645 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3147(4) 0.8159(4) 0.3544(4) 0.0590(9) Uani 1 1 d . . . . .
C11 C 0.1882(3) 0.7977(3) 0.2438(3) 0.0496(7) Uani 1 1 d . . . . .
H11 H 0.2158 0.8086 0.1636 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1468(3) 0.6489(3) 0.2553(3) 0.0419(6) Uani 1 1 d . . . . .
H12 H 0.1116 0.6108 0.1695 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0389(3) 0.6333(3) 0.3301(3) 0.0457(7) Uani 1 1 d . . . . .
C14 C 0.0554(4) 0.6880(4) 0.4515(3) 0.0565(8) Uani 1 1 d . . . . .
H14 H 0.1388 0.7284 0.4926 0.068 Uiso 1 1 calc R U . . .
C15 C -0.0512(5) 0.6828(4) 0.5119(4) 0.0690(11) Uani 1 1 d . . . . .
H15 H -0.0390 0.7194 0.5931 0.083 Uiso 1 1 calc R U . . .
C16 C -0.1747(5) 0.6238(5) 0.4519(5) 0.0849(14) Uani 1 1 d . . . . .
H16 H -0.2467 0.6214 0.4919 0.102 Uiso 1 1 calc R U . . .
C17 C -0.1918(5) 0.5680(6) 0.3323(6) 0.0913(16) Uani 1 1 d . . . . .
H17 H -0.2748 0.5261 0.2923 0.110 Uiso 1 1 calc R U . . .
C18 C -0.0851(4) 0.5740(4) 0.2712(4) 0.0680(10) Uani 1 1 d . . . . .
H18 H -0.0980 0.5376 0.1898 0.082 Uiso 1 1 calc R U . . .
C19 C 0.0004(4) 0.9527(3) 0.1410(3) 0.0497(7) Uani 1 1 d . . . . .
C20 C -0.1130(4) 1.0362(3) 0.1677(3) 0.0483(7) Uani 1 1 d . . . . .
C21 C -0.1343(4) 1.1643(4) 0.1181(3) 0.0609(9) Uani 1 1 d . . . . .
H21 H -0.0797 1.1975 0.0671 0.073 Uiso 1 1 calc R U . . .
C22 C -0.2374(5) 1.2427(4) 0.1450(4) 0.0778(13) Uani 1 1 d . . . . .
H22 H -0.2507 1.3296 0.1134 0.093 Uiso 1 1 calc R U . . .
C23 C -0.3205(5) 1.1931(5) 0.2183(4) 0.0772(13) Uani 1 1 d . . . . .
H23 H -0.3888 1.2469 0.2367 0.093 Uiso 1 1 calc R U . . .
C24 C -0.3024(4) 1.0646(5) 0.2639(4) 0.0704(11) Uani 1 1 d . . . . .
H24 H -0.3605 1.0301 0.3109 0.084 Uiso 1 1 calc R U . . .
C25 C -0.1977(4) 0.9865(4) 0.2401(3) 0.0564(8) Uani 1 1 d . . . . .
H25 H -0.1840 0.9001 0.2729 0.068 Uiso 1 1 calc R U . . .
H1 H 0.065(4) 0.917(4) 0.322(4) 0.065(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.351(5) . ?
O1 C5 1.364(4) . ?
O1 C9 1.420(4) . ?
O2 C7 1.214(4) . ?
O3 C10 1.357(5) . ?
O3 C8 1.445(4) . ?
O4 C10 1.191(5) . ?
O5 C19 1.226(4) . ?
N1 C19 1.356(4) . ?
N1 C11 1.437(4) . ?
N1 H1 0.91(4) . ?
C1 C2 1.367(6) . ?
C1 C6 1.402(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(6) . ?
C4 C5 1.385(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C6 C7 1.459(5) . ?
C7 C8 1.531(4) . ?
C8 C9 1.512(4) . ?
C8 C12 1.557(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.510(5) . ?
C11 C12 1.558(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.512(4) . ?
C12 H12 0.9800 . ?
C13 C18 1.373(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.495(5) . ?
C20 C21 1.383(5) . ?
C20 C25 1.384(5) . ?
C21 C22 1.383(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(5) . ?
C24 H24 0.9300 . ?
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
C5 O1 C9 115.9(3) . . ?
C10 O3 C8 110.3(3) . . ?
C19 N1 C11 124.0(3) . . ?
C19 N1 H1 116(3) . . ?
C11 N1 H1 120(3) . . ?
C2 C1 C6 120.9(4) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 C3 117.7(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
F1 C3 C4 118.0(4) . . ?
F1 C3 C2 117.7(4) . . ?
C4 C3 C2 124.3(4) . . ?
C3 C4 C5 117.3(4) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
O1 C5 C4 116.7(3) . . ?
O1 C5 C6 122.4(3) . . ?
C4 C5 C6 120.9(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 120.8(3) . . ?
O2 C7 C6 124.6(3) . . ?
O2 C7 C8 120.5(3) . . ?
C6 C7 C8 114.8(3) . . ?
O3 C8 C9 107.7(3) . . ?
O3 C8 C7 108.0(3) . . ?
