# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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. 
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#######################################################################

data_3-DPyFO-P21c
_database_code_depnum_ccdc_archive 'CCDC 2106424'
loop_
_audit_author_name
_audit_author_address
'Yongshen Zheng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H14 N2 O'
_chemical_formula_sum            'C23 H14 N2 O'
_chemical_formula_weight         334.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.5282(2)
_cell_length_b                   27.6641(6)
_cell_length_c                   8.6003(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.783(3)
_cell_angle_gamma                90
_cell_volume                     1639.00(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2708
_cell_measurement_temperature    300.78(10)
_cell_measurement_theta_max      71.5790
_cell_measurement_theta_min      6.3780
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8101
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.700
_diffrn_reflns_theta_min         3.195
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00   0.00   0.50    2.40    --    0.00  77.00   0.00   74
  2  ω     28.00  89.00   0.50    2.40    --    0.00  57.00  30.00  122
  3  ω    -33.00  11.00   0.50    2.40    --    0.00  57.00  30.00   88
  4  ω     17.00  43.00   0.50    2.40    --    0.00  77.00   0.00   52
  5  ω    117.00 142.00   0.50    9.61    --   98.20  61.00-120.00   50
  6  ω     79.00 151.00   0.50    9.61    --   98.20 -15.00  60.00  144
  7  ω      9.00  74.00   0.50    9.61    --   98.20 -15.00  60.00  130
  8  ω     26.00 112.00   0.50    9.61    --   98.20 -61.00  60.00  172
  9  ω    163.00 188.00   0.50    9.61    --   98.20 -15.00  60.00   50
 10  ω     63.00  89.00   0.50    9.61    --   98.20  61.00-120.00   52
 11  ω     10.00 139.00   0.50    9.61    --   98.20 -77.00  60.00  258
 12  ω     40.00 186.00   0.50    9.61    --   98.20 -15.00 150.00  292
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1746224000
_diffrn_orient_matrix_UB_12      -0.0285705000
_diffrn_orient_matrix_UB_13      -0.1252940000
_diffrn_orient_matrix_UB_21      -0.0650956000
_diffrn_orient_matrix_UB_22      0.0447291000
_diffrn_orient_matrix_UB_23      -0.1160262000
_diffrn_orient_matrix_UB_31      0.1234849000
_diffrn_orient_matrix_UB_32      -0.0168641000
_diffrn_orient_matrix_UB_33      -0.0956789000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2401
_reflns_number_total             3231
_reflns_odcompleteness_completeness 99.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.1524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C24, C23
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C24 \\sim N3 \\sim C21: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C23 \\sim C24: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C24 \\sim C23: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C24) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
4.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C10(H10), C7(H7), C8(H8), C15(H15), C16(H16), C22(H22), C5(H5),
 C21(H21), C24(H24), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6782(2) 0.44860(4) 0.45458(15) 0.0717(4) Uani 1 1 d . . . . .
C9 C 0.7988(2) 0.54266(6) 0.23804(19) 0.0497(4) Uani 1 1 d . . . . .
C13 C 0.7180(2) 0.46081(6) 0.19094(19) 0.0498(4) Uani 1 1 d . . . . .
C14 C 0.7638(2) 0.50181(6) 0.11923(19) 0.0492(4) Uani 1 1 d . . . . .
C11 C 0.7710(2) 0.52669(6) 0.38126(19) 0.0493(4) Uani 1 1 d . . . . .
C17 C 0.6810(2) 0.41264(6) -0.05260(19) 0.0507(4) Uani 1 1 d . . . . .
C12 C 0.7181(2) 0.47448(6) 0.35848(19) 0.0541(4) Uani 1 1 d . . . . .
C6 C 0.8368(2) 0.60603(6) 0.5040(2) 0.0524(4) Uani 1 1 d . . . . .
C18 C 0.6779(2) 0.41706(6) 0.10886(19) 0.0533(4) Uani 1 1 d . . . . .
H18 H 0.6481 0.3898 0.1612 0.064 Uiso 1 1 calc R . . . .
C20 C 0.6406(2) 0.36568(6) -0.14263(19) 0.0538(4) Uani 1 1 d . . . . .
C10 C 0.7879(2) 0.55739(6) 0.5118(2) 0.0538(4) Uani 1 1 d . . . . .
H10 H 0.7667 0.5458 0.6069 0.065 Uiso 1 1 calc R . . . .
C4 C 0.8495(2) 0.64025(6) 0.6399(2) 0.0556(4) Uani 1 1 d . . . . .
C7 C 0.8678(2) 0.62118(6) 0.3622(2) 0.0580(4) Uani 1 1 d . . . . .
H7 H 0.9032 0.6539 0.3563 0.070 Uiso 1 1 calc R . . . .
C8 C 0.8489(2) 0.59021(6) 0.2291(2) 0.0575(4) Uani 1 1 d . . . . .
H8 H 0.8701 0.6016 0.1338 0.069 Uiso 1 1 calc R . . . .
C15 C 0.7648(2) 0.49839(6) -0.0412(2) 0.0561(4) Uani 1 1 d . . . . .
H15 H 0.7936 0.5259 -0.0932 0.067 Uiso 1 1 calc R . . . .
N2 N 0.7288(3) 0.66443(6) 0.8494(2) 0.0819(5) Uani 1 1 d . . . . .
C16 C 0.7230(2) 0.45426(6) -0.1247(2) 0.0568(4) Uani 1 1 d . . . . .
H16 H 0.7227 0.4521 -0.2350 0.068 Uiso 1 1 calc R . . . .
C19 C 0.5417(3) 0.32892(7) -0.1007(2) 0.0661(5) Uani 1 1 d . . . . .
H19 H 0.494(3) 0.3349(7) -0.012(3) 0.079 Uiso 1 1 d R . . . .
C22 C 0.9810(3) 0.67835(7) 0.6912(3) 0.0681(5) Uani 1 1 d . . . . .
H22 H 1.0676 0.6836 0.6374 0.082 Uiso 1 1 calc R . . . .
C5 C 0.7253(3) 0.63594(7) 0.7233(2) 0.0678(5) Uani 1 1 d . . . . .
H5 H 0.6313 0.6108 0.6875 0.081 Uiso 1 1 calc R . . . .
N3 N 0.6723(3) 0.31221(8) -0.3513(3) 0.1014(6) Uani 1 1 d . U . . .
C21 C 0.6993(3) 0.35551(8) -0.2728(2) 0.0741(5) Uani 1 1 d . U . . .
H21 H 0.7618 0.3803 -0.3085 0.089 Uiso 1 1 calc R . . . .
C24 C 0.5115(3) 0.28553(7) -0.1782(3) 0.0731(5) Uani 1 1 d . U . . .
H24 H 0.4444 0.2607 -0.1477 0.088 Uiso 1 1 calc R . . . .
C1 C 0.8598(4) 0.69997(8) 0.8968(3) 0.0813(6) Uani 1 1 d . . . . .
H1 H 0.8664 0.7204 0.9878 0.098 Uiso 1 1 calc R . . . .
C2 C 0.9853(3) 0.70846(7) 0.8205(3) 0.0785(6) Uani 1 1 d . . . . .
H2 H 1.0741 0.7347 0.8562 0.094 Uiso 1 1 calc R . . . .
C23 C 0.5784(4) 0.27806(9) -0.3000(3) 0.0896(7) Uani 1 1 d . U . . .
H23 H 0.560(4) 0.2462(9) -0.345(3) 0.107 Uiso 1 1 d 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 C12 1.2191(18) . ?
C9 C14 1.474(2) . ?
C9 C11 1.402(2) . ?
C9 C8 1.379(2) . ?
C13 C14 1.399(2) . ?
C13 C12 1.489(2) . ?
C13 C18 1.372(2) . ?
C14 C15 1.386(2) . ?
C11 C12 1.490(2) . ?
C11 C10 1.372(2) . ?
C17 C18 1.404(2) . ?
C17 C20 1.480(2) . ?
C17 C16 1.403(2) . ?
C6 C10 1.404(2) . ?
C6 C4 1.477(2) . ?
C6 C7 1.395(2) . ?
C18 H18 0.9500 . ?
C20 C19 1.391(2) . ?
C20 C21 1.389(2) . ?
C10 H10 0.9500 . ?
C4 C22 1.390(2) . ?
C4 C5 1.394(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(2) . ?
C8 H8 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
N2 C5 1.333(2) . ?
N2 C1 1.335(3) . ?
C16 H16 0.9500 . ?
C19 H19 0.98(2) . ?
C19 C24 1.347(3) . ?
C22 H22 0.9500 . ?
C22 C2 1.379(3) . ?
C5 H5 0.9500 . ?
N3 C21 1.349(3) . ?
N3 C23 1.356(3) . ?
C21 H21 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.348(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.370(3) . ?
C2 H2 0.9500 . ?
C23 H23 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C9 C14 108.62(13) . . ?
C8 C9 C14 132.00(14) . . ?
C8 C9 C11 119.38(15) . . ?
C14 C13 C12 108.46(14) . . ?
C18 C13 C14 122.05(14) . . ?
C18 C13 C12 129.48(14) . . ?
C13 C14 C9 108.83(13) . . ?
C15 C14 C9 132.17(15) . . ?
C15 C14 C13 118.98(15) . . ?
C9 C11 C12 108.47(13) . . ?
C10 C11 C9 121.77(15) . . ?
C10 C11 C12 129.74(14) . . ?
C18 C17 C20 120.79(14) . . ?
C16 C17 C18 117.54(15) . . ?
C16 C17 C20 121.67(14) . . ?
O1 C12 C13 127.06(16) . . ?
O1 C12 C11 127.30(15) . . ?
C13 C12 C11 105.61(12) . . ?
C10 C6 C4 120.74(14) . . ?
C7 C6 C10 117.99(15) . . ?
C7 C6 C4 121.25(15) . . ?
C13 C18 C17 119.85(15) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C20 C17 121.68(14) . . ?
C21 C20 C17 122.30(15) . . ?
C21 C20 C19 116.02(17) . . ?
C11 C10 C6 119.59(15) . . ?
C11 C10 H10 120.2 . . ?
C6 C10 H10 120.2 . . ?
C22 C4 C6 123.22(15) . . ?
C22 C4 C5 116.16(17) . . ?
C5 C4 C6 120.62(15) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.46(15) . . ?
C8 C7 H7 118.8 . . ?
C9 C8 C7 118.79(14) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.98(15) . . ?
C16 C15 H15 120.5 . . ?
C5 N2 C1 116.95(18) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 C17 122.58(14) . . ?
C15 C16 H16 118.7 . . ?
C20 C19 H19 118.9(11) . . ?
C24 C19 C20 121.63(17) . . ?
C24 C19 H19 119.5(11) . . ?
C4 C22 H22 120.1 . . ?
C2 C22 C4 119.74(18) . . ?
C2 C22 H22 120.1 . . ?
C4 C5 H5 117.6 . . ?
N2 C5 C4 124.83(18) . . ?
N2 C5 H5 117.6 . . ?
C21 N3 C23 116.68(19) . . ?
C20 C21 H21 118.3 . . ?
N3 C21 C20 123.38(19) . . ?
N3 C21 H21 118.3 . . ?
C19 C24 H24 120.7 . . ?
C19 C24 C23 118.66(19) . . ?
C23 C24 H24 120.7 . . ?
N2 C1 H1 118.4 . . ?
N2 C1 C2 123.2(2) . . ?
C2 C1 H1 118.4 . . ?
C22 C2 H2 120.5 . . ?
C1 C2 C22 119.07(19) . . ?
C1 C2 H2 120.5 . . ?
N3 C23 H23 121.4(15) . . ?
C24 C23 N3 123.6(2) . . ?
C24 C23 H23 115.0(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
C9 C14 C15 C16 -179.10(15) . . . . ?
C9 C11 C12 O1 -177.95(17) . . . . ?
C9 C11 C12 C13 0.31(16) . . . . ?
C9 C11 C10 C6 -0.8(2) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C9 C11 C12 0.39(16) . . . . ?
C14 C9 C11 C10 -178.00(14) . . . . ?
C14 C9 C8 C7 178.49(16) . . . . ?
C14 C13 C12 O1 177.33(17) . . . . ?
C14 C13 C12 C11 -0.93(16) . . . . ?
C14 C13 C18 C17 -0.4(2) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C11 C9 C14 C13 -1.01(17) . . . . ?
C11 C9 C14 C15 177.33(16) . . . . ?
C11 C9 C8 C7 -0.8(2) . . . . ?
C17 C20 C19 C24 -177.38(17) . . . . ?
C17 C20 C21 N3 176.73(19) . . . . ?
C12 C13 C14 C9 1.19(16) . . . . ?
C12 C13 C14 C15 -177.40(13) . . . . ?
C12 C13 C18 C17 178.10(15) . . . . ?
C12 C11 C10 C6 -178.84(15) . . . . ?
C6 C4 C22 C2 -179.28(16) . . . . ?
C6 C4 C5 N2 178.53(17) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C18 C13 C14 C9 179.97(14) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
C18 C13 C12 O1 -1.3(3) . . . . ?
C18 C13 C12 C11 -179.59(15) . . . . ?
C18 C17 C20 C19 20.3(2) . . . . ?
C18 C17 C20 C21 -159.42(17) . . . . ?
C18 C17 C16 C15 1.5(2) . . . . ?
C20 C17 C18 C13 179.27(14) . . . . ?
C20 C17 C16 C15 -178.79(15) . . . . ?
C20 C19 C24 C23 -0.4(3) . . . . ?
C10 C11 C12 O1 0.3(3) . . . . ?
C10 C11 C12 C13 178.53(16) . . . . ?
C10 C6 C4 C22 146.31(17) . . . . ?
C10 C6 C4 C5 -34.4(2) . . . . ?
C10 C6 C7 C8 1.1(2) . . . . ?
C4 C6 C10 C11 177.91(14) . . . . ?
C4 C6 C7 C8 -177.27(15) . . . . ?
C4 C22 C2 C1 0.4(3) . . . . ?
C7 C6 C10 C11 -0.4(2) . . . . ?
C7 C6 C4 C22 -35.4(2) . . . . ?
C7 C6 C4 C5 143.89(17) . . . . ?
C8 C9 C14 C13 179.60(16) . . . . ?
C8 C9 C14 C15 -2.1(3) . . . . ?
C8 C9 C11 C12 179.88(14) . . . . ?
C8 C9 C11 C10 1.5(2) . . . . ?
N2 C1 C2 C22 -1.7(3) . . . . ?
C16 C17 C18 C13 -1.0(2) . . . . ?
C16 C17 C20 C19 -159.47(16) . . . . ?
C16 C17 C20 C21 20.9(2) . . . . ?
C19 C20 C21 N3 -3.0(3) . . . . ?
C19 C24 C23 N3 -1.1(4) . . . . ?
C22 C4 C5 N2 -2.1(3) . . . . ?
C5 C4 C22 C2 1.4(3) . . . . ?
C5 N2 C1 C2 1.1(3) . . . . ?
C21 C20 C19 C24 2.3(3) . . . . ?
C21 N3 C23 C24 0.6(4) . . . . ?
C1 N2 C5 C4 0.9(3) . . . . ?
