# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_r20210609c
_database_code_depnum_ccdc_archive 'CCDC 2143347'
loop_
_audit_author_name
_audit_author_address
'Yue Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N O2'
_chemical_formula_sum            'C21 H15 N O2'
_chemical_formula_weight         313.34
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   4.6945(2)
_cell_length_b                   9.6477(3)
_cell_length_c                   33.0272(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1495.84(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10059
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.2840
_cell_measurement_theta_min      2.1490
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            16364
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.298
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50    3.00    --  -30.00  45.00   0.00  360
  2  ω   -120.00  30.00   0.50    3.00    --  -30.00  45.00  90.00  300
  3  ω   -120.00  10.00   0.50    3.00    --  -30.00  45.00 180.00  260
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0033620000
_diffrn_orient_matrix_UB_12      0.0726435000
_diffrn_orient_matrix_UB_13      -0.0032821000
_diffrn_orient_matrix_UB_21      -0.0153505000
_diffrn_orient_matrix_UB_22      -0.0113283000
_diffrn_orient_matrix_UB_23      -0.0211070000
_diffrn_orient_matrix_UB_31      -0.1502628000
_diffrn_orient_matrix_UB_32      -0.0004507000
_diffrn_orient_matrix_UB_33      0.0022234000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                4238
_reflns_number_total             4918
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.231
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.2458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C16(H16), C17(H17), C19(H19), C20(H20),
 C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5685(5) 0.93695(17) 0.31492(5) 0.0467(5) Uani 1 1 d . . . . .
O2 O 1.0319(5) 0.5550(2) 0.26869(5) 0.0514(5) Uani 1 1 d . . . . .
N1 N 0.8170(4) 0.73830(17) 0.30060(5) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.6327(5) 0.8464(2) 0.29120(6) 0.0296(4) Uani 1 1 d . . . . .
C2 C 0.5352(5) 0.8288(2) 0.24806(6) 0.0345(5) Uani 1 1 d . . . . .
H2A H 0.572178 0.913993 0.232182 0.041 Uiso 1 1 calc R . . . .
H2B H 0.328999 0.807713 0.246974 0.041 Uiso 1 1 calc R . . . .
C3 C 0.7089(6) 0.7082(2) 0.23181(6) 0.0390(5) Uani 1 1 d . . . . .
H3A H 0.582738 0.635385 0.220677 0.047 Uiso 1 1 calc R . . . .
H3B H 0.840193 0.739680 0.210226 0.047 Uiso 1 1 calc R . . . .
C4 C 0.8730(5) 0.6544(2) 0.26767(6) 0.0332(4) Uani 1 1 d . . . . .
C5 C 0.9497(5) 0.7223(2) 0.34068(6) 0.0299(4) Uani 1 1 d . . . . .
H5A H 1.048461 0.809449 0.347934 0.036 Uiso 1 1 calc R . . . .
H5B H 1.094419 0.647764 0.339337 0.036 Uiso 1 1 calc R . . . .
C6 C 0.7351(4) 0.68740(19) 0.37343(5) 0.0243(4) Uani 1 1 d . . . . .
C7 C 0.6401(5) 0.79428(19) 0.39846(5) 0.0269(4) Uani 1 1 d . . . . .
H7 H 0.712755 0.885209 0.394536 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4433(5) 0.77134(19) 0.42880(5) 0.0269(4) Uani 1 1 d . . . . .
H8 H 0.384277 0.846239 0.445485 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3296(4) 0.63903(18) 0.43527(5) 0.0231(4) Uani 1 1 d . . . . .
C10 C 0.1229(5) 0.6122(2) 0.46642(5) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.060641 0.686179 0.483216 0.033 Uiso 1 1 calc R . . . .
C11 C 0.0166(5) 0.4851(2) 0.47219(5) 0.0297(4) Uani 1 1 d . . . . .
H11 H -0.119144 0.470565 0.493091 0.036 Uiso 1 1 calc R . . . .
C12 C 0.1039(4) 0.36922(19) 0.44730(5) 0.0249(4) Uani 1 1 d . . . . .
C13 C 0.3087(4) 0.39267(17) 0.41632(5) 0.0210(3) Uani 1 1 d . . . . .
C14 C 0.4232(4) 0.52810(17) 0.41009(5) 0.0205(3) Uani 1 1 d . . . . .
C15 C 0.6276(4) 0.55218(18) 0.37894(5) 0.0215(3) Uani 1 1 d . . . . .
C16 C 0.7163(4) 0.4352(2) 0.35457(5) 0.0263(4) Uani 1 1 d . . . . .