C9 C8 C7 109.6(3) . . ?
O3 C8 C12 105.1(2) . . ?
C9 C8 C12 117.3(3) . . ?
C7 C8 C12 108.7(3) . . ?
O1 C9 C8 111.2(3) . . ?
O1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O4 C10 O3 122.0(4) . . ?
O4 C10 C11 128.1(4) . . ?
O3 C10 C11 109.8(3) . . ?
N1 C11 C10 111.5(3) . . ?
N1 C11 C12 115.9(3) . . ?
C10 C11 C12 103.7(3) . . ?
N1 C11 H11 108.5 . . ?
C10 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C13 C12 C8 116.1(2) . . ?
C13 C12 C11 112.4(2) . . ?
C8 C12 C11 99.4(2) . . ?
C13 C12 H12 109.5 . . ?
C8 C12 H12 109.5 . . ?
C11 C12 H12 109.5 . . ?
C18 C13 C14 118.7(3) . . ?
C18 C13 C12 118.6(3) . . ?
C14 C13 C12 122.4(3) . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.1(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.6(4) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
O5 C19 N1 122.8(3) . . ?
O5 C19 C20 123.3(3) . . ?
N1 C19 C20 113.8(3) . . ?
C21 C20 C25 119.7(3) . . ?
C21 C20 C19 119.4(3) . . ?
C25 C20 C19 120.8(3) . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.0(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.9(4) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C20 120.3(4) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?

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
C6 C1 C2 C3 -1.5(6) . . . . ?
C1 C2 C3 F1 -175.8(4) . . . . ?
C1 C2 C3 C4 2.2(6) . . . . ?
F1 C3 C4 C5 177.5(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C9 O1 C5 C4 156.3(3) . . . . ?
C9 O1 C5 C6 -23.9(4) . . . . ?
C3 C4 C5 O1 177.8(3) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
O1 C5 C6 C1 -177.1(3) . . . . ?
C4 C5 C6 C1 2.6(5) . . . . ?
O1 C5 C6 C7 1.6(5) . . . . ?
C4 C5 C6 C7 -178.6(3) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C5 C6 C7 O2 173.5(3) . . . . ?
C1 C6 C7 O2 -7.8(5) . . . . ?
C5 C6 C7 C8 -8.8(4) . . . . ?
C1 C6 C7 C8 169.9(3) . . . . ?
C10 O3 C8 C9 -151.8(3) . . . . ?
C10 O3 C8 C7 89.9(3) . . . . ?
C10 O3 C8 C12 -26.0(3) . . . . ?
O2 C7 C8 O3 -29.9(4) . . . . ?
C6 C7 C8 O3 152.3(3) . . . . ?
O2 C7 C8 C9 -147.0(3) . . . . ?
C6 C7 C8 C9 35.2(4) . . . . ?
O2 C7 C8 C12 83.6(4) . . . . ?
C6 C7 C8 C12 -94.2(3) . . . . ?
C5 O1 C9 C8 51.9(4) . . . . ?
O3 C8 C9 O1 -173.9(2) . . . . ?
C7 C8 C9 O1 -56.6(4) . . . . ?
C12 C8 C9 O1 67.8(4) . . . . ?
C8 O3 C10 O4 -176.1(4) . . . . ?
C8 O3 C10 C11 6.2(4) . . . . ?
C19 N1 C11 C10 143.3(3) . . . . ?
C19 N1 C11 C12 -98.4(4) . . . . ?
O4 C10 C11 N1 -36.1(6) . . . . ?
O3 C10 C11 N1 141.4(3) . . . . ?
O4 C10 C11 C12 -161.5(4) . . . . ?
O3 C10 C11 C12 16.1(4) . . . . ?
O3 C8 C12 C13 -87.4(3) . . . . ?
C9 C8 C12 C13 32.3(4) . . . . ?
C7 C8 C12 C13 157.2(3) . . . . ?
O3 C8 C12 C11 33.4(3) . . . . ?
C9 C8 C12 C11 153.0(3) . . . . ?
C7 C8 C12 C11 -82.0(3) . . . . ?
N1 C11 C12 C13 -28.3(4) . . . . ?
C10 C11 C12 C13 94.2(3) . . . . ?
N1 C11 C12 C8 -151.7(3) . . . . ?
C10 C11 C12 C8 -29.2(3) . . . . ?
C8 C12 C13 C18 -125.4(4) . . . . ?
C11 C12 C13 C18 121.1(4) . . . . ?
C8 C12 C13 C14 60.9(4) . . . . ?
C11 C12 C13 C14 -52.6(4) . . . . ?
C18 C13 C14 C15 0.0(6) . . . . ?
C12 C13 C14 C15 173.7(3) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C15 C16 C17 C18 -1.4(8) . . . . ?
C14 C13 C18 C17 -0.5(7) . . . . ?
C12 C13 C18 C17 -174.4(4) . . . . ?
C16 C17 C18 C13 1.2(8) . . . . ?
C11 N1 C19 O5 -10.6(5) . . . . ?
C11 N1 C19 C20 171.8(3) . . . . ?