C23 N3 C21 C20 1.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.764
####################################################################### 
# 
# 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_3-DPyFO-Pccn
_database_code_depnum_ccdc_archive 'CCDC 2106426'
loop_
_audit_author_name
_audit_author_address
'Yongshen Zheng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-09-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 N2 O'
_chemical_formula_sum            'C23 H14 N2 O'
_chemical_formula_weight         334.36
_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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   30.1793(7)
_cell_length_b                   13.6976(3)
_cell_length_c                   7.76620(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3210.42(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3812
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9320
_cell_measurement_theta_min      6.7010
_shelx_estimated_absorpt_T_max   0.822
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.920
_diffrn_reflns_theta_min         3.544
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  34.00   0.50    3.35    --    0.00  82.00  30.00   56
  2  ω    -33.00   3.00   0.50    3.35    --    0.00  82.00  30.00   72
  3  ω    -26.00  39.00   0.50    3.35    --    0.00  82.00 -90.00  130
  4  ω     19.00  50.00   0.50   30.00    --  102.30 -82.00-180.00   62
  5  ω     79.00 112.00   0.50   30.00    --  102.30 -82.00-180.00   66
  6  ω     24.00 120.00   0.50   30.00    --  102.30 -19.00  30.00  192
  7  ω     39.00 132.00   0.50   30.00    --  102.30 -77.00 -30.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0500581000
_diffrn_orient_matrix_UB_12      0.0214396000
_diffrn_orient_matrix_UB_13      -0.0028401000
_diffrn_orient_matrix_UB_21      -0.0099242000
_diffrn_orient_matrix_UB_22      0.1093573000
_diffrn_orient_matrix_UB_23      -0.0259021000
_diffrn_orient_matrix_UB_31      -0.0005073000
_diffrn_orient_matrix_UB_32      0.0148419000
_diffrn_orient_matrix_UB_33      0.1967769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2636
_reflns_number_total             3230
_reflns_odcompleteness_completeness 98.91
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     308
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.034
_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)+(0.1189P)²+0.5465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1795
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C27-C17 = C19-C17
 1.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 1.7A
4. Others
 Sof(C19)=Sof(C20)=Sof(H20)=Sof(C18)=Sof(H18)=Sof(N3)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24)=1-FVAR(1)
 Sof(N2)=Sof(C29)=Sof(H29)=Sof(C26)=Sof(H26)=Sof(C28)=Sof(H28)=Sof(C27)=
 Sof(C30)=Sof(H30)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C22(H22), C8(H8), C7(H7), C5(H5), C15(H15), C16(H16), C3(H3),
 C1(H1), C2(H2), C20(H20), C18(H18), C23(H23), C24(H24), C29(H29), C26(H26),
 C28(H28), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.46142(4) 0.56664(10) 0.14246(16) 0.0398(3) Uani 1 1 d . U . . .
N1 N 0.28918(6) 0.57420(13) 0.6979(2) 0.0493(4) Uani 1 1 d . U . . .
C10 C 0.46419(6) 0.61176(12) 0.4445(2) 0.0353(4) Uani 1 1 d . U . . .
C12 C 0.48232(6) 0.59107(12) 0.2699(2) 0.0350(4) Uani 1 1 d . U . . .
C11 C 0.42081(6) 0.60945(12) 0.4984(2) 0.0355(4) Uani 1 1 d . U . . .
H11 H 0.397855 0.592151 0.420460 0.043 Uiso 1 1 calc R U . . .
C9 C 0.49940(7) 0.63708(12) 0.5535(2) 0.0385(4) Uani 1 1 d . U . . .
C13 C 0.53096(6) 0.60676(12) 0.2833(2) 0.0372(4) Uani 1 1 d . U . . .
C6 C 0.41080(7) 0.63309(12) 0.6709(2) 0.0381(4) Uani 1 1 d . U . . .
C14 C 0.54106(7) 0.63407(12) 0.4540(3) 0.0406(5) Uani 1 1 d . U . . .
C4 C 0.36453(7) 0.63218(13) 0.7339(2) 0.0400(4) Uani 1 1 d . U . . .
C22 C 0.56276(6) 0.59827(13) 0.1582(3) 0.0407(4) Uani 1 1 d . U . . .
H22 H 0.554750 0.579615 0.044565 0.049 Uiso 1 1 calc R U . . .
C8 C 0.49011(7) 0.65939(13) 0.7244(2) 0.0429(5) Uani 1 1 d . U . . .
H8 H 0.513273 0.675924 0.801965 0.051 Uiso 1 1 calc R U . . .
C7 C 0.44641(7) 0.65708(13) 0.7797(2) 0.0429(5) Uani 1 1 d . U . . .
H7 H 0.440254 0.672432 0.896614 0.052 Uiso 1 1 calc R U . . .
C5 C 0.33154(7) 0.58008(14) 0.6484(2) 0.0425(5) Uani 1 1 d . U . . .
H5 H 0.339786 0.546043 0.546722 0.051 Uiso 1 1 calc R U . . .
C17 C 0.60740(6) 0.61737(13) 0.1991(3) 0.0458(5) Uani 1 1 d D U . . .
C15 C 0.58479(7) 0.65253(14) 0.4963(3) 0.0488(5) Uani 1 1 d . U . . .
H15 H 0.592596 0.670804 0.610315 0.059 Uiso 1 1 calc R U . . .
C16 C 0.61732(7) 0.64398(14) 0.3693(3) 0.0517(6) Uani 1 1 d . U . . .
H16 H 0.647299 0.656655 0.399205 0.062 Uiso 1 1 calc R U . . .
C3 C 0.35104(8) 0.68129(16) 0.8821(3) 0.0520(5) Uani 1 1 d . U . . .
H3 H 0.371868 0.718698 0.945751 0.062 Uiso 1 1 calc R U . . .
C1 C 0.27802(8) 0.62181(16) 0.8419(3) 0.0523(5) Uani 1 1 d . U . . .
H1 H 0.248212 0.618148 0.880639 0.063 Uiso 1 1 calc R U . . .
C2 C 0.30784(9) 0.67596(16) 0.9365(3) 0.0576(6) Uani 1 1 d . U . . .
H2 H 0.298640 0.709065 1.037910 0.069 Uiso 1 1 calc R U . . .
C19 C 0.6410(3) 0.6036(8) 0.0522(10) 0.0401(15) Uani 0.600(7) 1 d D U P A 2
C20 C 0.6349(2) 0.5423(6) -0.0912(8) 0.0394(12) Uani 0.600(7) 1 d . U P A 2
H20 H 0.607996 0.506606 -0.096425 0.047 Uiso 0.600(7) 1 calc R U P A 2
C18 C 0.68293(19) 0.6530(4) 0.0516(7) 0.0444(11) Uani 0.600(7) 1 d . U P A 2
H18 H 0.689971 0.695893 0.143794 0.053 Uiso 0.600(7) 1 calc R U P A 2
N3 N 0.66410(11) 0.5292(2) -0.2236(5) 0.0432(9) Uani 0.600(7) 1 d . U P A 2
C23 C 0.70247(13) 0.5778(3) -0.2157(6) 0.0441(10) Uani 0.600(7) 1 d . U P A 2
H23 H 0.723181 0.569777 -0.306663 0.053 Uiso 0.600(7) 1 calc R U P A 2
C24 C 0.7134(2) 0.6398(5) -0.0799(9) 0.0483(14) Uani 0.600(7) 1 d . U P A 2
H24 H 0.741244 0.672360 -0.077409 0.058 Uiso 0.600(7) 1 calc R U P A 2
N2 N 0.71314(17) 0.6762(4) 0.0009(9) 0.0487(14) Uani 0.400(7) 1 d . U P A 1
C29 C 0.6766(2) 0.5504(5) -0.1541(10) 0.0493(13) Uani 0.400(7) 1 d . U P A 1
H29 H 0.676605 0.506306 -0.248557 0.059 Uiso 0.400(7) 1 calc R U P A 1
C26 C 0.6789(3) 0.6780(6) 0.1102(11) 0.0468(16) Uani 0.400(7) 1 d . U P A 1
H26 H 0.678795 0.723009 0.203217 0.056 Uiso 0.400(7) 1 calc R U P A 1
C28 C 0.6416(4) 0.5522(10) -0.0428(14) 0.0441(19) Uani 0.400(7) 1 d . U P A 1
H28 H 0.616617 0.510877 -0.057134 0.053 Uiso 0.400(7) 1 calc R U P A 1
C27 C 0.6446(5) 0.6164(13) 0.0891(17) 0.043(2) Uani 0.400(7) 1 d D U P A 1
C30 C 0.7111(4) 0.6113(7) -0.1297(14) 0.048(2) Uani 0.400(7) 1 d . U P A 1
H30 H 0.735194 0.608350 -0.208268 0.058 Uiso 0.400(7) 1 calc R U P A 1


_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 C12 1.221(2) . ?
N1 C5 1.337(3) . ?
N1 C1 1.337(3) . ?
C10 C12 1.489(3) . ?
C10 C11 1.375(3) . ?
C10 C9 1.402(2) . ?
C12 C13 1.487(3) . ?
C11 H11 0.9500 . ?
C11 C6 1.411(2) . ?
C9 C14 1.476(3) . ?
C9 C8 1.391(3) . ?
C13 C14 1.410(3) . ?
C13 C22 1.371(3) . ?
C6 C4 1.480(3) . ?
C6 C7 1.406(3) . ?
C14 C15 1.383(3) . ?
C4 C5 1.394(3) . ?
C4 C3 1.393(3) . ?
C22 H22 0.9500 . ?
C22 C17 1.409(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(3) . ?
C7 H7 0.9500 . ?
C5 H5 0.9500 . ?
C17 C16 1.403(3) . ?
C17 C19 1.538(9) . ?
C17 C27 1.411(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.397(3) . ?
C16 H16 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.372(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(3) . ?
C2 H2 0.9500 . ?
C19 C20 1.406(8) . ?
C19 C18 1.436(10) . ?
C20 H20 0.9500 . ?
C20 N3 1.365(7) . ?
C18 H18 0.9500 . ?
C18 C24 1.387(8) . ?
N3 C23 1.337(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(6) . ?
C24 H24 0.9500 . ?
N2 C26 1.337(10) . ?
N2 C30 1.350(10) . ?
C29 H29 0.9500 . ?
C29 C28 1.364(13) . ?
C29 C30 1.348(11) . ?
C26 H26 0.9500 . ?
C26 C27 1.345(15) . ?
C28 H28 0.9500 . ?
C28 C27 1.353(14) . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.88(19) . . ?
C11 C10 C12 128.51(16) . . ?
C11 C10 C9 122.93(17) . . ?
C9 C10 C12 108.56(17) . . ?
O1 C12 C10 126.92(17) . . ?
O1 C12 C13 127.34(17) . . ?
C13 C12 C10 105.74(14) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C6 119.18(16) . . ?
C6 C11 H11 120.4 . . ?
C10 C9 C14 108.80(16) . . ?
C8 C9 C10 118.54(19) . . ?
C8 C9 C14 132.66(17) . . ?
C14 C13 C12 108.51(17) . . ?
C22 C13 C12 128.98(16) . . ?
C22 C13 C14 122.50(18) . . ?
C11 C6 C4 120.94(17) . . ?
C7 C6 C11 117.44(18) . . ?
C7 C6 C4 121.61(17) . . ?
C13 C14 C9 108.39(16) . . ?
C15 C14 C9 133.07(19) . . ?
C15 C14 C13 118.5(2) . . ?
C5 C4 C6 121.38(17) . . ?
C3 C4 C6 123.02(18) . . ?
C3 C4 C5 115.59(19) . . ?
C13 C22 H22 120.2 . . ?
C13 C22 C17 119.58(18) . . ?
C17 C22 H22 120.2 . . ?
C9 C8 H8 120.6 . . ?
C7 C8 C9 118.83(17) . . ?
C7 C8 H8 120.6 . . ?
C6 C7 H7 118.5 . . ?
C8 C7 C6 123.07(17) . . ?
C8 C7 H7 118.5 . . ?
N1 C5 C4 125.20(18) . . ?
N1 C5 H5 117.4 . . ?
C4 C5 H5 117.4 . . ?
C22 C17 C19 116.1(4) . . ?
C22 C17 C27 128.5(6) . . ?
C16 C17 C22 117.7(2) . . ?
C16 C17 C19 126.2(4) . . ?
C16 C17 C27 113.8(6) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C17 C16 H16 118.8 . . ?
C15 C16 C17 122.47(19) . . ?
C15 C16 H16 118.8 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 122.9(2) . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.96(19) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C20 C19 C17 125.2(7) . . ?
C20 C19 C18 113.1(6) . . ?
C18 C19 C17 121.7(6) . . ?
C19 C20 H20 116.9 . . ?
N3 C20 C19 126.3(6) . . ?
N3 C20 H20 116.9 . . ?
C19 C18 H18 119.1 . . ?
C24 C18 C19 121.8(5) . . ?
C24 C18 H18 119.1 . . ?
C23 N3 C20 117.3(4) . . ?
N3 C23 H23 118.5 . . ?
N3 C23 C24 123.0(5) . . ?
C24 C23 H23 118.5 . . ?
C18 C24 C23 118.6(6) . . ?
C18 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C26 N2 C30 117.0(7) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C30 C29 C28 119.8(8) . . ?
N2 C26 H26 119.8 . . ?
N2 C26 C27 120.4(8) . . ?
C27 C26 H26 119.8 . . ?
C29 C28 H28 121.9 . . ?
C27 C28 C29 116.1(9) . . ?
C27 C28 H28 121.9 . . ?
C26 C27 C17 122.2(10) . . ?
C26 C27 C28 123.4(11) . . ?
C28 C27 C17 114.3(11) . . ?
N2 C30 H30 118.4 . . ?
C29 C30 N2 123.2(9) . . ?
C29 C30 H30 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C13 C14 -179.81(17) . . . . ?
O1 C12 C13 C22 0.5(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C10 C12 C13 C14 0.42(18) . . . . ?
C10 C12 C13 C22 -179.27(17) . . . . ?
C10 C11 C6 C4 179.58(15) . . . . ?
C10 C11 C6 C7 -0.6(2) . . . . ?
C10 C9 C14 C13 0.0(2) . . . . ?
C10 C9 C14 C15 179.67(18) . . . . ?
C10 C9 C8 C7 -0.9(3) . . . . ?
C12 C10 C11 C6 -179.15(16) . . . . ?
C12 C10 C9 C14 0.24(19) . . . . ?
C12 C10 C9 C8 -179.88(15) . . . . ?
C12 C13 C14 C9 -0.29(19) . . . . ?
C12 C13 C14 C15 -179.99(15) . . . . ?
C12 C13 C22 C17 179.57(16) . . . . ?
C11 C10 C12 O1 -1.1(3) . . . . ?
C11 C10 C12 C13 178.63(16) . . . . ?
C11 C10 C9 C14 -178.87(15) . . . . ?
C11 C10 C9 C8 1.0(3) . . . . ?
C11 C6 C4 C5 20.7(3) . . . . ?
C11 C6 C4 C3 -160.29(19) . . . . ?
C11 C6 C7 C8 0.7(3) . . . . ?
C9 C10 C12 O1 179.83(17) . . . . ?
C9 C10 C12 C13 -0.40(18) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C9 C14 C15 C16 -179.35(18) . . . . ?
C9 C8 C7 C6 0.0(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C13 C22 C17 C16 0.4(3) . . . . ?
C13 C22 C17 C19 178.5(5) . . . . ?
C13 C22 C17 C27 -177.4(9) . . . . ?
C6 C4 C5 N1 178.93(17) . . . . ?
C6 C4 C3 C2 -178.48(18) . . . . ?
C14 C9 C8 C7 178.96(18) . . . . ?
C14 C13 C22 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C4 C6 C7 C8 -179.47(16) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
C22 C13 C14 C9 179.43(16) . . . . ?
C22 C13 C14 C15 -0.3(3) . . . . ?
C22 C17 C16 C15 -0.4(3) . . . . ?
C22 C17 C19 C20 -24.8(10) . . . . ?
C22 C17 C19 C18 156.2(6) . . . . ?
C22 C17 C27 C26 145.9(9) . . . . ?
C22 C17 C27 C28 -31.0(17) . . . . ?
C8 C9 C14 C13 -179.83(18) . . . . ?
C8 C9 C14 C15 -0.2(3) . . . . ?
C7 C6 C4 C5 -159.14(18) . . . . ?
C7 C6 C4 C3 19.9(3) . . . . ?
C5 N1 C1 C2 0.7(3) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C17 C19 C20 N3 179.6(7) . . . . ?
C17 C19 C18 C24 179.3(7) . . . . ?
C16 C17 C19 C20 153.1(6) . . . . ?
C16 C17 C19 C18 -25.9(10) . . . . ?
C16 C17 C27 C26 -32.0(16) . . . . ?
C16 C17 C27 C28 151.1(10) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C19 C17 C16 C15 -178.3(5) . . . . ?
C19 C20 N3 C23 1.2(9) . . . . ?
C19 C18 C24 C23 0.9(9) . . . . ?
C20 C19 C18 C24 0.2(10) . . . . ?
C20 N3 C23 C24 0.1(7) . . . . ?
C18 C19 C20 N3 -1.3(11) . . . . ?
N3 C23 C24 C18 -1.1(8) . . . . ?
N2 C26 C27 C17 -178.6(10) . . . . ?
N2 C26 C27 C28 -2.0(19) . . . . ?
C29 C28 C27 C17 178.8(10) . . . . ?
C29 C28 C27 C26 2(2) . . . . ?
C26 N2 C30 C29 0.5(13) . . . . ?
C28 C29 C30 N2 -0.5(14) . . . . ?
C27 C17 C16 C15 177.7(8) . . . . ?
C30 N2 C26 C27 0.7(13) . . . . ?
C30 C29 C28 C27 -0.8(15) . . . . ?