O5 C19 C20 C21 -46.9(5) . . . . ?
N1 C19 C20 C21 130.7(3) . . . . ?
O5 C19 C20 C25 132.5(4) . . . . ?
N1 C19 C20 C25 -50.0(4) . . . . ?
C25 C20 C21 C22 2.0(5) . . . . ?
C19 C20 C21 C22 -178.7(3) . . . . ?
C20 C21 C22 C23 -1.4(6) . . . . ?
C21 C22 C23 C24 -0.8(7) . . . . ?
C22 C23 C24 C25 2.2(6) . . . . ?
C23 C24 C25 C20 -1.6(6) . . . . ?
C21 C20 C25 C24 -0.6(5) . . . . ?
C19 C20 C25 C24 -179.9(3) . . . . ?

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_202106179
_database_code_depnum_ccdc_archive 'CCDC 2092642'
loop_
_audit_author_name
_audit_author_address
ywp
;Zhengzhou University
China
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 N O5'
_chemical_formula_weight         427.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.9006(3)
_cell_length_b                   13.6924(3)
_cell_length_c                   14.8031(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2209.44(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.732
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8381
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.399
_diffrn_reflns_theta_max         70.898
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4175
_reflns_number_gt                3651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.0742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4175
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5103(3) 0.1764(2) 0.1831(2) 0.0542(7) Uani 1 1 d . . . . .
C2 C 0.4980(3) 0.18090(19) 0.2852(2) 0.0499(6) Uani 1 1 d . . . . .
H2 H 0.4678 0.1174 0.3060 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6329(2) 0.19114(19) 0.3161(2) 0.0489(6) Uani 1 1 d . . . . .
H3 H 0.6439 0.1613 0.3757 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6962(2) 0.1281(2) 0.2425(2) 0.0510(6) Uani 1 1 d . . . . .
C5 C 0.6876(2) 0.0188(2) 0.2673(2) 0.0508(6) Uani 1 1 d . . . . .
C6 C 0.7963(2) -0.0213(2) 0.3122(2) 0.0513(6) Uani 1 1 d . . . . .
C7 C 0.8990(3) 0.0370(2) 0.3273(3) 0.0584(7) Uani 1 1 d . . . . .
C8 C 0.9975(3) 0.0015(3) 0.3766(3) 0.0731(10) Uani 1 1 d . . . . .
H8 H 1.0652 0.0410 0.3878 0.088 Uiso 1 1 calc R U . . .
C9 C 0.9940(3) -0.0929(3) 0.4089(3) 0.0775(10) Uani 1 1 d . . . . .
H9 H 1.0602 -0.1163 0.4421 0.093 Uiso 1 1 calc R U . . .
C10 C 0.8942(3) -0.1544(2) 0.3931(3) 0.0641(8) Uani 1 1 d . . . . .
C11 C 0.7962(3) -0.1172(2) 0.3454(2) 0.0549(7) Uani 1 1 d . . . . .
H11 H 0.7283 -0.1567 0.3349 0.066 Uiso 1 1 calc R U . . .
C12 C 0.8297(3) 0.1514(2) 0.2206(3) 0.0619(8) Uani 1 1 d . . . . .
H12A H 0.8560 0.1127 0.1692 0.074 Uiso 1 1 calc R U . . .
H12B H 0.8372 0.2198 0.2045 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6716(2) 0.29802(19) 0.3185(2) 0.0525(6) Uani 1 1 d . . . . .
C14 C 0.6818(3) 0.3546(2) 0.2410(3) 0.0674(8) Uani 1 1 d . . . . .
H14 H 0.6686 0.3264 0.1846 0.081 Uiso 1 1 calc R U . . .
C15 C 0.7114(4) 0.4521(3) 0.2470(4) 0.0871(13) Uani 1 1 d . . . . .
H15 H 0.7204 0.4887 0.1945 0.105 Uiso 1 1 calc R U . . .
C16 C 0.7277(3) 0.4959(3) 0.3289(5) 0.0987(18) Uani 1 1 d . . . . .
H16 H 0.7469 0.5619 0.3323 0.118 Uiso 1 1 calc R U . . .
C17 C 0.7155(3) 0.4414(3) 0.4063(4) 0.0899(14) Uani 1 1 d . . . . .
H17 H 0.7258 0.4710 0.4624 0.108 Uiso 1 1 calc R U . . .
C18 C 0.6880(3) 0.3420(2) 0.4017(3) 0.0670(8) Uani 1 1 d . . . . .
H18 H 0.6806 0.3055 0.4544 0.080 Uiso 1 1 calc R U . . .
C19 C 0.8937(4) -0.2577(3) 0.4286(3) 0.0851(12) Uani 1 1 d . . . . .
H19A H 0.8139 -0.2729 0.4522 0.128 Uiso 1 1 calc R U . . .
H19B H 0.9537 -0.2639 0.4756 0.128 Uiso 1 1 calc R U . . .
H19C H 0.9131 -0.3020 0.3804 0.128 Uiso 1 1 calc R U . . .
C20 C 0.3106(3) 0.2305(2) 0.3609(2) 0.0523(6) Uani 1 1 d . . . . .