_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 3.357
_oxdiff_exptl_absorpt_empirical_full_min 0.549
####################################################################### 
# 
# 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_4-DPyFO-P-1
_database_code_depnum_ccdc_archive 'CCDC 2106427'
loop_
_audit_author_name
_audit_author_address
'Yongshen Zheng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H14 N2 O, 2(H O)'
_chemical_formula_sum            'C23 H16 N2 O3'
_chemical_formula_weight         368.38
_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      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                   7.8189(9)
_cell_length_b                   8.8169(10)
_cell_length_c                   14.5550(12)
_cell_angle_alpha                82.988(8)
_cell_angle_beta                 77.869(8)
_cell_angle_gamma                67.346(11)
_cell_volume                     904.37(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7850
_cell_measurement_theta_min      5.4410
_shelx_estimated_absorpt_T_max   0.809
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7777
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.482
_diffrn_reflns_theta_min         3.109
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  88.00   0.50    0.98    --    0.00  77.00-180.00  106
  2  ω    -75.00 -49.00   0.50    0.98    --    0.00 -57.00-180.00   52
  3  ω     -2.00  36.00   0.50    0.98    --    0.00 -57.00 120.00   76
  4  ω    -37.00  12.00   0.50    0.98    --    0.00  77.00-180.00   98
  5  ω    -89.00 -25.00   0.50    0.98    --    0.00 -57.00 120.00  128
  6  ω     11.00  36.00   0.50    0.98    --    0.00 -57.00-180.00   50
  7  ω     34.00  78.00   0.50    3.93    --   98.20 -82.00  30.00   88
  8  ω     10.00 152.00   0.50    3.93    --   98.20 -30.00 -90.00  284
  9  ω     22.00  49.00   0.50    3.93    --   98.20 -82.00 -30.00   54
 10  ω     10.00 134.00   0.50    3.93    --   98.20 -61.00  90.00  248
 11  ω     14.00 117.00   0.50    3.93    --   98.20 -82.00 -90.00  206
 12  ω    100.00 127.00   0.50    3.93    --   98.20 -77.00 120.00   54
 13  ω     59.00 122.00   0.50    3.93    --   98.20  77.00 -90.00  126
 14  ω     87.00 113.00   0.50    3.93    --   98.20 -82.00  30.00   52
 15  ω     76.00 177.00   0.50    3.93    --   98.20   0.00-180.00  202
 16  ω      9.00  45.00   0.50    3.93    --   98.20   0.00-180.00   72
 17  ω     84.00 109.00   0.50    3.93    --   98.20 -82.00-180.00   50
 18  ω     19.00 125.00   0.50    3.93    --   98.20 -82.00  90.00  212
 19  ω     89.00 117.00   0.50    3.93    --   98.20 -82.00 -30.00   56
 20  ω     73.00 153.00   0.50    3.93    --   98.20 -30.00 120.00  160
 21  ω     58.00 133.00   0.50    3.93    --   98.20 -61.00 -90.00  150
 22  ω     79.00 104.00   0.50    3.93    --   98.20 -82.00 150.00   50
 23  ω     23.00  49.00   0.50    3.93    --   98.20 -30.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0676215000
_diffrn_orient_matrix_UB_12      0.1889794000
_diffrn_orient_matrix_UB_13      -0.0110298000
_diffrn_orient_matrix_UB_21      0.0426450000
_diffrn_orient_matrix_UB_22      -0.0104929000
_diffrn_orient_matrix_UB_23      -0.1077986000
_diffrn_orient_matrix_UB_31      -0.2017066000
_diffrn_orient_matrix_UB_32      0.0099621000
_diffrn_orient_matrix_UB_33      0.0016676000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2859
_reflns_number_total             3491
_reflns_odcompleteness_completeness 98.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0913
_refine_ls_restrained_S_all      1.093
_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)+(0.1797P)²+0.2791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2522
_refine_ls_wR_factor_ref         0.2649
_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:
 C3(H3), C15(H15), C2(H2), C1(H1), C8(H8), C16(H16), C21(H21), C19(H19),
 C18(H18), C4(H4), C22(H22), C7(H7), C10(H10), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5439(3) 0.6718(2) 0.62006(14) 0.0419(5) Uani 1 1 d . . . . .
N2 N 1.1941(3) -0.0996(3) 0.89776(17) 0.0398(6) Uani 1 1 d . . . . .
N1 N 0.2907(4) 1.1390(3) 0.13400(19) 0.0458(7) Uani 1 1 d . . . . .
O2 O 0.0834(4) 1.4665(3) 0.07591(19) 0.0701(8) Uani 1 1 d . . . . .
O1 O 0.3352(4) 1.6207(3) 0.0320(2) 0.0699(8) Uani 1 1 d . . . . .
C9 C 0.8033(4) 0.4152(3) 0.57324(19) 0.0340(6) Uani 1 1 d . . . . .
C13 C 0.6581(4) 0.6039(3) 0.4551(2) 0.0347(6) Uani 1 1 d . . . . .
C14 C 0.8059(4) 0.4684(3) 0.4122(2) 0.0353(6) Uani 1 1 d . . . . .
C3 C 1.0426(4) 0.1587(4) 0.8197(2) 0.0378(6) Uani 1 1 d . . . . .
H3 H 0.9835 0.2723 0.8231 0.045 Uiso 1 1 calc R . . . .
C12 C 0.6510(4) 0.5784(3) 0.55998(19) 0.0357(6) Uani 1 1 d . . . . .
C5 C 1.0651(4) 0.0825(4) 0.73661(19) 0.0364(7) Uani 1 1 d . . . . .
C20 C 0.4806(4) 0.8707(4) 0.2476(2) 0.0373(7) Uani 1 1 d . . . . .
C11 C 0.8944(4) 0.3529(3) 0.48505(19) 0.0355(6) Uani 1 1 d . . . . .
C17 C 0.5873(4) 0.7294(3) 0.3063(2) 0.0366(7) Uani 1 1 d . . . . .
C15 C 0.8420(4) 0.4646(3) 0.3146(2) 0.0368(6) Uani 1 1 d . . . . .
H15 H 0.9392 0.3762 0.2844 0.044 Uiso 1 1 calc R . . . .
C2 C 1.1088(4) 0.0637(4) 0.8962(2) 0.0396(7) Uani 1 1 d . . . . .
H2 H 1.0930 0.1169 0.9505 0.048 Uiso 1 1 calc R . . . .
C1 C 1.2134(4) -0.1719(4) 0.8190(2) 0.0432(7) Uani 1 1 d . . . . .
H1 H 1.2712 -0.2859 0.8184 0.052 Uiso 1 1 calc R . . . .
C8 C 0.8550(4) 0.3316(3) 0.65592(19) 0.0362(6) Uani 1 1 d . . . . .
H8 H 0.7927 0.3764 0.7139 0.043 Uiso 1 1 calc R . . . .
C16 C 0.7315(4) 0.5942(3) 0.2631(2) 0.0373(7) Uani 1 1 d . . . . .
H16 H 0.7543 0.5908 0.1979 0.045 Uiso 1 1 calc R . . . .
C21 C 0.4354(4) 0.8477(4) 0.1647(2) 0.0397(7) Uani 1 1 d . . . . .
H21 H 0.4677 0.7419 0.1453 0.048 Uiso 1 1 calc R . . . .
C19 C 0.4290(4) 1.0316(4) 0.2722(2) 0.0406(7) Uani 1 1 d . . . . .
H19 H 0.4568 1.0532 0.3272 0.049 Uiso 1 1 calc R . . . .
C18 C 0.5514(4) 0.7330(3) 0.4043(2) 0.0366(7) Uani 1 1 d . . . . .
H18 H 0.4559 0.8224 0.4345 0.044 Uiso 1 1 calc R . . . .
C6 C 1.0034(4) 0.1780(3) 0.6504(2) 0.0361(6) Uani 1 1 d . . . . .
C4 C 1.1530(4) -0.0881(4) 0.7385(2) 0.0402(7) Uani 1 1 d . . . . .
H4 H 1.1709 -0.1454 0.6855 0.048 Uiso 1 1 calc R . . . .
C22 C 0.3420(4) 0.9827(4) 0.1108(2) 0.0436(7) Uani 1 1 d . . . . .
H22 H 0.3130 0.9644 0.0554 0.052 Uiso 1 1 calc R . . . .
C7 C 1.0948(4) 0.1183(4) 0.5619(2) 0.0379(7) Uani 1 1 d . . . . .
H7 H 1.1957 0.0178 0.5582 0.045 Uiso 1 1 calc R . . . .
C10 C 1.0423(4) 0.2017(4) 0.4788(2) 0.0387(7) Uani 1 1 d . . . . .
H10 H 1.1045 0.1574 0.4207 0.046 Uiso 1 1 calc R . . . .
C23 C 0.3362(4) 1.1591(4) 0.2142(2) 0.0437(7) Uani 1 1 d . . . . .
H23 H 0.3029 1.2660 0.2319 0.052 Uiso 1 1 calc R . . . .
H2A H 0.212(4) 1.467(3) 0.056(2) 0.025(7) Uiso 1 1 d . . . . .
H1A H 0.282(8) 1.709(7) -0.022(4) 0.12(2) 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
O3 C12 1.217(3) . ?
N2 C2 1.333(4) . ?
N2 C1 1.332(4) . ?
N1 C22 1.344(4) . ?
N1 C23 1.339(4) . ?
O2 H2A 0.99(3) . ?
O1 H1A 1.06(6) . ?
C9 C12 1.495(4) . ?
C9 C11 1.394(4) . ?
C9 C8 1.383(4) . ?
C13 C14 1.404(4) . ?
C13 C12 1.508(4) . ?
C13 C18 1.365(4) . ?
C14 C11 1.464(4) . ?
C14 C15 1.390(4) . ?
C3 H3 0.9300 . ?
C3 C5 1.401(4) . ?
C3 C2 1.375(4) . ?
C5 C6 1.483(4) . ?
C5 C4 1.392(4) . ?
C20 C17 1.489(4) . ?
C20 C21 1.385(4) . ?
C20 C19 1.388(4) . ?
C11 C10 1.385(4) . ?
C17 C16 1.391(4) . ?
C17 C18 1.397(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C1 C4 1.376(4) . ?
C8 H8 0.9300 . ?
C8 C6 1.402(4) . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.382(4) . ?
C19 H19 0.9300 . ?
C19 C23 1.379(4) . ?
C18 H18 0.9300 . ?
C6 C7 1.391(4) . ?
C4 H4 0.9300 . ?
C22 H22 0.9300 . ?
C7 H7 0.9300 . ?
C7 C10 1.390(4) . ?
C10 H10 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 116.2(3) . . ?
C23 N1 C22 116.0(3) . . ?
C11 C9 C12 108.6(2) . . ?
C8 C9 C12 129.0(3) . . ?
C8 C9 C11 122.4(3) . . ?
C14 C13 C12 107.9(2) . . ?
C18 C13 C14 122.2(3) . . ?
C18 C13 C12 129.9(3) . . ?
C13 C14 C11 109.1(2) . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 C11 132.2(3) . . ?
C5 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C5 119.2(3) . . ?
O3 C12 C9 128.0(3) . . ?
O3 C12 C13 126.9(3) . . ?
C9 C12 C13 105.1(2) . . ?
C3 C5 C6 122.1(3) . . ?
C4 C5 C3 116.3(3) . . ?
C4 C5 C6 121.6(3) . . ?
C21 C20 C17 121.6(3) . . ?
C21 C20 C19 117.3(3) . . ?
C19 C20 C17 121.0(3) . . ?
C9 C11 C14 109.3(2) . . ?
C10 C11 C9 119.5(3) . . ?
C10 C11 C14 131.2(3) . . ?
C16 C17 C20 119.8(3) . . ?
C16 C17 C18 119.0(3) . . ?
C18 C17 C20 121.1(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.4 . . ?
N2 C2 C3 124.4(3) . . ?
N2 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
N2 C1 H1 118.0 . . ?
N2 C1 C4 124.0(3) . . ?
C4 C1 H1 118.0 . . ?
C9 C8 H8 120.8 . . ?
C9 C8 C6 118.5(3) . . ?
C6 C8 H8 120.8 . . ?
C17 C16 H16 119.1 . . ?
C15 C16 C17 121.8(3) . . ?
C15 C16 H16 119.1 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C19 H19 120.4 . . ?
C23 C19 C20 119.2(3) . . ?
C23 C19 H19 120.4 . . ?
C13 C18 C17 119.2(3) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C8 C6 C5 121.0(3) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 C8 118.5(3) . . ?
C5 C4 H4 120.1 . . ?
C1 C4 C5 119.8(3) . . ?
C1 C4 H4 120.1 . . ?
N1 C22 C21 123.6(3) . . ?
N1 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
C6 C7 H7 118.5 . . ?
C10 C7 C6 123.0(3) . . ?
C10 C7 H7 118.5 . . ?
C11 C10 C7 118.0(3) . . ?
C11 C10 H10 121.0 . . ?
C7 C10 H10 121.0 . . ?
N1 C23 C19 124.3(3) . . ?
N1 C23 H23 117.9 . . ?
C19 C23 H23 117.9 . . ?

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
N2 C1 C4 C5 -0.3(4) . . . . ?
C9 C11 C10 C7 -0.5(4) . . . . ?
C9 C8 C6 C5 -179.9(2) . . . . ?
C9 C8 C6 C7 1.4(4) . . . . ?
C13 C14 C11 C9 0.0(3) . . . . ?
C13 C14 C11 C10 179.0(3) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C13 C12 O3 178.3(3) . . . . ?
C14 C13 C12 C9 -1.5(3) . . . . ?
C14 C13 C18 C17 1.3(4) . . . . ?
C14 C11 C10 C7 -179.4(3) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C3 C5 C6 C8 -27.6(4) . . . . ?
C3 C5 C6 C7 151.1(3) . . . . ?
C3 C5 C4 C1 -0.5(4) . . . . ?
C12 C9 C11 C14 -1.0(3) . . . . ?
C12 C9 C11 C10 179.9(3) . . . . ?
C12 C9 C8 C6 179.7(3) . . . . ?
C12 C13 C14 C11 1.0(3) . . . . ?
C12 C13 C14 C15 -179.3(2) . . . . ?
C12 C13 C18 C17 178.9(3) . . . . ?
C5 C3 C2 N2 -0.4(4) . . . . ?
C5 C6 C7 C10 179.5(3) . . . . ?
C20 C17 C16 C15 176.0(2) . . . . ?
C20 C17 C18 C13 -177.1(2) . . . . ?
C20 C21 C22 N1 0.0(4) . . . . ?
C20 C19 C23 N1 0.0(4) . . . . ?
C11 C9 C12 O3 -178.3(3) . . . . ?
C11 C9 C12 C13 1.5(3) . . . . ?
C11 C9 C8 C6 -0.6(4) . . . . ?
C11 C14 C15 C16 179.6(3) . . . . ?
C17 C20 C21 C22 -177.7(2) . . . . ?
C17 C20 C19 C23 177.7(2) . . . . ?
C15 C14 C11 C9 -179.7(3) . . . . ?
C15 C14 C11 C10 -0.7(5) . . . . ?
C2 N2 C1 C4 0.7(4) . . . . ?
C2 C3 C5 C6 -177.7(2) . . . . ?
C2 C3 C5 C4 0.8(4) . . . . ?
C1 N2 C2 C3 -0.4(4) . . . . ?
C8 C9 C12 O3 1.4(5) . . . . ?
C8 C9 C12 C13 -178.7(3) . . . . ?
C8 C9 C11 C14 179.3(2) . . . . ?
C8 C9 C11 C10 0.1(4) . . . . ?
C8 C6 C7 C10 -1.9(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C21 C20 C17 C16 37.5(4) . . . . ?
C21 C20 C17 C18 -145.6(3) . . . . ?
C21 C20 C19 C23 0.2(4) . . . . ?
C19 C20 C17 C16 -139.8(3) . . . . ?
C19 C20 C17 C18 37.1(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C18 C13 C14 C11 179.1(2) . . . . ?
C18 C13 C14 C15 -1.2(4) . . . . ?
C18 C13 C12 O3 0.4(5) . . . . ?
C18 C13 C12 C9 -179.4(3) . . . . ?
C18 C17 C16 C15 -1.0(4) . . . . ?
C6 C5 C4 C1 178.0(2) . . . . ?
C6 C7 C10 C11 1.4(4) . . . . ?
C4 C5 C6 C8 154.1(3) . . . . ?