C21 C 0.2341(3) 0.3136(2) 0.3932(2) 0.0513(6) Uani 1 1 d . . . . .
C22 C 0.1077(3) 0.3044(3) 0.3896(3) 0.0764(10) Uani 1 1 d . . . . .
H22 H 0.0725 0.2491 0.3639 0.092 Uiso 1 1 calc R U . . .
C23 C 0.0341(3) 0.3774(4) 0.4244(4) 0.1021(17) Uani 1 1 d . . . . .
H23 H -0.0508 0.3706 0.4224 0.123 Uiso 1 1 calc R U . . .
C24 C 0.0844(4) 0.4593(3) 0.4615(4) 0.0930(14) Uani 1 1 d . . . . .
H24 H 0.0340 0.5082 0.4845 0.112 Uiso 1 1 calc R U . . .
C25 C 0.2092(4) 0.4695(2) 0.4649(3) 0.0738(10) Uani 1 1 d . . . . .
H25 H 0.2436 0.5253 0.4902 0.089 Uiso 1 1 calc R U . . .
C26 C 0.2844(3) 0.3971(2) 0.4307(2) 0.0572(7) Uani 1 1 d . . . . .
H26 H 0.3692 0.4045 0.4329 0.069 Uiso 1 1 calc R U . . .
N1 N 0.4146(2) 0.25422(17) 0.31677(19) 0.0516(5) Uani 1 1 d . . . . .
H1 H 0.427(3) 0.311(3) 0.303(2) 0.052(9) Uiso 1 1 d . . . . .
O1 O 0.4364(2) 0.1979(2) 0.12706(18) 0.0704(6) Uani 1 1 d . . . . .
O2 O 0.6242(2) 0.14428(16) 0.16150(15) 0.0580(5) Uani 1 1 d . . . . .
O3 O 0.59515(19) -0.02713(15) 0.25152(19) 0.0637(6) Uani 1 1 d . . . . .
O4 O 0.90585(19) 0.13072(16) 0.29621(19) 0.0666(6) Uani 1 1 d . . . . .
O5 O 0.2802(2) 0.14647(16) 0.3744(2) 0.0827(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.193(4) . ?
C1 O2 1.355(4) . ?
C1 C2 1.520(4) . ?
C2 N1 1.432(3) . ?
C2 C3 1.546(4) . ?
C2 H2 0.9800 . ?
C3 C13 1.524(4) . ?
C3 C4 1.552(4) . ?
C3 H3 0.9800 . ?
C4 O2 1.451(4) . ?
C4 C12 1.525(4) . ?
C4 C5 1.543(4) . ?
C5 O3 1.211(4) . ?
C5 C6 1.465(4) . ?
C6 C7 1.393(4) . ?
C6 C11 1.402(4) . ?
C7 O4 1.366(4) . ?
C7 C8 1.386(5) . ?
C8 C9 1.378(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(4) . ?
C10 C19 1.508(5) . ?
C11 H11 0.9300 . ?
C12 O4 1.423(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.382(5) . ?
C13 C14 1.389(5) . ?
C14 C15 1.377(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O5 1.215(4) . ?
C20 N1 1.348(4) . ?
C20 C21 1.490(4) . ?
C21 C26 1.384(4) . ?
C21 C22 1.385(4) . ?
C22 C23 1.381(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 H1 0.81(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 122.4(3) . . ?
O1 C1 C2 128.5(3) . . ?
O2 C1 C2 109.2(3) . . ?
N1 C2 C1 114.1(2) . . ?
N1 C2 C3 116.3(2) . . ?
C1 C2 C3 102.3(2) . . ?
N1 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C13 C3 C2 111.0(2) . . ?
C13 C3 C4 115.3(2) . . ?
C2 C3 C4 99.5(2) . . ?
C13 C3 H3 110.2 . . ?
C2 C3 H3 110.2 . . ?
C4 C3 H3 110.2 . . ?
O2 C4 C12 107.9(3) . . ?
O2 C4 C5 108.2(2) . . ?
C12 C4 C5 108.2(2) . . ?
O2 C4 C3 104.7(2) . . ?
C12 C4 C3 117.2(3) . . ?
C5 C4 C3 110.2(2) . . ?
O3 C5 C6 124.5(3) . . ?
O3 C5 C4 120.6(3) . . ?
C6 C5 C4 114.9(2) . . ?
C7 C6 C11 118.7(3) . . ?
C7 C6 C5 120.6(3) . . ?
C11 C6 C5 120.6(2) . . ?
O4 C7 C8 117.7(3) . . ?
O4 C7 C6 121.9(3) . . ?
C8 C7 C6 120.5(3) . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 122.0(3) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C11 C10 C9 117.8(3) . . ?
C11 C10 C19 121.5(3) . . ?
C9 C10 C19 120.7(3) . . ?
C10 C11 C6 121.7(3) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
O4 C12 C4 110.3(3) . . ?
O4 C12 H12A 109.6 . . ?
C4 C12 H12A 109.6 . . ?
O4 C12 H12B 109.6 . . ?
C4 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C18 C13 C14 118.9(3) . . ?
C18 C13 C3 118.4(3) . . ?
C14 C13 C3 122.6(3) . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 119.8(4) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 N1 122.5(3) . . ?
O5 C20 C21 121.2(3) . . ?
N1 C20 C21 116.3(2) . . ?
C26 C21 C22 119.1(3) . . ?
C26 C21 C20 122.5(3) . . ?
C22 C21 C20 118.3(3) . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.8(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.8(4) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.2(4) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C20 N1 C2 121.5(2) . . ?
C20 N1 H1 119(2) . . ?
C2 N1 H1 119(2) . . ?
C1 O2 C4 110.5(2) . . ?
C7 O4 C12 114.9(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
O1 C1 C2 N1 -28.3(4) . . . . ?
O2 C1 C2 N1 150.6(2) . . . . ?
O1 C1 C2 C3 -154.8(3) . . . . ?
O2 C1 C2 C3 24.1(3) . . . . ?
N1 C2 C3 C13 -37.6(4) . . . . ?
C1 C2 C3 C13 87.6(3) . . . . ?
N1 C2 C3 C4 -159.5(2) . . . . ?
C1 C2 C3 C4 -34.3(3) . . . . ?
C13 C3 C4 O2 -84.3(3) . . . . ?
C2 C3 C4 O2 34.4(3) . . . . ?
C13 C3 C4 C12 35.2(4) . . . . ?
C2 C3 C4 C12 153.9(3) . . . . ?
C13 C3 C4 C5 159.5(2) . . . . ?
C2 C3 C4 C5 -81.8(3) . . . . ?
O2 C4 C5 O3 -32.6(4) . . . . ?
C12 C4 C5 O3 -149.2(3) . . . . ?
C3 C4 C5 O3 81.4(4) . . . . ?
O2 C4 C5 C6 149.0(2) . . . . ?
C12 C4 C5 C6 32.3(4) . . . . ?
C3 C4 C5 C6 -97.1(3) . . . . ?
O3 C5 C6 C7 179.7(3) . . . . ?
C4 C5 C6 C7 -1.9(4) . . . . ?
O3 C5 C6 C11 -4.0(5) . . . . ?
C4 C5 C6 C11 174.3(3) . . . . ?
C11 C6 C7 O4 179.4(3) . . . . ?
C5 C6 C7 O4 -4.3(5) . . . . ?
C11 C6 C7 C8 -2.0(5) . . . . ?
C5 C6 C7 C8 174.4(3) . . . . ?
O4 C7 C8 C9 -179.8(4) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C8 C9 C10 0.2(7) . . . . ?
C8 C9 C10 C11 -1.4(6) . . . . ?
C8 C9 C10 C19 179.4(4) . . . . ?
C9 C10 C11 C6 0.9(5) . . . . ?
C19 C10 C11 C6 -179.9(3) . . . . ?
C7 C6 C11 C10 0.8(5) . . . . ?
C5 C6 C11 C10 -175.6(3) . . . . ?
O2 C4 C12 O4 -176.3(2) . . . . ?
C5 C4 C12 O4 -59.5(3) . . . . ?
C3 C4 C12 O4 65.9(3) . . . . ?
C2 C3 C13 C18 108.1(3) . . . . ?
C4 C3 C13 C18 -139.7(3) . . . . ?
C2 C3 C13 C14 -66.8(4) . . . . ?
C4 C3 C13 C14 45.3(4) . . . . ?
C18 C13 C14 C15 1.9(5) . . . . ?
C3 C13 C14 C15 176.8(3) . . . . ?
C13 C14 C15 C16 -1.9(6) . . . . ?
C14 C15 C16 C17 0.6(6) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C14 C13 C18 C17 -0.7(5) . . . . ?
C3 C13 C18 C17 -175.8(3) . . . . ?
C16 C17 C18 C13 -0.6(5) . . . . ?
O5 C20 C21 C26 139.3(4) . . . . ?
N1 C20 C21 C26 -40.4(4) . . . . ?
O5 C20 C21 C22 -37.4(5) . . . . ?
N1 C20 C21 C22 143.0(3) . . . . ?
C26 C21 C22 C23 -0.9(6) . . . . ?
C20 C21 C22 C23 175.9(4) . . . . ?
C21 C22 C23 C24 0.7(8) . . . . ?
C22 C23 C24 C25 -0.3(8) . . . . ?
C23 C24 C25 C26 0.1(7) . . . . ?
C24 C25 C26 C21 -0.3(6) . . . . ?
C22 C21 C26 C25 0.7(5) . . . . ?
C20 C21 C26 C25 -175.9(3) . . . . ?
O5 C20 N1 C2 -1.9(5) . . . . ?
C21 C20 N1 C2 177.8(3) . . . . ?
C1 C2 N1 C20 115.3(3) . . . . ?
C3 C2 N1 C20 -125.8(3) . . . . ?
O1 C1 O2 C4 177.3(3) . . . . ?
C2 C1 O2 C4 -1.7(3) . . . . ?
C12 C4 O2 C1 -147.1(2) . . . . ?
C5 C4 O2 C1 96.0(3) . . . . ?
C3 C4 O2 C1 -21.5(3) . . . . ?