C4 C5 C6 C7 -27.3(4) . . . . ?
C22 N1 C23 C19 -0.3(4) . . . . ?
C23 N1 C22 C21 0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.811
_oxdiff_exptl_absorpt_empirical_full_min 0.531
####################################################################### 
# 
# 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_4-DPyFO-P21n
_database_code_depnum_ccdc_archive 'CCDC 2106429'
loop_
_audit_author_name
_audit_author_address
'Yongshen Zheng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C H0.61 Cl3, C23 H14 N2 O'
_chemical_formula_sum            'C24 H15 Cl3 N2 O'
_chemical_formula_weight         453.73
_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'
Cl Cl 0.3639 0.7018 '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           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                   13.4267(4)
_cell_length_b                   10.5667(3)
_cell_length_c                   15.7768(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.050(3)
_cell_angle_gamma                90
_cell_volume                     2059.63(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5262
_cell_measurement_temperature    100.10(10)
_cell_measurement_theta_max      72.7620
_cell_measurement_theta_min      3.6930
_shelx_estimated_absorpt_T_max   0.367
_shelx_estimated_absorpt_T_min   0.367
_exptl_absorpt_coefficient_mu    4.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10116
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.530
_diffrn_reflns_theta_min         3.680
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  39.00   0.50    0.88    --    0.00 -77.00  60.00   80
  2  ω    -86.00 -29.00   0.50    0.88    --    0.00 -57.00 120.00  114
  3  ω    -89.00  -6.00   0.50    0.88    --    0.00 -77.00  60.00  166
  4  ω     78.00 185.00   0.50    3.50    --   98.20  45.00-150.00  214
  5  ω     17.00 135.00   0.50    3.50    --   98.20 -77.00   0.00  236
  6  ω     74.00 123.00   0.50    3.50    --   98.20  45.00 -90.00   98
  7  ω     70.00 183.00   0.50    3.50    --   98.20  45.00-120.00  226
  8  ω    132.00 160.00   0.50    3.50    --   98.20  45.00 -90.00   56
  9  ω     76.00 102.00   0.50    3.50    --   98.20  45.00  90.00   52
 10  ω    132.00 187.00   0.50    3.50    --   98.20  45.00  90.00  110
 11  ω     73.00 172.00   0.50    3.50    --   98.20  61.00 150.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1170699000
_diffrn_orient_matrix_UB_12      0.0491212000
_diffrn_orient_matrix_UB_13      0.0325863000
_diffrn_orient_matrix_UB_21      -0.0257819000
_diffrn_orient_matrix_UB_22      0.1032872000
_diffrn_orient_matrix_UB_23      0.0574044000
_diffrn_orient_matrix_UB_31      0.0341538000
_diffrn_orient_matrix_UB_32      -0.0905295000
_diffrn_orient_matrix_UB_33      0.0830499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3488
_reflns_number_total             4028
_reflns_odcompleteness_completeness 99.74
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    ?
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1506P)²+0.4339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.1971
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(Cl3)=1-FVAR(1)
 Sof(Cl4)=FVAR(1)
 Sof(Cl1)=1-FVAR(2)
 Sof(Cl2)=Sof(H24)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C24(H24)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C5(H5), C8(H8), C15(H15), C18(H18), C17(H17),
 C10(H10), C20(H20), C11(H11), C23(H23), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl5 Cl 0.59717(5) 0.05630(8) 0.76122(4) 0.0470(3) Uani 1 1 d . . . . .
Cl4 Cl 0.7712(2) 0.1834(5) 0.73449(10) 0.0640(10) Uani 0.692(11) 1 d . . P A 1
Cl2 Cl 0.6922(4) -0.04909(16) 0.6410(3) 0.0669(10) Uani 0.605(8) 1 d . . P A 1
O1 O 0.01237(12) 0.79769(15) 0.34971(11) 0.0307(4) Uani 1 1 d . . . . .
N1 N -0.22701(15) 1.49419(19) 0.27925(14) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.48307(17) 0.3036(2) 0.58723(15) 0.0389(5) Uani 1 1 d . . . . .
C9 C -0.06653(17) 1.3102(2) 0.37012(15) 0.0257(5) Uani 1 1 d . . . . .
C2 C 0.07861(16) 0.9970(2) 0.43033(15) 0.0261(5) Uani 1 1 d . . . . .
C3 C -0.00114(16) 1.0851(2) 0.38716(15) 0.0254(5) Uani 1 1 d . . . . .
H3 H -0.0671 1.0604 0.3391 0.030 Uiso 1 1 calc R . . . .
C13 C 0.24382(17) 0.9137(2) 0.53280(16) 0.0275(5) Uani 1 1 d . . . . .
C12 C 0.17648(16) 1.0291(2) 0.50318(15) 0.0266(5) Uani 1 1 d . . . . .
C14 C 0.18765(17) 0.8123(2) 0.47728(15) 0.0268(5) Uani 1 1 d . . . . .
C6 C -0.24702(18) 1.3697(2) 0.26883(16) 0.0305(5) Uani 1 1 d . . . . .
H6 H -0.3180 1.3437 0.2298 0.037 Uiso 1 1 calc R . . . .
C7 C -0.12600(19) 1.5265(2) 0.33590(17) 0.0312(5) Uani 1 1 d . . . . .
H7 H -0.1087 1.6140 0.3447 0.037 Uiso 1 1 calc R . . . .
C5 C -0.17161(17) 1.2764(2) 0.31087(16) 0.0286(5) Uani 1 1 d . . . . .
H5 H -0.1910 1.1897 0.2996 0.034 Uiso 1 1 calc R . . . .
C8 C -0.04580(18) 1.4402(2) 0.38210(17) 0.0287(5) Uani 1 1 d . . . . .
H8 H 0.0237 1.4692 0.4222 0.034 Uiso 1 1 calc R . . . .
C15 C 0.23187(17) 0.6925(2) 0.48629(15) 0.0279(5) Uani 1 1 d . . . . .
H15 H 0.1928 0.6255 0.4472 0.033 Uiso 1 1 calc R . . . .
C4 C 0.01714(16) 1.2123(2) 0.41573(15) 0.0259(5) Uani 1 1 d . . . . .
C1 C 0.08100(16) 0.8592(2) 0.40991(15) 0.0264(5) Uani 1 1 d . . . . .
C18 C 0.34608(17) 0.8942(2) 0.60030(16) 0.0302(5) Uani 1 1 d . . . . .
H18 H 0.3850 0.9617 0.6389 0.036 Uiso 1 1 calc R . . . .
C16 C 0.33560(17) 0.6716(2) 0.55436(15) 0.0287(5) Uani 1 1 d . . . . .
C17 C 0.39059(17) 0.7731(2) 0.61028(16) 0.0310(5) Uani 1 1 d . . . . .
H17 H 0.4606 0.7589 0.6566 0.037 Uiso 1 1 calc R . . . .
C10 C 0.11591(17) 1.2437(2) 0.48733(16) 0.0294(5) Uani 1 1 d . . . . .
H10 H 0.1290 1.3295 0.5065 0.035 Uiso 1 1 calc R . . . .
C20 C 0.36570(18) 0.4637(2) 0.49079(17) 0.0325(5) Uani 1 1 d . . . . .
H20 H 0.3181 0.4887 0.4307 0.039 Uiso 1 1 calc R . . . .
C11 C 0.19552(17) 1.1539(2) 0.53145(16) 0.0301(5) Uani 1 1 d . . . . .
H11 H 0.2615 1.1779 0.5799 0.036 Uiso 1 1 calc R . . . .
C19 C 0.38535(17) 0.5445(2) 0.56574(17) 0.0297(5) Uani 1 1 d . . . . .
C23 C 0.45491(19) 0.5001(3) 0.65201(17) 0.0348(5) Uani 1 1 d . . . . .
H23 H 0.4707 0.5510 0.7053 0.042 Uiso 1 1 calc R . . . .
C21 C 0.41599(19) 0.3471(2) 0.50486(17) 0.0361(5) Uani 1 1 d . . . . .
H21 H 0.4022 0.2943 0.4527 0.043 Uiso 1 1 calc R . . . .
C24 C 0.6545(2) 0.0889(3) 0.68053(18) 0.0367(6) Uani 1 1 d . . . . .
H24 H 0.6009 0.1362 0.6272 0.044 Uiso 0.605(8) 1 calc R . P A 1
C22 C 0.5007(2) 0.3811(3) 0.65910(18) 0.0399(6) Uani 1 1 d . . . . .
H22 H 0.5475 0.3526 0.7185 0.048 Uiso 1 1 calc R . . . .
Cl3 Cl 0.7923(3) 0.1076(12) 0.7327(2) 0.058(2) Uani 0.308(11) 1 d . . P A 2
Cl1 Cl 0.6258(5) -0.0382(3) 0.5999(3) 0.0576(15) Uani 0.395(8) 1 d . . P A 2


_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
Cl5 C24 1.760(3) . ?
Cl4 C24 1.770(3) . ?
Cl2 C24 1.738(3) . ?
O1 C1 1.220(3) . ?
N1 C6 1.340(3) . ?
N1 C7 1.344(3) . ?
N2 C21 1.340(3) . ?
N2 C22 1.343(4) . ?
C9 C5 1.400(3) . ?
C9 C8 1.399(3) . ?
C9 C4 1.489(3) . ?
C2 C3 1.381(3) . ?
C2 C12 1.407(3) . ?
C2 C1 1.494(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(3) . ?
C13 C12 1.481(3) . ?
C13 C14 1.402(3) . ?
C13 C18 1.385(3) . ?
C12 C11 1.383(3) . ?
C14 C15 1.382(3) . ?
C14 C1 1.495(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.382(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(3) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.404(3) . ?
C4 C10 1.404(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.395(3) . ?
C16 C17 1.401(3) . ?
C16 C19 1.479(3) . ?
C17 H17 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.395(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.398(4) . ?
C20 C21 1.380(3) . ?
C11 H11 0.9500 . ?
C19 C23 1.396(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.385(4) . ?
C21 H21 0.9500 . ?
C24 H24 1.0000 . ?
C24 Cl3 1.717(4) . ?
C24 Cl1 1.786(3) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 115.6(2) . . ?
C21 N2 C22 116.0(2) . . ?
C5 C9 C4 121.2(2) . . ?
C8 C9 C5 115.8(2) . . ?
C8 C9 C4 123.0(2) . . ?
C3 C2 C12 122.4(2) . . ?
C3 C2 C1 128.97(19) . . ?
C12 C2 C1 108.63(18) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.78(19) . . ?
C4 C3 H3 120.6 . . ?
C14 C13 C12 108.64(19) . . ?
C18 C13 C12 131.6(2) . . ?
C18 C13 C14 119.7(2) . . ?
C2 C12 C13 108.56(19) . . ?
C11 C12 C2 119.3(2) . . ?
C11 C12 C13 132.1(2) . . ?
C13 C14 C1 108.80(19) . . ?
C15 C14 C13 122.1(2) . . ?
C15 C14 C1 129.1(2) . . ?
N1 C6 H6 117.7 . . ?
N1 C6 C5 124.5(2) . . ?
C5 C6 H6 117.7 . . ?
N1 C7 H7 118.0 . . ?
N1 C7 C8 124.0(2) . . ?
C8 C7 H7 118.0 . . ?
C9 C5 H5 120.1 . . ?
C6 C5 C9 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.7(2) . . ?
C16 C15 H15 120.6 . . ?
C3 C4 C9 120.29(19) . . ?
C10 C4 C9 121.4(2) . . ?
C10 C4 C3 118.3(2) . . ?
O1 C1 C2 127.8(2) . . ?
O1 C1 C14 126.8(2) . . ?
C2 C1 C14 105.37(17) . . ?
C13 C18 H18 120.8 . . ?
C13 C18 C17 118.4(2) . . ?
C17 C18 H18 120.8 . . ?
C15 C16 C19 120.1(2) . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 C19 121.1(2) . . ?
C18 C17 C16 122.3(2) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C4 C10 H10 118.7 . . ?
C11 C10 C4 122.6(2) . . ?
C11 C10 H10 118.7 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C21 C20 C19 119.4(2) . . ?
C12 C11 C10 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C20 C19 C16 121.7(2) . . ?
C23 C19 C16 121.4(2) . . ?
C23 C19 C20 116.9(2) . . ?
C19 C23 H23 120.3 . . ?
C22 C23 C19 119.4(2) . . ?
C22 C23 H23 120.3 . . ?
N2 C21 C20 124.3(2) . . ?
N2 C21 H21 117.9 . . ?
C20 C21 H21 117.9 . . ?
Cl5 C24 Cl4 108.54(15) . . ?
Cl5 C24 H24 109.4 . . ?
Cl5 C24 Cl1 109.57(17) . . ?
Cl4 C24 H24 109.4 . . ?
Cl2 C24 Cl5 111.50(16) . . ?
Cl2 C24 Cl4 108.5(3) . . ?
Cl2 C24 H24 109.4 . . ?
Cl3 C24 Cl5 111.71(17) . . ?
Cl3 C24 Cl1 108.6(4) . . ?
N2 C22 C23 124.1(2) . . ?
N2 C22 H22 118.0 . . ?
C23 C22 H22 118.0 . . ?

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
N1 C6 C5 C9 1.1(4) . . . . ?
N1 C7 C8 C9 1.2(4) . . . . ?
C9 C4 C10 C11 179.8(2) . . . . ?
C2 C3 C4 C9 179.37(19) . . . . ?
C2 C3 C4 C10 -0.2(3) . . . . ?
C2 C12 C11 C10 0.9(3) . . . . ?
C3 C2 C12 C13 -179.41(19) . . . . ?
C3 C2 C12 C11 -1.8(3) . . . . ?
C3 C2 C1 O1 0.8(4) . . . . ?
C3 C2 C1 C14 179.0(2) . . . . ?
C3 C4 C10 C11 -0.7(3) . . . . ?
C13 C12 C11 C10 177.8(2) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C13 C14 C1 O1 178.1(2) . . . . ?
C13 C14 C1 C2 -0.1(2) . . . . ?
C13 C18 C17 C16 0.2(4) . . . . ?
C12 C2 C3 C4 1.4(3) . . . . ?
C12 C2 C1 O1 -177.6(2) . . . . ?
C12 C2 C1 C14 0.6(2) . . . . ?
C12 C13 C14 C15 177.6(2) . . . . ?
C12 C13 C14 C1 -0.4(2) . . . . ?
C12 C13 C18 C17 -178.0(2) . . . . ?
C14 C13 C12 C2 0.8(3) . . . . ?
C14 C13 C12 C11 -176.4(2) . . . . ?
C14 C13 C18 C17 0.6(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C19 -179.9(2) . . . . ?
C6 N1 C7 C8 -0.3(3) . . . . ?
C7 N1 C6 C5 -0.8(4) . . . . ?
C5 C9 C8 C7 -0.9(3) . . . . ?
C5 C9 C4 C3 12.0(3) . . . . ?
C5 C9 C4 C10 -168.4(2) . . . . ?
C8 C9 C5 C6 -0.1(3) . . . . ?
C8 C9 C4 C3 -167.0(2) . . . . ?
C8 C9 C4 C10 12.5(3) . . . . ?
C15 C14 C1 O1 0.3(4) . . . . ?
C15 C14 C1 C2 -177.9(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C19 C20 33.1(3) . . . . ?
C15 C16 C19 C23 -147.4(2) . . . . ?
C4 C9 C5 C6 -179.3(2) . . . . ?
C4 C9 C8 C7 178.2(2) . . . . ?
C4 C10 C11 C12 0.3(4) . . . . ?
C1 C2 C3 C4 -176.8(2) . . . . ?
C1 C2 C12 C13 -0.9(2) . . . . ?
C1 C2 C12 C11 176.74(19) . . . . ?
C1 C14 C15 C16 178.7(2) . . . . ?
C18 C13 C12 C2 179.5(2) . . . . ?
C18 C13 C12 C11 2.3(4) . . . . ?
C18 C13 C14 C15 -1.3(3) . . . . ?
C18 C13 C14 C1 -179.2(2) . . . . ?
C16 C19 C23 C22 -179.1(2) . . . . ?
C17 C16 C19 C20 -146.5(2) . . . . ?
C17 C16 C19 C23 33.0(3) . . . . ?
C20 C19 C23 C22 0.4(4) . . . . ?
C19 C16 C17 C18 179.2(2) . . . . ?
C19 C20 C21 N2 0.9(4) . . . . ?
C19 C23 C22 N2 0.3(4) . . . . ?