C8 C7 O4 C12 157.3(3) . . . . ?
C6 C7 O4 C12 -24.0(4) . . . . ?
C4 C12 O4 C7 56.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.81(4) 2.37(4) 3.162(3) 164(3) 4_655

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_20210717b4-1
_database_code_depnum_ccdc_archive 'CCDC 2097681'
loop_
_audit_author_name
_audit_author_address
ywp
;Zhengzhou University
China
;
_audit_update_record             
;
2021-07-20 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_audit_creation_date             2021-07-19
_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 H21 N O4'
_chemical_formula_sum            'C25 H21 N O4'
_chemical_formula_weight         399.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.9905(2)
_cell_length_b                   10.36670(10)
_cell_length_c                   25.5652(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3972.88(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4743
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      69.8400
_cell_measurement_theta_min      3.4780
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.066
_diffrn_reflns_theta_min         3.458
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  27.00   0.50    0.50    --    0.00 -57.00 -90.00  190
  2  ω     63.00  89.00   0.50    0.50    --    0.00  57.00-180.00   52
  3  ω    109.00 154.00   0.50    5.70    --   98.80 -15.00-150.00   90
  4  ω     82.00 185.00   0.50    5.70    --   98.80  61.00 120.00  206
  5  ω    119.00 147.00   0.50    5.70    --   98.80  45.00-180.00   56
  6  ω    154.00 188.00   0.50    5.70    --   98.80  45.00-180.00   68
  7  ω     18.00 128.00   0.50    5.70    --   98.80 -61.00 150.00  220
  8  ω     56.00  83.00   0.50    5.70    --   98.80 -15.00-150.00   54
  9  ω     15.00  41.00   0.50    5.70    --   98.80 -15.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0599365000
_diffrn_orient_matrix_UB_12      -0.0148583000
_diffrn_orient_matrix_UB_13      -0.0485500000
_diffrn_orient_matrix_UB_21      -0.0269393000
_diffrn_orient_matrix_UB_22      0.1429698000
_diffrn_orient_matrix_UB_23      0.0042249000
_diffrn_orient_matrix_UB_31      0.0790533000
_diffrn_orient_matrix_UB_32      0.0376827000
_diffrn_orient_matrix_UB_33      -0.0354221000
_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                3052
_reflns_number_total             3765
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0378
_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)+(0.0466P)²+0.7821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1029
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16508(10) 0.17638(13) 0.41213(6) 0.0347(3) Uani 1 1 d . . . . .
O1 O 0.11095(8) 0.11175(11) 0.43381(5) 0.0473(3) Uani 1 1 d . . . . .
N1 N 0.24523(8) 0.26491(11) 0.48710(4) 0.0301(3) Uani 1 1 d . . . . .
H1 H 0.2601(12) 0.191(2) 0.4965(7) 0.049(5) Uiso 1 1 d . . . . .
C2 C 0.21953(9) 0.28738(12) 0.43380(5) 0.0298(3) Uani 1 1 d . . . . .
H2 H 0.1828 0.3655 0.4326 0.036 Uiso 1 1 calc R . . . .
O2 O 0.18693(8) 0.15643(9) 0.36127(4) 0.0415(3) Uani 1 1 d . . . . .
C3 C 0.29692(10) 0.30284(12) 0.39395(5) 0.0305(3) Uani 1 1 d . . . . .
H3 H 0.3102 0.3945 0.3889 0.037 Uiso 1 1 calc R . . . .
O3 O 0.12914(7) 0.36355(11) 0.31046(5) 0.0456(3) Uani 1 1 d . . . . .
C4 C 0.25342(10) 0.24704(13) 0.34390(5) 0.0347(3) Uani 1 1 d . . . . .
H4 H 0.2988 0.2012 0.3235 0.042 Uiso 1 1 calc R . . . .
O4 O 0.25287(8) 0.47738(9) 0.50437(4) 0.0401(3) Uani 1 1 d . . . . .
C5 C 0.20963(10) 0.34891(13) 0.30940(5) 0.0342(3) Uani 1 1 d . . . . .
C6 C 0.26880(10) 0.43099(14) 0.27683(5) 0.0335(3) Uani 1 1 d . . . . .
C7 C 0.36155(10) 0.42464(15) 0.27937(6) 0.0395(3) Uani 1 1 d . . . . .
H7 H 0.3887 0.3616 0.2998 0.047 Uiso 1 1 calc R . . . .
C8 C 0.41351(11) 0.51130(17) 0.25185(6) 0.0454(4) Uani 1 1 d . . . . .
H8 H 0.4753 0.5058 0.2541 0.054 Uiso 1 1 calc R . . . .
C9 C 0.37524(12) 0.60640(16) 0.22099(6) 0.0455(4) Uani 1 1 d . . . . .
C10 C 0.28293(12) 0.60858(16) 0.21671(6) 0.0454(4) Uani 1 1 d . . . . .
H10 H 0.2560 0.6693 0.1951 0.055 Uiso 1 1 calc R . . . .
C11 C 0.23043(11) 0.52257(14) 0.24393(6) 0.0390(3) Uani 1 1 d . . . . .