C21 N2 C22 C23 -0.5(4) . . . . ?
C21 C20 C19 C16 178.6(2) . . . . ?
C21 C20 C19 C23 -0.9(3) . . . . ?
C22 N2 C21 C20 -0.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.991
_oxdiff_exptl_absorpt_empirical_full_min 0.510
####################################################################### 
# 
# 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_3-DPyFO-P212121
_database_code_depnum_ccdc_archive 'CCDC 2106430'
loop_
_audit_author_name
_audit_author_address
'Yongshen Zheng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H14 N2 O'
_chemical_formula_sum            'C23 H14 N2 O'
_chemical_formula_weight         334.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.52570(10)
_cell_length_b                   13.4455(2)
_cell_length_c                   27.9047(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3198.78(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8885
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7950
_cell_measurement_theta_min      3.6470
_shelx_estimated_absorpt_T_max   0.822
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15473
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.117
_diffrn_reflns_theta_min         3.167
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  18.00   0.50    1.13    --    0.00  57.00-150.00   64
  2  ω    -37.00  26.00   0.50    1.13    --    0.00  57.00  90.00  126
  3  ω     31.00  89.00   0.50    1.13    --    0.00  57.00  90.00  116
  4  ω     48.00  74.00   0.50    1.13    --    0.00  57.00-150.00   52
  5  ω     16.00 141.00   0.50    4.52    --   98.80 -82.00   0.00  250
  6  ω     44.00 188.00   0.50    4.52    --   98.80  30.00 -90.00  288
  7  ω     21.00 122.00   0.50    4.52    --   98.80 -82.00-180.00  202
  8  ω    133.00 176.00   0.50    4.52    --   98.80  61.00 -60.00   86
  9  ω     58.00 107.00   0.50    4.52    --   98.80 -82.00 -60.00   98
 10  ω     93.00 139.00   0.50    4.52    --   98.80 -45.00-180.00   92
 11  ω     38.00  67.00   0.50    4.52    --   98.80 -45.00-180.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0273237000
_diffrn_orient_matrix_UB_12      0.0684259000
_diffrn_orient_matrix_UB_13      0.0434772000
_diffrn_orient_matrix_UB_21      -0.0104468000
_diffrn_orient_matrix_UB_22      0.0905090000
_diffrn_orient_matrix_UB_23      -0.0336887000
_diffrn_orient_matrix_UB_31      -0.1783413000
_diffrn_orient_matrix_UB_32      -0.0158615000
_diffrn_orient_matrix_UB_33      -0.0046860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                5905
_reflns_number_total             6296
_reflns_odcompleteness_completeness 99.88
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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         0.156
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.16(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.4325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0827
_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:
 C00F(H00F), C00I(H00I), C00J(H00J), C00M(H00M), C00N(H00N), C00O(H00O),
 C00R(H00R), C00T(H00T), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016),
 C017(H017), C018(H018), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C),
 C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 1.07269(16) 0.72191(12) 0.69883(5) 0.0279(3) Uani 1 1 d . . . . .
O002 O 0.30164(16) 0.51717(12) 0.78421(5) 0.0279(3) Uani 1 1 d . . . . .
N003 N -0.0867(2) 0.59302(14) 0.57419(7) 0.0291(4) Uani 1 1 d . . . . .
N004 N 0.8930(2) 0.52919(14) 0.94718(7) 0.0300(4) Uani 1 1 d . . . . .
N005 N 0.4931(2) 0.70275(15) 0.53342(7) 0.0297(4) Uani 1 1 d . . . . .
N006 N 1.4648(2) 0.67156(15) 0.91094(7) 0.0305(4) Uani 1 1 d . . . . .
C007 C 0.5806(2) 0.49842(15) 0.76837(7) 0.0209(4) Uani 1 1 d . . . . .
C008 C 0.7060(2) 0.75115(15) 0.75587(7) 0.0208(4) Uani 1 1 d . . . . .
C009 C 0.8151(2) 0.75133(15) 0.79695(7) 0.0213(4) Uani 1 1 d . . . . .
C00A C 0.5589(2) 0.74673(15) 0.66549(7) 0.0217(4) Uani 1 1 d . . . . .
C00B C 0.4023(2) 0.49955(15) 0.70285(7) 0.0205(4) Uani 1 1 d . . . . .
C00C C 0.2968(2) 0.50085(15) 0.62308(7) 0.0212(4) Uani 1 1 d . . . . .
C00D C 0.6660(2) 0.48713(15) 0.72576(7) 0.0202(4) Uani 1 1 d . . . . .
C00E C 0.8980(2) 0.49042(15) 0.86233(7) 0.0217(4) Uani 1 1 d . . . . .
C00F C 0.7912(2) 0.76095(15) 0.84596(7) 0.0239(4) Uani 1 1 d . . . . .
H00F H 0.6909 0.7700 0.8583 0.029 Uiso 1 1 calc R . . . .
C00G C 0.8171(2) 0.49178(15) 0.81537(7) 0.0207(4) Uani 1 1 d . . . . .
C00H C 0.4109(2) 0.50620(15) 0.75628(7) 0.0215(4) Uani 1 1 d . . . . .
C00I C 0.9204(2) 0.75673(15) 0.87621(7) 0.0235(4) Uani 1 1 d . . . . .
H00I H 0.9048 0.7635 0.9090 0.028 Uiso 1 1 calc R . . . .
C00J C 0.0370(2) 0.57479(16) 0.60224(8) 0.0256(4) Uani 1 1 d . . . . .
H00J H 0.0391 0.6047 0.6323 0.031 Uiso 1 1 calc R . . . .
C00K C 0.5553(2) 0.48700(15) 0.68504(7) 0.0204(4) Uani 1 1 d . . . . .
C00L C 0.9621(2) 0.73237(15) 0.72636(7) 0.0218(4) Uani 1 1 d . . . . .
C00M C 0.7227(2) 0.73906(15) 0.66878(7) 0.0213(4) Uani 1 1 d . . . . .
H00M H 0.7834 0.7328 0.6413 0.026 Uiso 1 1 calc R . . . .
C00N C 0.5439(2) 0.75756(15) 0.75297(8) 0.0228(4) Uani 1 1 d . . . . .
H00N H 0.4837 0.7638 0.7806 0.027 Uiso 1 1 calc R . . . .
C00O C 0.4725(2) 0.75455(15) 0.70813(7) 0.0233(4) Uani 1 1 d . . . . .
H00O H 0.3637 0.7578 0.7064 0.028 Uiso 1 1 calc R . . . .
C00P C 1.0735(2) 0.74263(15) 0.85915(7) 0.0219(4) Uani 1 1 d . . . . .
C00Q C 0.9682(2) 0.73816(15) 0.77968(7) 0.0213(4) Uani 1 1 d . . . . .
C00R C 0.3243(2) 0.77640(16) 0.61155(8) 0.0252(4) Uani 1 1 d . . . . .
H00R H 0.2673 0.8010 0.6374 0.030 Uiso 1 1 calc R . . . .
C00S C 0.4792(2) 0.74507(15) 0.61780(7) 0.0218(4) Uani 1 1 d . . . . .
C00T C 0.8285(3) 0.53061(15) 0.90335(7) 0.0250(4) Uani 1 1 d . . . . .
H00T H 0.7306 0.5604 0.9000 0.030 Uiso 1 1 calc R . . . .
C00U C 0.7926(2) 0.74096(15) 0.71345(7) 0.0212(4) Uani 1 1 d . . . . .
C00V C 1.2085(2) 0.73904(16) 0.89248(7) 0.0231(4) Uani 1 1 d . . . . .
C00W C 0.6529(2) 0.50026(15) 0.81270(7) 0.0210(4) Uani 1 1 d . . . . .
H00W H 0.5935 0.5070 0.8405 0.025 Uiso 1 1 calc R . . . .
C00X C 0.2747(2) 0.50698(15) 0.67297(7) 0.0219(4) Uani 1 1 d . . . . .
H00X H 0.1747 0.5160 0.6856 0.026 Uiso 1 1 calc R . . . .
C00Y C 0.9014(2) 0.48248(15) 0.77236(7) 0.0226(4) Uani 1 1 d . . . . .
H00Y H 1.0102 0.4782 0.7737 0.027 Uiso 1 1 calc R . . . .
C00Z C 0.5789(2) 0.47895(16) 0.63616(7) 0.0231(4) Uani 1 1 d . . . . .
H00Z H 0.6789 0.4692 0.6237 0.028 Uiso 1 1 calc R . . . .
C010 C 0.1634(2) 0.51409(15) 0.58969(7) 0.0219(4) Uani 1 1 d . . . . .
C011 C 1.0959(2) 0.73310(15) 0.80960(7) 0.0219(4) Uani 1 1 d . . . . .
H011 H 1.1959 0.7235 0.7971 0.026 Uiso 1 1 calc R . . . .
C012 C 0.8279(2) 0.47942(16) 0.72778(7) 0.0230(4) Uani 1 1 d . . . . .
H012 H 0.8864 0.4723 0.6999 0.028 Uiso 1 1 calc R . . . .
C013 C 0.1587(3) 0.47157(16) 0.54403(7) 0.0250(4) Uani 1 1 d . . . . .
H013 H 0.2391 0.4298 0.5339 0.030 Uiso 1 1 calc R . . . .
C014 C 1.3358(2) 0.67592(16) 0.88355(7) 0.0256(4) Uani 1 1 d . . . . .
H014 H 1.3305 0.6344 0.8569 0.031 Uiso 1 1 calc R . . . .
C015 C 0.2566(2) 0.77049(16) 0.56664(8) 0.0269(5) Uani 1 1 d . . . . .
H015 H 0.1538 0.7913 0.5619 0.032 Uiso 1 1 calc R . . . .
C016 C 0.3438(3) 0.73332(17) 0.52891(8) 0.0277(5) Uani 1 1 d . . . . .
H016 H 0.2968 0.7293 0.4989 0.033 Uiso 1 1 calc R . . . .
C017 C 0.4492(2) 0.48584(15) 0.60598(7) 0.0230(4) Uani 1 1 d . . . . .
H017 H 0.4645 0.4802 0.5731 0.028 Uiso 1 1 calc R . . . .
C018 C 1.0463(2) 0.44806(16) 0.86791(8) 0.0255(4) Uani 1 1 d . . . . .
H018 H 1.0987 0.4215 0.8416 0.031 Uiso 1 1 calc R . . . .
C019 C -0.0874(3) 0.55173(17) 0.53056(8) 0.0289(5) Uani 1 1 d . . . . .
H019 H -0.1726 0.5636 0.5106 0.035 Uiso 1 1 calc R . . . .
C01A C 0.5570(2) 0.70944(16) 0.57723(7) 0.0259(4) Uani 1 1 d . . . . .
H01A H 0.6605 0.6889 0.5808 0.031 Uiso 1 1 calc R . . . .
C01B C 1.2167(3) 0.79888(16) 0.93295(7) 0.0273(5) Uani 1 1 d . . . . .
H01B H 1.1340 0.8410 0.9406 0.033 Uiso 1 1 calc R . . . .
C01C C 1.4692(3) 0.73217(18) 0.94930(8) 0.0316(5) Uani 1 1 d . . . . .
H01C H 1.5585 0.7313 0.9684 0.038 Uiso 1 1 calc R . . . .
C01D C 0.0334(3) 0.49209(17) 0.51393(8) 0.0291(5) Uani 1 1 d . . . . .
H01D H 0.0306 0.4662 0.4830 0.035 Uiso 1 1 calc R . . . .
C01E C 1.0339(3) 0.48571(18) 0.95115(8) 0.0312(5) Uani 1 1 d . . . . .
H01E H 1.0795 0.4822 0.9814 0.037 Uiso 1 1 calc R . . . .
C01F C 1.3488(3) 0.79555(18) 0.96189(8) 0.0312(5) Uani 1 1 d . . . . .
H01F H 1.3561 0.8351 0.9891 0.037 Uiso 1 1 calc R . . . .
C01G C 1.1149(3) 0.44583(18) 0.91287(8) 0.0303(5) Uani 1 1 d . . . . .
H01G H 1.2138 0.4180 0.9172 0.036 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
O001 C00L 1.225(2) . ?
O002 C00H 1.223(2) . ?
N003 C00J 1.336(3) . ?
N003 C019 1.338(3) . ?
N004 C00T 1.341(3) . ?
N004 C01E 1.340(3) . ?
N005 C016 1.343(3) . ?
N005 C01A 1.342(3) . ?
N006 C014 1.340(3) . ?
N006 C01C 1.346(3) . ?
C007 C00D 1.403(3) . ?
C007 C00H 1.489(3) . ?
C007 C00W 1.382(3) . ?
C008 C009 1.476(3) . ?
C008 C00N 1.387(3) . ?
C008 C00U 1.402(3) . ?
C009 C00F 1.389(3) . ?
C009 C00Q 1.402(3) . ?
C00A C00M 1.404(3) . ?
C00A C00O 1.403(3) . ?
C00A C00S 1.494(3) . ?
C00B C00H 1.495(3) . ?
C00B C00K 1.406(3) . ?
C00B C00X 1.375(3) . ?
C00C C00X 1.407(3) . ?
C00C C010 1.481(3) . ?
C00C C017 1.399(3) . ?
C00D C00K 1.477(3) . ?
C00D C012 1.385(3) . ?
C00E C00G 1.481(3) . ?
C00E C00T 1.398(3) . ?
C00E C018 1.395(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.389(3) . ?
C00G C00W 1.407(3) . ?
C00G C00Y 1.404(3) . ?
C00I H00I 0.9300 . ?
C00I C00P 1.403(3) . ?
C00J H00J 0.9300 . ?
C00J C010 1.396(3) . ?
C00K C00Z 1.383(3) . ?
C00L C00Q 1.491(3) . ?
C00L C00U 1.493(3) . ?
C00M H00M 0.9300 . ?
C00M C00U 1.382(3) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.392(3) . ?
C00O H00O 0.9300 . ?
C00P C00V 1.480(3) . ?
C00P C011 1.402(3) . ?
C00Q C011 1.373(3) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.397(3) . ?
C00R C015 1.382(3) . ?
C00S C01A 1.397(3) . ?
C00T H00T 0.9300 . ?
C00V C014 1.400(3) . ?
C00V C01B 1.388(3) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C012 1.394(3) . ?
C00Z H00Z 0.9300 . ?
C00Z C017 1.393(3) . ?
C010 C013 1.397(3) . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C01D 1.386(3) . ?
C014 H014 0.9300 . ?
C015 H015 0.9300 . ?
C015 C016 1.382(3) . ?
C016 H016 0.9300 . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C018 C01G 1.385(3) . ?
C019 H019 0.9300 . ?
C019 C01D 1.385(3) . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9300 . ?
C01B C01F 1.386(3) . ?
C01C H01C 0.9300 . ?
C01C C01F 1.379(3) . ?
C01D H01D 0.9300 . ?
C01E H01E 0.9300 . ?
C01E C01G 1.381(3) . ?
C01F H01F 0.9300 . ?
C01G H01G 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
C00J N003 C019 117.4(2) . . ?
C01E N004 C00T 116.69(19) . . ?
C01A N005 C016 116.74(19) . . ?
C014 N006 C01C 116.7(2) . . ?
C00D C007 C00H 108.67(17) . . ?
C00W C007 C00D 121.94(18) . . ?
C00W C007 C00H 129.39(18) . . ?
C00N C008 C009 132.30(19) . . ?
C00N C008 C00U 118.79(19) . . ?
C00U C008 C009 108.91(17) . . ?
C00F C009 C008 132.25(19) . . ?
C00F C009 C00Q 119.12(19) . . ?
C00Q C009 C008 108.62(17) . . ?
C00M C00A C00S 120.62(18) . . ?
C00O C00A C00M 118.18(19) . . ?
C00O C00A C00S 121.20(17) . . ?
C00K C00B C00H 108.32(17) . . ?
C00X C00B C00H 129.73(18) . . ?
C00X C00B C00K 121.92(18) . . ?
C00X C00C C010 120.83(18) . . ?
C017 C00C C00X 118.05(18) . . ?
C017 C00C C010 121.07(17) . . ?
C007 C00D C00K 108.68(17) . . ?
C012 C00D C007 119.41(19) . . ?
C012 C00D C00K 131.91(19) . . ?
C00T C00E C00G 121.47(18) . . ?
C018 C00E C00G 121.72(18) . . ?
C018 C00E C00T 116.80(19) . . ?
C009 C00F H00F 120.7 . . ?
C00I C00F C009 118.59(19) . . ?