H11 H 0.1687 0.5257 0.2403 0.047 Uiso 1 1 calc R . . . .
C12 C 0.43122(15) 0.7062(2) 0.19386(8) 0.0656(6) Uani 1 1 d . . . . .
H12A H 0.4336 0.7829 0.2149 0.098 Uiso 1 1 calc GR . . . .
H12B H 0.4053 0.7262 0.1605 0.098 Uiso 1 1 calc GR . . . .
H12C H 0.4905 0.6733 0.1889 0.098 Uiso 1 1 calc GR . . . .
C13 C 0.38054(9) 0.23201(13) 0.41059(5) 0.0313(3) Uani 1 1 d . . . . .
C14 C 0.39295(10) 0.10110(14) 0.40024(6) 0.0380(3) Uani 1 1 d . . . . .
H14 H 0.3504 0.0563 0.3810 0.046 Uiso 1 1 calc R . . . .
C15 C 0.46791(11) 0.03740(15) 0.41829(7) 0.0471(4) Uani 1 1 d . . . . .
H15 H 0.4756 -0.0498 0.4109 0.057 Uiso 1 1 calc R . . . .
C16 C 0.53124(11) 0.10204(17) 0.44708(7) 0.0509(4) Uani 1 1 d . . . . .
H16 H 0.5814 0.0588 0.4593 0.061 Uiso 1 1 calc R . . . .
C17 C 0.51973(11) 0.23207(17) 0.45776(7) 0.0478(4) Uani 1 1 d . . . . .
H17 H 0.5623 0.2762 0.4773 0.057 Uiso 1 1 calc R . . . .
C18 C 0.44515(10) 0.29634(15) 0.43947(6) 0.0393(3) Uani 1 1 d . . . . .
H18 H 0.4382 0.3837 0.4466 0.047 Uiso 1 1 calc R . . . .
C19 C 0.26876(9) 0.36570(12) 0.51778(5) 0.0297(3) Uani 1 1 d . . . . .
C20 C 0.31757(9) 0.33477(13) 0.56701(5) 0.0325(3) Uani 1 1 d . . . . .
C21 C 0.37354(11) 0.42880(16) 0.58740(6) 0.0424(4) Uani 1 1 d . . . . .
H21 H 0.3753 0.5103 0.5722 0.051 Uiso 1 1 calc R . . . .
C22 C 0.42688(12) 0.4018(2) 0.63032(7) 0.0526(4) Uani 1 1 d . . . . .
H22 H 0.4648 0.4648 0.6435 0.063 Uiso 1 1 calc R . . . .
C23 C 0.42386(12) 0.2822(2) 0.65344(7) 0.0541(5) Uani 1 1 d . . . . .
H23 H 0.4603 0.2639 0.6819 0.065 Uiso 1 1 calc R . . . .
C24 C 0.36664(14) 0.18937(18) 0.63429(7) 0.0531(5) Uani 1 1 d . . . . .
H24 H 0.3635 0.1093 0.6506 0.064 Uiso 1 1 calc R . . . .
C25 C 0.31388(12) 0.21434(15) 0.59103(6) 0.0424(4) Uani 1 1 d . . . . .
H25 H 0.2761 0.1508 0.5780 0.051 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
C1 O1 1.1894(18) . ?
C1 C2 1.5157(19) . ?
C1 O2 1.3566(19) . ?
N1 H1 0.84(2) . ?
N1 C2 1.4350(17) . ?
N1 C19 1.3533(17) . ?
C2 H2 0.9800 . ?
C2 C3 1.552(2) . ?
O2 C4 1.4398(18) . ?
C3 H3 0.9800 . ?
C3 C4 1.5483(19) . ?
C3 C13 1.5137(19) . ?
O3 C5 1.2164(18) . ?
C4 H4 0.9800 . ?
C4 C5 1.525(2) . ?
O4 C19 1.2307(16) . ?
C5 C6 1.485(2) . ?
C6 C7 1.393(2) . ?
C6 C11 1.393(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(2) . ?
C9 C10 1.388(3) . ?
C9 C12 1.502(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(2) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.395(2) . ?
C13 C18 1.389(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.491(2) . ?
C20 C21 1.388(2) . ?
C20 C25 1.392(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(2) . ?
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
O1 C1 C2 128.66(14) . . ?
O1 C1 O2 121.70(13) . . ?
O2 C1 C2 109.64(12) . . ?
C2 N1 H1 119.6(13) . . ?
C19 N1 H1 118.3(13) . . ?
C19 N1 C2 119.67(11) . . ?
C1 C2 H2 108.3 . . ?
C1 C2 C3 103.95(11) . . ?
N1 C2 C1 111.62(11) . . ?
N1 C2 H2 108.3 . . ?
N1 C2 C3 116.06(11) . . ?
C3 C2 H2 108.3 . . ?
C1 O2 C4 111.30(10) . . ?
C2 C3 H3 109.8 . . ?
C4 C3 C2 100.90(11) . . ?
C4 C3 H3 109.8 . . ?
C13 C3 C2 112.61(11) . . ?
C13 C3 H3 109.8 . . ?