C00I C00F H00F 120.7 . . ?
C00W C00G C00E 120.75(17) . . ?
C00Y C00G C00E 121.10(17) . . ?
C00Y C00G C00W 118.13(18) . . ?
O002 C00H C007 127.15(19) . . ?
O002 C00H C00B 127.23(19) . . ?
C007 C00H C00B 105.61(16) . . ?
C00F C00I H00I 118.8 . . ?
C00F C00I C00P 122.50(18) . . ?
C00P C00I H00I 118.8 . . ?
N003 C00J H00J 117.6 . . ?
N003 C00J C010 124.7(2) . . ?
C010 C00J H00J 117.6 . . ?
C00B C00K C00D 108.71(17) . . ?
C00Z C00K C00B 119.55(18) . . ?
C00Z C00K C00D 131.73(18) . . ?
O001 C00L C00Q 127.22(19) . . ?
O001 C00L C00U 127.06(19) . . ?
C00Q C00L C00U 105.72(17) . . ?
C00A C00M H00M 120.4 . . ?
C00U C00M C00A 119.15(19) . . ?
C00U C00M H00M 120.4 . . ?
C008 C00N H00N 120.5 . . ?
C008 C00N C00O 119.09(19) . . ?
C00O C00N H00N 120.5 . . ?
C00A C00O H00O 118.8 . . ?
C00N C00O C00A 122.35(18) . . ?
C00N C00O H00O 118.8 . . ?
C00I C00P C00V 120.98(18) . . ?
C011 C00P C00I 118.28(19) . . ?
C011 C00P C00V 120.74(18) . . ?
C009 C00Q C00L 108.46(17) . . ?
C011 C00Q C009 122.34(18) . . ?
C011 C00Q C00L 129.20(19) . . ?
C00S C00R H00R 120.3 . . ?
C015 C00R H00R 120.3 . . ?
C015 C00R C00S 119.4(2) . . ?
C00R C00S C00A 122.44(19) . . ?
C01A C00S C00A 120.74(18) . . ?
C01A C00S C00R 116.81(19) . . ?
N004 C00T C00E 124.56(19) . . ?
N004 C00T H00T 117.7 . . ?
C00E C00T H00T 117.7 . . ?
C008 C00U C00L 108.26(17) . . ?
C00M C00U C008 122.42(18) . . ?
C00M C00U C00L 129.32(18) . . ?
C014 C00V C00P 120.70(19) . . ?
C01B C00V C00P 122.10(19) . . ?
C01B C00V C014 117.2(2) . . ?
C007 C00W C00G 119.32(18) . . ?
C007 C00W H00W 120.3 . . ?
C00G C00W H00W 120.3 . . ?
C00B C00X C00C 119.32(18) . . ?
C00B C00X H00X 120.3 . . ?
C00C C00X H00X 120.3 . . ?
C00G C00Y H00Y 118.8 . . ?
C012 C00Y C00G 122.34(18) . . ?
C012 C00Y H00Y 118.8 . . ?
C00K C00Z H00Z 120.8 . . ?
C00K C00Z C017 118.39(18) . . ?
C017 C00Z H00Z 120.8 . . ?
C00J C010 C00C 120.34(18) . . ?
C00J C010 C013 116.48(19) . . ?
C013 C010 C00C 123.12(19) . . ?
C00P C011 H011 120.4 . . ?
C00Q C011 C00P 119.17(19) . . ?
C00Q C011 H011 120.4 . . ?
C00D C012 C00Y 118.85(19) . . ?
C00D C012 H012 120.6 . . ?
C00Y C012 H012 120.6 . . ?
C010 C013 H013 120.2 . . ?
C01D C013 C010 119.5(2) . . ?
C01D C013 H013 120.2 . . ?
N006 C014 C00V 124.1(2) . . ?
N006 C014 H014 117.9 . . ?
C00V C014 H014 117.9 . . ?
C00R C015 H015 120.4 . . ?
C00R C015 C016 119.13(19) . . ?
C016 C015 H015 120.4 . . ?
N005 C016 C015 123.3(2) . . ?
N005 C016 H016 118.4 . . ?
C015 C016 H016 118.4 . . ?
C00C C017 H017 118.6 . . ?
C00Z C017 C00C 122.73(18) . . ?
C00Z C017 H017 118.6 . . ?
C00E C018 H018 120.2 . . ?
C01G C018 C00E 119.5(2) . . ?
C01G C018 H018 120.2 . . ?
N003 C019 H019 118.6 . . ?
N003 C019 C01D 122.8(2) . . ?
C01D C019 H019 118.6 . . ?
N005 C01A C00S 124.64(19) . . ?
N005 C01A H01A 117.7 . . ?
C00S C01A H01A 117.7 . . ?
C00V C01B H01B 120.1 . . ?
C01F C01B C00V 119.7(2) . . ?
C01F C01B H01B 120.1 . . ?
N006 C01C H01C 118.1 . . ?
N006 C01C C01F 123.8(2) . . ?
C01F C01C H01C 118.1 . . ?
C013 C01D H01D 120.5 . . ?
C019 C01D C013 119.0(2) . . ?
C019 C01D H01D 120.5 . . ?
N004 C01E H01E 118.2 . . ?
N004 C01E C01G 123.6(2) . . ?
C01G C01E H01E 118.2 . . ?
C01B C01F H01F 120.8 . . ?
C01C C01F C01B 118.4(2) . . ?
C01C C01F H01F 120.8 . . ?
C018 C01G H01G 120.6 . . ?
C01E C01G C018 118.8(2) . . ?
C01E C01G H01G 120.6 . . ?

_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.918
####################################################################### 
# 
# 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_3-DPyFO-P-1
_database_code_depnum_ccdc_archive 'CCDC 2106425'
loop_
_audit_author_name
_audit_author_address
'Yongshen Zheng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C23 H14 N2 O), 2(H2 O), C4 H'
_chemical_formula_sum            'C50 H35 N4 O4'
_chemical_formula_weight         755.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.51360(10)
_cell_length_b                   13.5667(2)
_cell_length_c                   15.9278(3)
_cell_angle_alpha                88.4140(10)
_cell_angle_beta                 84.0860(10)
_cell_angle_gamma                81.0860(10)
_cell_volume                     1807.66(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10022
_cell_measurement_temperature    99.96(10)
_cell_measurement_theta_max      72.9020
_cell_measurement_theta_min      4.3350
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             790
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18640
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.226
_diffrn_reflns_theta_min         1.284
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  89.00   0.50    1.18    --    0.00  57.00 -90.00   68
  2  ω    -37.00  16.00   0.50    1.18    --    0.00  57.00-150.00  106
  3  ω     38.00  78.00   0.50    1.18    --    0.00  57.00-150.00   80
  4  ω      2.00  40.00   0.50    1.18    --    0.00 -77.00-150.00   76
  5  ω    -89.00 -34.00   0.50    1.18    --    0.00 -77.00-150.00  110
  6  ω     55.00  89.00   0.50    1.18    --    0.00  57.00-120.00   68
  7  ω    -10.00  39.00   0.50    1.18    --    0.00  57.00 -90.00   98
  8  ω     84.00 133.00   0.50   11.50    --   98.20 -82.00-120.00   98
  9  ω     49.00  81.00   0.50   11.50    --   98.20 -61.00 -30.00   64
 10  ω     21.00 136.00   0.50   11.50    --   98.20 -82.00 -60.00  230
 11  ω     94.00 140.00   0.50   11.50    --   98.20 -82.00-180.00   92
 12  ω    100.00 125.00   0.50   11.50    --   98.20 -61.00 -30.00   50
 13  ω     17.00  43.00   0.50   11.50    --   98.20 -61.00 -30.00   52
 14  ω    115.00 187.00   0.50   11.50    --   98.20  30.00 -30.00  144
 15  ω    130.00 187.00   0.50   11.50    --   98.20  45.00   0.00  114
 16  ω     58.00  83.00   0.50   11.50    --   98.20  45.00  60.00   50
 17  ω     84.00 118.00   0.50   11.50    --   98.20 -82.00   0.00   68
 18  ω     44.00 107.00   0.50   11.50    --   98.20  30.00 -30.00  126
 19  ω     91.00 172.00   0.50   11.50    --   98.20  45.00  60.00  162
 20  ω     79.00 115.00   0.50   11.50    --   98.20 -82.00-150.00   72
 21  ω     23.00  69.00   0.50   11.50    --   98.20 -82.00-150.00   92
 22  ω     11.00  38.00   0.50   11.50    --   98.20 -82.00-180.00   54
 23  ω     12.00 139.00   0.50   11.50    --   98.20 -82.00 120.00  254
 24  ω     63.00 105.00   0.50   11.50    --   98.20 -82.00  60.00   84
 25  ω     18.00  59.00   0.50   11.50    --   98.20 -61.00-150.00   82
 26  ω     69.00 122.00   0.50   11.50    --   98.20  45.00   0.00  106
 27  ω     10.00  88.00   0.50   11.50    --   98.20 -61.00 120.00  156
 28  ω     58.00 165.00   0.50   11.50    --   98.20  45.00  90.00  214
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1287926000
_diffrn_orient_matrix_UB_12      -0.0376865000
_diffrn_orient_matrix_UB_13      0.0594367000
_diffrn_orient_matrix_UB_21      0.1214860000
_diffrn_orient_matrix_UB_22      -0.0300075000
_diffrn_orient_matrix_UB_23      -0.0769435000
_diffrn_orient_matrix_UB_31      0.0504166000
_diffrn_orient_matrix_UB_32      0.1043697000
_diffrn_orient_matrix_UB_33      -0.0019359000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6227
_reflns_number_total             7085
_reflns_odcompleteness_completeness 99.55
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    ?
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         7085
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²+0.9436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1650
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C51) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C52(0.5) C51(0.5) C53(0.5) C50(0.5) C48(0.5) C49(0.5)
4.a Free rotating group:
 O2(H2A,H2B), O4(H4A,H4B)
4.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C29(H29), C6(H6), C38(H38), C15(H15), C32(H32), C17(H17), C28(H28),
 C31(H31), C18(H18), C19(H19), C39(H39), C8(H8), C23(H23), C5(H5), C26(H26),
 C12(H12), C3(H3), C21(H21), C43(H43), C46(H46), C22(H22), C2(H2), C25(H25),
 C45(H45), C1(H1), C24(H24), C44(H44)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69301(14) 0.49004(8) 0.07944(7) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.82402(13) 1.00609(8) 0.92661(7) 0.0219(3) Uani 1 1 d . . . . .
O2 O 0.65159(16) 0.85620(10) 0.49442(9) 0.0354(3) Uani 1 1 d . . . . .
H2A H 0.7284 0.8325 0.4587 0.053 Uiso 1 1 d G . . . .
H2B H 0.6457 0.8102 0.5314 0.053 Uiso 1 1 d G . . . .
O4 O 0.37777(17) 0.95501(11) 0.42333(9) 0.0372(3) Uani 1 1 d . . . . .
H4A H 0.4594 0.9270 0.4461 0.056 Uiso 1 1 d G . . . .
H4B H 0.3456 1.0121 0.4450 0.056 Uiso 1 1 d G . . . .
N4 N 1.04176(17) 1.14671(11) 1.29772(9) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.89520(17) 0.81068(11) 0.36170(9) 0.0271(3) Uani 1 1 d . . . . .
N3 N 0.47157(18) 0.33472(11) -0.28802(9) 0.0280(3) Uani 1 1 d . . . . .
N2 N 0.58344(18) 0.72623(12) 0.63256(9) 0.0299(3) Uani 1 1 d . . . . .
C40 C 0.53371(17) 0.77257(11) 0.86677(10) 0.0172(3) Uani 1 1 d . . . . .
C33 C 0.60687(17) 0.90153(11) 1.09853(10) 0.0167(3) Uani 1 1 d . . . . .
C30 C 0.73413(17) 1.01904(11) 1.20915(9) 0.0170(3) Uani 1 1 d . . . . .
C16 C 0.96746(17) 0.73537(11) 0.13309(10) 0.0184(3) Uani 1 1 d . . . . .
C41 C 0.62931(17) 0.84739(11) 0.87313(10) 0.0174(3) Uani 1 1 d . . . . .
H41 H 0.6814 0.8726 0.8250 0.021 Uiso 1 1 calc R . . . .
C37 C 0.56744(17) 0.84784(11) 1.02597(9) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.88368(17) 0.60484(11) -0.09599(10) 0.0185(3) Uani 1 1 d . . . . .
C10 C 0.76802(17) 0.54029(11) 0.03018(10) 0.0182(3) Uani 1 1 d . . . . .
C14 C 0.85898(17) 0.62061(11) 0.05135(10) 0.0177(3) Uani 1 1 d . . . . .
C35 C 0.74012(17) 0.95985(11) 0.97468(9) 0.0169(3) Uani 1 1 d . . . . .
C36 C 0.64464(17) 0.88275(11) 0.95172(10) 0.0164(3) Uani 1 1 d . . . . .
C7 C 0.75698(17) 0.48340(11) -0.20334(10) 0.0189(3) Uani 1 1 d . . . . .
C29 C 0.77650(17) 1.02538(11) 1.12143(9) 0.0170(3) Uani 1 1 d . . . . .
H29 H 0.8468 1.0680 1.0998 0.020 Uiso 1 1 calc R . . . .
C13 C 0.92738(17) 0.65836(11) -0.02437(10) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.72320(17) 0.47473(11) -0.11534(10) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.6589 0.4293 -0.0923 0.022 Uiso 1 1 calc R . . . .
C42 C 0.51093(18) 0.73317(11) 0.78368(10) 0.0189(3) Uani 1 1 d . . . . .
C34 C 0.71208(17) 0.96752(11) 1.06829(9) 0.0165(3) Uani 1 1 d . . . . .
C38 C 0.47483(18) 0.77297(11) 1.02104(10) 0.0194(3) Uani 1 1 d . . . . .
H38 H 0.4236 0.7480 1.0696 0.023 Uiso 1 1 calc R . . . .
C15 C 0.87762(17) 0.65703(11) 0.12925(10) 0.0185(3) Uani 1 1 d . . . . .
H15 H 0.8315 0.6302 0.1784 0.022 Uiso 1 1 calc R . . . .
C32 C 0.55980(18) 0.89718(12) 1.18419(10) 0.0200(3) Uani 1 1 d . . . . .
H32 H 0.4873 0.8557 1.2053 0.024 Uiso 1 1 calc R . . . .
C27 C 0.81048(18) 1.07301(11) 1.26939(10) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.78719(17) 0.53479(11) -0.06380(10) 0.0177(3) Uani 1 1 d . . . . .
C17 C 1.03413(18) 0.77346(11) 0.05683(10) 0.0196(3) Uani 1 1 d . . . . .
H17 H 1.0923 0.8259 0.0587 0.024 Uiso 1 1 calc R . . . .
C28 C 0.95979(18) 1.10279(12) 1.24612(10) 0.0215(3) Uani 1 1 d . . . . .
H28 H 1.0050 1.0912 1.1909 0.026 Uiso 1 1 calc R . . . .
C20 C 0.99028(18) 0.77839(11) 0.21479(10) 0.0194(3) Uani 1 1 d . . . . .
C31 C 0.62337(18) 0.95639(12) 1.23829(10) 0.0196(3) Uani 1 1 d . . . . .
H31 H 0.5910 0.9542 1.2958 0.024 Uiso 1 1 calc R . . . .
C18 C 1.01617(18) 0.73544(11) -0.02148(10) 0.0199(3) Uani 1 1 d . . . . .
H18 H 1.0629 0.7613 -0.0709 0.024 Uiso 1 1 calc R . . . .
C19 C 1.11520(19) 0.83214(12) 0.22358(10) 0.0217(3) Uani 1 1 d . . . . .
H19 H 1.1895 0.8398 0.1777 0.026 Uiso 1 1 calc R . . . .
C4 C 0.68907(18) 0.42212(11) -0.26153(10) 0.0195(3) Uani 1 1 d . . . . .
C39 C 0.45996(18) 0.73592(11) 0.94184(10) 0.0194(3) Uani 1 1 d . . . . .
H39 H 0.3990 0.6851 0.9386 0.023 Uiso 1 1 calc R . . . .
C8 C 0.85495(19) 0.55273(12) -0.23503(10) 0.0217(3) Uani 1 1 d . . . . .
H8 H 0.8784 0.5583 -0.2931 0.026 Uiso 1 1 calc R . . . .
C23 C 1.1285(2) 0.87385(12) 0.30025(11) 0.0246(3) Uani 1 1 d . . . . .
H23 H 1.2114 0.9095 0.3066 0.030 Uiso 1 1 calc R . . . .
C5 C 0.54074(19) 0.39081(12) -0.23952(10) 0.0221(3) Uani 1 1 d . . . . .
H5 H 0.4866 0.4104 -0.1875 0.026 Uiso 1 1 calc R . . . .
C26 C 0.74532(19) 1.09126(12) 1.35248(10) 0.0229(3) Uani 1 1 d . . . . .
H26 H 0.6458 1.0741 1.3710 0.027 Uiso 1 1 calc R . . . .
C12 C 0.91873(19) 0.61381(12) -0.18250(10) 0.0220(3) Uani 1 1 d . . . . .
H12 H 0.9832 0.6594 -0.2051 0.026 Uiso 1 1 calc R . . . .
C3 C 0.7658(2) 0.39423(12) -0.34091(10) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.8630 0.4146 -0.3595 0.029 Uiso 1 1 calc R . . . .
C21 C 0.88411(19) 0.76996(12) 0.28693(10) 0.0235(3) Uani 1 1 d . . . . .
H21 H 0.8008 0.7340 0.2829 0.028 Uiso 1 1 calc R . . . .
C43 C 0.4014(2) 0.66862(13) 0.77522(11) 0.0293(4) Uani 1 1 d . . . . .
H43 H 0.3381 0.6500 0.8223 0.035 Uiso 1 1 calc R . . . .
C46 C 0.59831(19) 0.75927(14) 0.70957(10) 0.0260(4) Uani 1 1 d . . . . .
H46 H 0.6718 0.8025 0.7139 0.031 Uiso 1 1 calc R . . . .
C22 C 1.0160(2) 0.86156(13) 0.36740(11) 0.0266(4) Uani 1 1 d . . . . .
H22 H 1.0249 0.8900 0.4188 0.032 Uiso 1 1 calc R . . . .
C2 C 0.6958(2) 0.33589(13) -0.39174(11) 0.0305(4) Uani 1 1 d . . . . .
H2 H 0.7457 0.3164 -0.4447 0.037 Uiso 1 1 calc R . . . .
C25 C 0.8296(2) 1.13518(14) 1.40728(11) 0.0293(4) Uani 1 1 d . . . . .
H25 H 0.7882 1.1470 1.4630 0.035 Uiso 1 1 calc R . . . .
C45 C 0.4800(2) 0.66248(14) 0.62709(11) 0.0305(4) Uani 1 1 d . . . . .
H45 H 0.4701 0.6375 0.5744 0.037 Uiso 1 1 calc R . . . .
C1 C 0.5512(2) 0.30700(14) -0.36297(11) 0.0317(4) Uani 1 1 d . . . . .
H1 H 0.5066 0.2664 -0.3971 0.038 Uiso 1 1 calc R . . . .
C24 C 0.9764(2) 1.16106(14) 1.37743(11) 0.0298(4) Uani 1 1 d . . . . .
H24 H 1.0327 1.1899 1.4147 0.036 Uiso 1 1 calc R . . . .
C44 C 0.3873(3) 0.63223(14) 0.69638(12) 0.0361(4) Uani 1 1 d . . . . .
H44 H 0.3163 0.5879 0.6902 0.043 Uiso 1 1 calc R . . . .
C52 C 0.1352(6) 0.4033(5) -0.4910(3) 0.0482(14) Uani 0.5 1 d . . P . .
C51 C 0.2081(8) 0.4620(5) -0.4368(3) 0.0570(16) Uani 0.5 1 d . U P . .
C53 C 0.0003(9) 0.4296(5) -0.5314(4) 0.0274(13) Uani 0.5 1 d . . P . .
C50 C 0.0936(5) 0.5674(4) -0.4305(3) 0.0283(9) Uani 0.5 1 d . . P . .
C48 C -0.0965(5) 0.5265(3) -0.5231(3) 0.0351(10) Uani 0.5 1 d . . P . .
C49 C -0.0535(11) 0.5971(6) -0.4734(7) 0.040(2) Uani 0.5 1 d . . P . .
C47 C -0.2398(19) 0.5472(13) -0.5709(8) 0.322(8) Uani 1 1 d . . . . .
H50 H 0.075(4) 0.602(3) -0.419(2) 0.070(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.2208(19) . ?
O3 C35 1.2205(18) . ?
O2 H2A 0.8505 . ?
O2 H2B 0.8494 . ?
O4 H4A 0.8494 . ?
O4 H4B 0.8506 . ?
N4 C28 1.339(2) . ?
N4 C24 1.339(2) . ?
N1 C21 1.345(2) . ?
N1 C22 1.336(2) . ?
N3 C5 1.337(2) . ?
N3 C1 1.344(2) . ?
N2 C46 1.342(2) . ?
N2 C45 1.337(2) . ?
C40 C41 1.408(2) . ?
C40 C42 1.483(2) . ?
C40 C39 1.407(2) . ?
C33 C37 1.477(2) . ?
C33 C34 1.404(2) . ?
C33 C32 1.384(2) . ?
C30 C29 1.410(2) . ?
C30 C27 1.481(2) . ?
C30 C31 1.401(2) . ?
C16 C15 1.408(2) . ?
C16 C17 1.407(2) . ?
C16 C20 1.484(2) . ?
C41 H41 0.9300 . ?
C41 C36 1.379(2) . ?
C37 C36 1.400(2) . ?
C37 C38 1.387(2) . ?
C11 C13 1.478(2) . ?
C11 C9 1.403(2) . ?
C11 C12 1.386(2) . ?
C10 C14 1.496(2) . ?
C10 C9 1.492(2) . ?
C14 C13 1.403(2) . ?
C14 C15 1.381(2) . ?
C35 C36 1.495(2) . ?
C35 C34 1.489(2) . ?
C7 C6 1.407(2) . ?
C7 C4 1.479(2) . ?
C7 C8 1.402(2) . ?
C29 H29 0.9300 . ?
C29 C34 1.378(2) . ?
C13 C18 1.386(2) . ?
C6 H6 0.9300 . ?
C6 C9 1.379(2) . ?
C42 C43 1.393(2) . ?
C42 C46 1.396(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.396(2) . ?
C15 H15 0.9300 . ?
C32 H32 0.9300 . ?
C32 C31 1.396(2) . ?
C27 C28 1.404(2) . ?
C27 C26 1.394(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(2) . ?
C28 H28 0.9300 . ?
C20 C19 1.400(2) . ?
C20 C21 1.400(2) . ?
C31 H31 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C23 1.382(2) . ?
C4 C5 1.402(2) . ?
C4 C3 1.396(2) . ?
C39 H39 0.9300 . ?
C8 H8 0.9300 . ?
C8 C12 1.397(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.385(2) . ?
C5 H5 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.386(2) . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.385(2) . ?
C21 H21 0.9300 . ?
C43 H43 0.9300 . ?
C43 C44 1.385(2) . ?
C46 H46 0.9300 . ?
C22 H22 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.379(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.385(3) . ?
C45 H45 0.9300 . ?
C45 C44 1.380(3) . ?
C1 H1 0.9300 . ?
C24 H24 0.9300 . ?
C44 H44 0.9300 . ?
C52 C51 1.438(7) . ?
C52 C53 1.369(7) . ?
C52 C48 0.983(7) 2_564 ?
C52 C49 0.943(11) 2_564 ?
C52 C47 1.618(15) 2_564 ?
C51 C50 1.600(9) . ?
C51 C48 1.187(8) 2_564 ?
C51 C47 0.31(2) 2_564 ?
C53 C50 1.047(8) 2_564 ?
C53 C48 1.451(8) 2_564 ?
C53 C48 1.441(8) . ?
C53 C49 0.545(7) 2_564 ?
C50 C53 1.048(8) 2_564 ?
C50 C48 1.485(6) 2_564 ?
C50 C49 1.484(10) . ?
C50 C47 1.836(19) 2_564 ?
C50 H50 0.51(3) . ?
C48 C52 0.983(7) 2_564 ?
C48 C51 1.187(8) 2_564 ?
C48 C53 1.451(8) 2_564 ?
C48 C50 1.485(6) 2_564 ?
C48 C48 1.901(10) 2_564 ?
C48 C49 1.374(12) . ?
C48 C49 1.942(8) 2_564 ?
C48 C47 1.490(16) . ?
C49 C52 0.943(11) 2_564 ?
C49 C53 0.544(7) 2_564 ?
C49 C48 1.942(8) 2_564 ?
C47 C52 1.618(15) 2_564 ?
C47 C51 0.31(2) 2_564 ?
C47 C50 1.836(19) 2_564 ?

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
H2A O2 H2B 104.5 . . ?
H4A O4 H4B 109.5 . . ?
C28 N4 C24 116.88(15) . . ?
C22 N1 C21 117.73(15) . . ?
C5 N3 C1 117.00(15) . . ?
C45 N2 C46 117.45(15) . . ?
C41 C40 C42 121.28(14) . . ?
C39 C40 C41 118.00(14) . . ?
C39 C40 C42 120.71(14) . . ?
C34 C33 C37 108.34(13) . . ?
C32 C33 C37 132.31(14) . . ?
C32 C33 C34 119.34(14) . . ?
C29 C30 C27 121.06(13) . . ?
C31 C30 C29 118.24(14) . . ?
C31 C30 C27 120.63(14) . . ?
C15 C16 C20 121.53(14) . . ?
C17 C16 C15 118.22(14) . . ?
C17 C16 C20 120.24(14) . . ?
C40 C41 H41 120.4 . . ?
C36 C41 C40 119.10(14) . . ?
C36 C41 H41 120.4 . . ?
C36 C37 C33 109.01(13) . . ?
C38 C37 C33 131.88(14) . . ?
C38 C37 C36 119.10(14) . . ?
C9 C11 C13 108.40(13) . . ?
C12 C11 C13 132.13(14) . . ?
C12 C11 C9 119.46(15) . . ?
O1 C10 C14 127.23(14) . . ?
O1 C10 C9 127.14(14) . . ?
C9 C10 C14 105.62(12) . . ?
C13 C14 C10 108.17(13) . . ?
C15 C14 C10 129.45(14) . . ?
C15 C14 C13 122.38(14) . . ?
O3 C35 C36 127.02(14) . . ?
O3 C35 C34 127.49(14) . . ?
C34 C35 C36 105.49(12) . . ?
C41 C36 C37 122.58(14) . . ?
C41 C36 C35 129.04(14) . . ?
C37 C36 C35 108.37(13) . . ?
C6 C7 C4 121.04(14) . . ?
C8 C7 C6 118.52(15) . . ?
C8 C7 C4 120.44(14) . . ?
C30 C29 H29 120.5 . . ?
C34 C29 C30 118.99(14) . . ?
C34 C29 H29 120.5 . . ?
C14 C13 C11 109.09(13) . . ?
C18 C13 C11 131.70(14) . . ?
C18 C13 C14 119.20(14) . . ?
C7 C6 H6 120.6 . . ?
C9 C6 C7 118.82(14) . . ?
C9 C6 H6 120.6 . . ?
C43 C42 C40 122.00(14) . . ?
C43 C42 C46 116.46(15) . . ?
C46 C42 C40 121.53(14) . . ?
C33 C34 C35 108.76(13) . . ?
C29 C34 C33 122.26(14) . . ?
C29 C34 C35 128.96(14) . . ?
C37 C38 H38 120.6 . . ?
C37 C38 C39 118.73(14) . . ?
C39 C38 H38 120.6 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 C16 119.00(14) . . ?
C14 C15 H15 120.5 . . ?
C33 C32 H32 120.7 . . ?
C33 C32 C31 118.63(14) . . ?
C31 C32 H32 120.7 . . ?
C28 C27 C30 120.50(14) . . ?
C26 C27 C30 122.83(14) . . ?
C26 C27 C28 116.55(14) . . ?
C11 C9 C10 108.72(14) . . ?
C6 C9 C11 122.36(14) . . ?
C6 C9 C10 128.92(14) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 C16 122.36(14) . . ?
C18 C17 H17 118.8 . . ?
N4 C28 C27 124.66(15) . . ?
N4 C28 H28 117.7 . . ?
C27 C28 H28 117.7 . . ?
C19 C20 C16 122.20(14) . . ?
C19 C20 C21 116.32(15) . . ?
C21 C20 C16 121.45(14) . . ?
C30 C31 H31 118.8 . . ?
C32 C31 C30 122.44(14) . . ?
C32 C31 H31 118.8 . . ?
C13 C18 C17 118.83(14) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C20 C19 H19 119.9 . . ?
C23 C19 C20 120.17(15) . . ?
C23 C19 H19 119.9 . . ?
C5 C4 C7 120.81(14) . . ?
C3 C4 C7 122.55(14) . . ?
C3 C4 C5 116.63(15) . . ?
C40 C39 H39 118.8 . . ?
C38 C39 C40 122.44(14) . . ?
C38 C39 H39 118.8 . . ?
C7 C8 H8 118.8 . . ?
C12 C8 C7 122.41(15) . . ?
C12 C8 H8 118.8 . . ?
C19 C23 H23 120.6 . . ?
C19 C23 C22 118.70(15) . . ?
C22 C23 H23 120.6 . . ?
N3 C5 C4 124.62(15) . . ?
N3 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C27 C26 H26 120.2 . . ?
C25 C26 C27 119.67(15) . . ?
C25 C26 H26 120.2 . . ?
C11 C12 C8 118.42(14) . . ?
C11 C12 H12 120.8 . . ?
C8 C12 H12 120.8 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.36(15) . . ?
C2 C3 H3 120.3 . . ?
N1 C21 C20 124.07(15) . . ?
N1 C21 H21 118.0 . . ?
C20 C21 H21 118.0 . . ?
C42 C43 H43 120.2 . . ?
C44 C43 C42 119.68(16) . . ?
C44 C43 H43 120.2 . . ?
N2 C46 C42 124.45(16) . . ?
N2 C46 H46 117.8 . . ?
C42 C46 H46 117.8 . . ?
N1 C22 C23 123.00(16) . . ?
N1 C22 H22 118.5 . . ?
C23 C22 H22 118.5 . . ?
C3 C2 H2 120.4 . . ?
C1 C2 C3 119.26(16) . . ?
C1 C2 H2 120.4 . . ?
C26 C25 H25 120.6 . . ?
C24 C25 C26 118.76(16) . . ?
C24 C25 H25 120.6 . . ?
N2 C45 H45 118.7 . . ?
N2 C45 C44 122.70(16) . . ?
C44 C45 H45 118.7 . . ?
N3 C1 C2 123.08(17) . . ?
N3 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
N4 C24 C25 123.46(16) . . ?
N4 C24 H24 118.3 . . ?
C25 C24 H24 118.3 . . ?
C43 C44 H44 120.4 . . ?
C45 C44 C43 119.22(17) . . ?
C45 C44 H44 120.4 . . ?
C51 C52 C47 9.7(9) . 2_564 ?
C53 C52 C51 129.1(7) . . ?
C53 C52 C47 138.8(9) . 2_564 ?
C48 C52 C51 55.0(6) 2_564 . ?
C48 C52 C53 74.2(5) 2_564 . ?
C48 C52 C47 64.6(8) 2_564 2_564 ?
C49 C52 C51 146.0(8) 2_564 . ?
C49 C52 C53 17.2(7) 2_564 . ?
C49 C52 C48 91.1(7) 2_564 2_564 ?
C49 C52 C47 155.6(11) 2_564 2_564 ?
C52 C51 C50 104.9(5) . . ?
C48 C51 C52 42.6(3) 2_564 . ?
C48 C51 C50 62.3(5) 2_564 . ?
C47 C51 C52 120(4) 2_564 . ?
C47 C51 C50 135(3) 2_564 . ?
C47 C51 C48 163(4) 2_564 2_564 ?
C52 C53 C48 122.8(6) . . ?
C52 C53 C48 40.7(3) . 2_564 ?
C50 C53 C52 165.8(8) 2_564 . ?
C50 C53 C48 153.2(8) 2_564 2_564 ?
C50 C53 C48 71.3(6) 2_564 . ?
C48 C53 C48 82.2(5) . 2_564 ?
C49 C53 C52 30.7(16) 2_564 . ?
C49 C53 C50 135(2) 2_564 2_564 ?
C49 C53 C48 71.0(17) 2_564 2_564 ?
C49 C53 C48 153(2) 2_564 . ?
C51 C50 H50 154(4) . . ?
C53 C50 C51 111.9(6) 2_564 . ?
C53 C50 C48 66.8(5) 2_564 2_564 ?