C13 C3 C4 113.56(11) . . ?
O2 C4 C3 106.28(11) . . ?
O2 C4 H4 109.1 . . ?
O2 C4 C5 109.41(12) . . ?
C3 C4 H4 109.1 . . ?
C5 C4 C3 113.62(11) . . ?
C5 C4 H4 109.1 . . ?
O3 C5 C4 120.04(13) . . ?
O3 C5 C6 122.25(13) . . ?
C6 C5 C4 117.66(12) . . ?
C7 C6 C5 122.88(13) . . ?
C11 C6 C5 118.86(13) . . ?
C11 C6 C7 118.20(14) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.53(15) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.25(15) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 117.95(15) . . ?
C8 C9 C12 121.42(17) . . ?
C10 C9 C12 120.62(17) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.26(15) . . ?
C11 C10 H10 119.4 . . ?
C6 C11 H11 119.7 . . ?
C10 C11 C6 120.68(15) . . ?
C10 C11 H11 119.7 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 121.94(13) . . ?
C18 C13 C3 119.61(12) . . ?
C18 C13 C14 118.36(13) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.65(15) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.45(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.55(15) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.17(16) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.82(14) . . ?
C17 C18 H18 119.6 . . ?
N1 C19 C20 116.83(12) . . ?
O4 C19 N1 120.95(12) . . ?
O4 C19 C20 122.18(12) . . ?
C21 C20 C19 117.56(13) . . ?
C21 C20 C25 119.23(14) . . ?
C25 C20 C19 123.07(13) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.27(16) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.25(17) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.82(16) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.58(17) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.82(16) . . ?
C24 C25 H25 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.84(2) 2.23(2) 3.0135(14) 156.3(17) 8_655

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 25.79(12) . . . . ?
C1 C2 C3 C13 -95.62(13) . . . . ?
C1 O2 C4 C3 18.28(15) . . . . ?
C1 O2 C4 C5 -104.78(13) . . . . ?
O1 C1 C2 N1 36.8(2) . . . . ?
O1 C1 C2 C3 162.66(15) . . . . ?
O1 C1 O2 C4 179.69(14) . . . . ?
N1 C2 C3 C4 148.74(11) . . . . ?
N1 C2 C3 C13 27.33(15) . . . . ?
N1 C19 C20 C21 153.63(13) . . . . ?
N1 C19 C20 C25 -22.0(2) . . . . ?
C2 C1 O2 C4 -0.72(15) . . . . ?
C2 N1 C19 O4 13.7(2) . . . . ?
C2 N1 C19 C20 -163.89(12) . . . . ?
C2 C3 C4 O2 -26.95(13) . . . . ?
C2 C3 C4 C5 93.42(13) . . . . ?
C2 C3 C13 C14 84.16(16) . . . . ?
C2 C3 C13 C18 -92.29(15) . . . . ?
O2 C1 C2 N1 -142.72(12) . . . . ?
O2 C1 C2 C3 -16.89(14) . . . . ?
O2 C4 C5 O3 17.53(18) . . . . ?
O2 C4 C5 C6 -164.82(11) . . . . ?
C3 C4 C5 O3 -101.06(16) . . . . ?
C3 C4 C5 C6 76.59(16) . . . . ?
C3 C13 C14 C15 -176.60(14) . . . . ?
C3 C13 C18 C17 176.23(14) . . . . ?
O3 C5 C6 C7 172.97(14) . . . . ?
O3 C5 C6 C11 -4.0(2) . . . . ?
C4 C3 C13 C14 -29.73(19) . . . . ?
C4 C3 C13 C18 153.81(13) . . . . ?
C4 C5 C6 C7 -4.62(19) . . . . ?
C4 C5 C6 C11 178.37(12) . . . . ?
O4 C19 C20 C21 -24.0(2) . . . . ?
O4 C19 C20 C25 160.37(15) . . . . ?
C5 C6 C7 C8 -173.95(14) . . . . ?
C5 C6 C11 C10 174.00(13) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C7 C6 C11 C10 -3.2(2) . . . . ?
C7 C8 C9 C10 -2.7(2) . . . . ?
C7 C8 C9 C12 175.88(15) . . . . ?
C8 C9 C10 C11 2.7(2) . . . . ?
C9 C10 C11 C6 0.3(2) . . . . ?
C11 C6 C7 C8 3.1(2) . . . . ?
C12 C9 C10 C11 -175.95(15) . . . . ?
C13 C3 C4 O2 93.78(14) . . . . ?
C13 C3 C4 C5 -145.85(12) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C13 C18 C17 -0.3(2) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C13 0.5(3) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C19 N1 C2 C1 -159.38(12) . . . . ?
C19 N1 C2 C3 81.78(15) . . . . ?
C19 C20 C21 C22 -174.10(14) . . . . ?
C19 C20 C25 C24 174.74(15) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C21 C20 C25 C24 -0.9(2) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 1.8(3) . . . . ?
C23 C24 C25 C20 -0.9(3) . . . . ?
C25 C20 C21 C22 1.7(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.477
_oxdiff_exptl_absorpt_empirical_full_min 0.788