C53 C50 C49 15.0(7) 2_564 . ?
C53 C50 C47 118.8(8) 2_564 2_564 ?
C53 C50 H50 94(4) 2_564 . ?
C48 C50 C51 45.1(3) 2_564 . ?
C48 C50 C47 52.0(5) 2_564 2_564 ?
C48 C50 H50 161(4) 2_564 . ?
C49 C50 C51 126.8(5) . . ?
C49 C50 C48 81.7(4) . 2_564 ?
C49 C50 C47 133.7(6) . 2_564 ?
C49 C50 H50 79(4) . . ?
C47 C50 C51 6.9(5) 2_564 . ?
C47 C50 H50 147(4) 2_564 . ?
C52 C48 C51 82.4(6) 2_564 2_564 ?
C52 C48 C53 162.8(6) 2_564 . ?
C52 C48 C53 65.2(4) 2_564 2_564 ?
C52 C48 C50 154.7(6) 2_564 2_564 ?
C52 C48 C48 113.8(6) 2_564 2_564 ?
C52 C48 C49 155.5(6) 2_564 2_564 ?
C52 C48 C49 43.3(4) 2_564 . ?
C52 C48 C47 78.8(8) 2_564 . ?
C51 C48 C53 147.5(6) 2_564 2_564 ?
C51 C48 C53 114.5(5) 2_564 . ?
C51 C48 C50 72.6(4) 2_564 2_564 ?
C51 C48 C48 163.4(5) 2_564 2_564 ?
C51 C48 C49 121.7(6) 2_564 2_564 ?
C51 C48 C49 125.7(6) 2_564 . ?
C51 C48 C47 3.6(8) 2_564 . ?
C53 C48 C53 97.8(5) . 2_564 ?
C53 C48 C50 41.9(4) . 2_564 ?
C53 C48 C50 139.6(5) 2_564 2_564 ?
C53 C48 C48 49.1(3) . 2_564 ?
C53 C48 C48 48.7(4) 2_564 2_564 ?
C53 C48 C49 7.3(5) . 2_564 ?
C53 C48 C49 90.6(4) 2_564 2_564 ?
C50 C48 C48 91.0(3) 2_564 2_564 ?
C50 C48 C49 49.1(4) 2_564 2_564 ?
C48 C48 C49 41.9(4) 2_564 2_564 ?
C49 C48 C53 119.8(6) . . ?
C49 C48 C53 22.0(3) . 2_564 ?
C49 C48 C50 161.6(5) . 2_564 ?
C49 C48 C48 70.7(4) . 2_564 ?
C49 C48 C49 112.5(4) . 2_564 ?
C47 C48 C53 118.1(8) . . ?
C47 C48 C53 144.0(8) . 2_564 ?
C47 C48 C50 76.2(7) . 2_564 ?
C47 C48 C48 167.1(8) . 2_564 ?
C47 C48 C49 125.3(8) . 2_564 ?
C47 C48 C49 122.1(8) . . ?
C52 C49 C50 162.0(9) 2_564 . ?
C52 C49 C48 45.6(7) 2_564 . ?
C52 C49 C48 112.9(8) 2_564 2_564 ?
C53 C49 C52 132(2) 2_564 2_564 ?
C53 C49 C50 29.9(16) 2_564 . ?
C53 C49 C48 87.0(17) 2_564 . ?
C53 C49 C48 19.7(15) 2_564 2_564 ?
C50 C49 C48 49.2(3) . 2_564 ?
C48 C49 C50 116.6(5) . . ?
C48 C49 C48 67.5(4) . 2_564 ?
C52 C47 C50 88.3(8) 2_564 2_564 ?
C51 C47 C52 50(3) 2_564 2_564 ?
C51 C47 C50 38(3) 2_564 2_564 ?
C51 C47 C48 14(3) 2_564 . ?
C48 C47 C52 36.6(4) . 2_564 ?
C48 C47 C50 51.8(6) . 2_564 ?

_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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.783
####################################################################### 
# 
# 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_4-DPyFO-Fdd2
_database_code_depnum_ccdc_archive 'CCDC 2106428'
loop_
_audit_author_name
_audit_author_address
'Yongshen Zheng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 N2 O'
_chemical_formula_sum            'C23 H14 N2 O'
_chemical_formula_weight         334.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   42.8575(14)
_cell_length_b                   39.7716(17)
_cell_length_c                   3.71790(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6337.2(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    10221
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      72.9520
_cell_measurement_theta_min      3.0620
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2784
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1122
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            15986
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.639
_diffrn_reflns_theta_min         3.032
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  88.00   0.50    1.89    --    0.00  38.00 -90.00  112
  2  ω    -37.00  85.00   0.50    1.89    --    0.00  57.00   0.00  244
  3  ω    -38.00  39.00   0.50    1.89    --    0.00 -77.00 -60.00  154
  4  ω    -26.00   0.00   0.50    1.89    --    0.00  38.00 -90.00   52
  5  ω    -58.00  33.00   0.50    1.89    --    0.00 -57.00-180.00  182
  6  ω     11.00 135.00   0.50    7.56    --   98.20 -61.00  90.00  248
  7  ω     51.00 134.00   0.50    7.56    --   98.20 -82.00 -60.00  166
  8  ω     44.00 184.00   0.50    7.56    --   98.20  30.00-120.00  280
  9  ω     25.00 140.00   0.50    7.56    --   98.20 -82.00  90.00  230
 10  ω     46.00 115.00   0.50    7.56    --   98.20  30.00-150.00  138
 11  ω     37.00  98.00   0.50    7.56    --   98.20 -82.00-120.00  122
 12  ω     10.00  45.00   0.50    7.56    --   98.20 -82.00 -60.00   70
 13  ω     13.00  89.00   0.50    7.56    --   98.20 -61.00-120.00  152
 14  ω     12.00 186.00   0.50    7.56    --   98.20 -15.00 -90.00  348
 15  ω     50.00 129.00   0.50    7.56    --   98.20 -61.00 -60.00  158
 16  ω     12.00  38.00   0.50    7.56    --   98.20 -82.00 150.00   52
 17  ω     88.00 114.00   0.50    7.56    --   98.20 -82.00  30.00   52
 18  ω     73.00  98.00   0.50    7.56    --   98.20 -82.00-180.00   50
 19  ω     84.00 110.00   0.50    7.56    --   98.20 -82.00 -30.00   52
 20  ω     14.00 123.00   0.50    7.56    --   98.20 -30.00 -90.00  218
;
_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      -0.0341669000
_diffrn_orient_matrix_UB_12      0.0120262000
_diffrn_orient_matrix_UB_13      0.0081233000
_diffrn_orient_matrix_UB_21      -0.0111550000
_diffrn_orient_matrix_UB_22      -0.0365656000
_diffrn_orient_matrix_UB_23      -0.0464268000
_diffrn_orient_matrix_UB_31      -0.0005985000
_diffrn_orient_matrix_UB_32      -0.0043910000
_diffrn_orient_matrix_UB_33      0.4115960000
_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         0.454
_reflns_Friedel_fraction_full    0.648
_reflns_Friedel_fraction_max     0.623
_reflns_number_gt                2566
_reflns_number_total             2696
_reflns_odcompleteness_completeness 99.71
_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 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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         0.215
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.5(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0982P)²+2.7874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1353
_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:
 C004(H004), C00B(H00B), C00C(H00C), C00D(H00D), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.34407(4) 0.60025(4) 0.2917(7) 0.0306(5) Uani 1 1 d . . . . .
N002 N 0.45062(5) 0.43583(6) 0.2996(8) 0.0328(6) Uani 1 1 d . . . . .
N003 N 0.17700(5) 0.68522(5) 0.6501(8) 0.0323(6) Uani 1 1 d . . . . .
C004 C 0.31253(5) 0.49157(6) 0.7094(8) 0.0231(5) Uani 1 1 d . . . . .
H004 H 0.2957 0.4803 0.8109 0.028 Uiso 1 1 calc R . . . .
C005 C 0.33634(5) 0.54222(6) 0.4796(8) 0.0217(5) Uani 1 1 d . . . . .
C006 C 0.28434(5) 0.54939(6) 0.6572(8) 0.0217(5) Uani 1 1 d . . . . .
C007 C 0.24284(5) 0.60367(6) 0.6362(8) 0.0225(5) Uani 1 1 d . . . . .
C008 C 0.29397(5) 0.58095(6) 0.5312(8) 0.0218(5) Uani 1 1 d . . . . .
C009 C 0.31055(5) 0.52542(6) 0.6267(8) 0.0215(5) Uani 1 1 d . . . . .
C00A C 0.39524(5) 0.47217(6) 0.4165(8) 0.0231(6) Uani 1 1 d . . . . .
C00B C 0.27400(5) 0.60820(6) 0.5198(8) 0.0226(5) Uani 1 1 d . . . . .
H00B H 0.2809 0.6290 0.4376 0.027 Uiso 1 1 calc R . . . .
C00C C 0.39473(5) 0.43957(6) 0.2868(9) 0.0263(6) Uani 1 1 d . . . . .
H00C H 0.3758 0.4291 0.2390 0.032 Uiso 1 1 calc R . . . .
C00D C 0.36427(5) 0.52584(6) 0.4127(8) 0.0223(5) Uani 1 1 d . . . . .
H00D H 0.3814 0.5374 0.3209 0.027 Uiso 1 1 calc R . . . .
C00E C 0.22032(5) 0.63184(6) 0.6320(8) 0.0229(6) Uani 1 1 d . . . . .
C00F C 0.36613(5) 0.49128(6) 0.4871(8) 0.0223(5) Uani 1 1 d . . . . .
C00G C 0.32757(5) 0.57812(6) 0.4153(8) 0.0237(6) Uani 1 1 d . . . . .
C00H C 0.42447(5) 0.48656(6) 0.4877(9) 0.0268(6) Uani 1 1 d . . . . .
H00H H 0.4261 0.5085 0.5717 0.032 Uiso 1 1 calc R . . . .
C00I C 0.25393(5) 0.54470(6) 0.7744(8) 0.0229(5) Uani 1 1 d . . . . .
H00I H 0.2473 0.5239 0.8594 0.027 Uiso 1 1 calc R . . . .
C00J C 0.23360(5) 0.57213(6) 0.7608(8) 0.0232(5) Uani 1 1 d . . . . .
H00J H 0.2131 0.5692 0.8378 0.028 Uiso 1 1 calc R . . . .
C00K C 0.34039(5) 0.47488(6) 0.6364(8) 0.0245(6) Uani 1 1 d . . . . .
H00K H 0.3419 0.4521 0.6888 0.029 Uiso 1 1 calc R . . . .
C00L C 0.16856(5) 0.65429(7) 0.5506(9) 0.0300(6) Uani 1 1 d . . . . .
H00L H 0.1479 0.6507 0.4852 0.036 Uiso 1 1 calc R . . . .
C00M C 0.42259(6) 0.42259(7) 0.2283(9) 0.0301(6) Uani 1 1 d . . . . .
H00M H 0.4217 0.4009 0.1348 0.036 Uiso 1 1 calc R . . . .
C00N C 0.18900(5) 0.62721(6) 0.5394(9) 0.0260(6) Uani 1 1 d . . . . .
H00N H 0.1819 0.6061 0.4705 0.031 Uiso 1 1 calc R . . . .
C00O C 0.22931(5) 0.66425(6) 0.7314(9) 0.0261(6) Uani 1 1 d . . . . .
H00O H 0.2499 0.6688 0.7920 0.031 Uiso 1 1 calc R . . . .
C00P C 0.45083(5) 0.46709(7) 0.4292(10) 0.0324(7) Uani 1 1 d . . . . .
H00P H 0.4701 0.4765 0.4845 0.039 Uiso 1 1 calc R . . . .
C00Q C 0.20708(6) 0.68944(7) 0.7383(9) 0.0295(6) Uani 1 1 d . . . . .
H00Q H 0.2134 0.7108 0.8090 0.035 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
O001 C00G 1.219(3) . ?
N002 C00M 1.338(4) . ?
N002 C00P 1.333(4) . ?
N003 C00L 1.335(4) . ?
N003 C00Q 1.341(3) . ?
C004 H004 0.9300 . ?
C004 C009 1.384(3) . ?
C004 C00K 1.393(3) . ?
C005 C009 1.403(3) . ?
C005 C00D 1.385(3) . ?
C005 C00G 1.496(3) . ?
C006 C008 1.402(3) . ?
C006 C009 1.478(3) . ?
C006 C00I 1.386(3) . ?
C007 C00B 1.415(3) . ?
C007 C00E 1.479(3) . ?
C007 C00J 1.395(3) . ?
C008 C00B 1.382(3) . ?
C008 C00G 1.507(3) . ?
C00A C00C 1.384(4) . ?
C00A C00F 1.484(3) . ?
C00A C00H 1.402(3) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00M 1.389(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.404(3) . ?
C00E C00N 1.398(3) . ?
C00E C00O 1.395(3) . ?
C00F C00K 1.397(3) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.387(3) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.397(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00N 1.389(3) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.383(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 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
C00P N002 C00M 116.4(2) . . ?
C00L N003 C00Q 116.3(2) . . ?
C009 C004 H004 120.9 . . ?
C009 C004 C00K 118.2(2) . . ?
C00K C004 H004 120.9 . . ?
C009 C005 C00G 108.60(19) . . ?
C00D C005 C009 121.8(2) . . ?
C00D C005 C00G 129.6(2) . . ?
C008 C006 C009 109.14(19) . . ?
C00I C006 C008 120.1(2) . . ?
C00I C006 C009 130.7(2) . . ?
C00B C007 C00E 121.1(2) . . ?
C00J C007 C00B 118.9(2) . . ?
C00J C007 C00E 120.0(2) . . ?
C006 C008 C00G 108.06(19) . . ?
C00B C008 C006 122.0(2) . . ?
C00B C008 C00G 129.9(2) . . ?
C004 C009 C005 120.1(2) . . ?
C004 C009 C006 131.1(2) . . ?
C005 C009 C006 108.8(2) . . ?
C00C C00A C00F 121.9(2) . . ?
C00C C00A C00H 117.5(2) . . ?
C00H C00A C00F 120.6(2) . . ?
C007 C00B H00B 120.8 . . ?
C008 C00B C007 118.4(2) . . ?
C008 C00B H00B 120.8 . . ?
C00A C00C H00C 120.1 . . ?
C00A C00C C00M 119.8(2) . . ?
C00M C00C H00C 120.1 . . ?
C005 C00D H00D 120.9 . . ?
C005 C00D C00F 118.3(2) . . ?
C00F C00D H00D 120.9 . . ?
C00N C00E C007 122.0(2) . . ?
C00O C00E C007 121.1(2) . . ?
C00O C00E C00N 116.9(2) . . ?
C00D C00F C00A 120.9(2) . . ?
C00K C00F C00A 119.7(2) . . ?
C00K C00F C00D 119.4(2) . . ?
O001 C00G C005 127.2(2) . . ?
O001 C00G C008 127.4(2) . . ?
C005 C00G C008 105.40(19) . . ?
C00A C00H H00H 121.0 . . ?
C00P C00H C00A 118.0(2) . . ?
C00P C00H H00H 121.0 . . ?
C006 C00I H00I 121.0 . . ?
C006 C00I C00J 118.0(2) . . ?
C00J C00I H00I 121.0 . . ?
C007 C00J C00I 122.5(2) . . ?
C007 C00J H00J 118.8 . . ?
C00I C00J H00J 118.8 . . ?
C004 C00K C00F 122.2(2) . . ?
C004 C00K H00K 118.9 . . ?
C00F C00K H00K 118.9 . . ?
N003 C00L H00L 118.2 . . ?
N003 C00L C00N 123.5(2) . . ?
C00N C00L H00L 118.2 . . ?
N002 C00M C00C 123.3(3) . . ?
N002 C00M H00M 118.3 . . ?
C00C C00M H00M 118.3 . . ?
C00E C00N H00N 120.1 . . ?
C00L C00N C00E 119.7(2) . . ?
C00L C00N H00N 120.1 . . ?
C00E C00O H00O 120.5 . . ?
C00Q C00O C00E 118.9(2) . . ?
C00Q C00O H00O 120.5 . . ?
N002 C00P C00H 124.9(2) . . ?
N002 C00P H00P 117.6 . . ?
C00H C00P H00P 117.6 . . ?
N003 C00Q C00O 124.6(2) . . ?
N003 C00Q H00Q 117.7 . . ?
C00O C00Q H00Q 117.7 . . ?

_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.748