H16 H 0.854415 0.448591 0.333915 0.032 Uiso 1 1 calc R . . . .
C17 C 0.6064(5) 0.30707(19) 0.36063(5) 0.0270(4) Uani 1 1 d . . . . .
H17 H 0.669560 0.232699 0.344050 0.032 Uiso 1 1 calc R . . . .
C18 C 0.3977(4) 0.28039(18) 0.39128(5) 0.0243(4) Uani 1 1 d . . . . .
C19 C 0.2799(5) 0.14846(19) 0.39763(6) 0.0312(4) Uani 1 1 d . . . . .
H19 H 0.336119 0.073223 0.380889 0.037 Uiso 1 1 calc R . . . .
C20 C 0.0815(5) 0.1271(2) 0.42824(7) 0.0343(5) Uani 1 1 d . . . . .
H20 H 0.005428 0.037013 0.432442 0.041 Uiso 1 1 calc R . . . .
C21 C -0.0067(5) 0.2356(2) 0.45271(6) 0.0314(4) Uani 1 1 d . . . . .
H21 H -0.143592 0.219271 0.473356 0.038 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.212(3) . ?
O2 C4 1.216(3) . ?
N1 C1 1.390(3) . ?
N1 C4 1.381(3) . ?
N1 C5 1.471(2) . ?
C1 C2 1.506(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.519(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.505(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.516(3) . ?
C6 C7 1.395(3) . ?
C6 C15 1.411(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.400(3) . ?
C9 C10 1.438(3) . ?
C9 C14 1.425(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.338(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.447(3) . ?
C12 C13 1.422(3) . ?
C12 C21 1.401(3) . ?
C13 C14 1.428(2) . ?
C13 C18 1.425(2) . ?
C14 C15 1.426(2) . ?
C15 C16 1.447(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.355(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.432(3) . ?
C18 C19 1.403(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(3) . ?
C21 H21 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 122.92(17) . . ?
C4 N1 C1 112.47(16) . . ?
C4 N1 C5 124.50(17) . . ?
O1 C1 N1 123.45(19) . . ?
O1 C1 C2 128.1(2) . . ?
N1 C1 C2 108.42(18) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.91(17) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.13(17) . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
O2 C4 N1 123.9(2) . . ?
O2 C4 C3 127.4(2) . . ?
N1 C4 C3 108.67(18) . . ?
N1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
N1 C5 C6 112.58(16) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C7 C6 C5 118.12(18) . . ?
C7 C6 C15 119.53(17) . . ?
C15 C6 C5 122.34(17) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.69(17) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.79(16) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 122.03(16) . . ?
C8 C9 C14 118.58(17) . . ?
C14 C9 C10 119.38(17) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.24(17) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.45(18) . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 118.51(16) . . ?
C21 C12 C11 122.23(18) . . ?
C21 C12 C13 119.26(17) . . ?
C12 C13 C14 120.25(15) . . ?
C12 C13 C18 119.64(16) . . ?
C18 C13 C14 120.10(16) . . ?
C9 C14 C13 119.15(16) . . ?
C9 C14 C15 120.41(16) . . ?
C15 C14 C13 120.43(15) . . ?
C6 C15 C14 118.99(15) . . ?
C6 C15 C16 123.12(17) . . ?
C14 C15 C16 117.90(16) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.32(17) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 121.94(16) . . ?
C18 C17 H17 119.0 . . ?
C13 C18 C17 118.30(16) . . ?
C19 C18 C13 119.15(18) . . ?
C19 C18 C17 122.56(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.47(18) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.83(19) . . ?
C21 C20 H20 119.6 . . ?
C12 C21 H21 119.7 . . ?
C20 C21 C12 120.6(2) . . ?
C20 C21 H21 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 173.7(2) . . . . ?
N1 C1 C2 C3 -6.3(2) . . . . ?
N1 C5 C6 C7 -99.8(2) . . . . ?
N1 C5 C6 C15 79.4(2) . . . . ?
C1 N1 C4 O2 178.8(2) . . . . ?
C1 N1 C4 C3 -0.7(2) . . . . ?
C1 N1 C5 C6 67.5(2) . . . . ?
C1 C2 C3 C4 5.7(2) . . . . ?
C2 C3 C4 O2 177.2(2) . . . . ?
C2 C3 C4 N1 -3.3(2) . . . . ?
C4 N1 C1 O1 -175.4(2) . . . . ?
C4 N1 C1 C2 4.5(2) . . . . ?
C4 N1 C5 C6 -116.6(2) . . . . ?
C5 N1 C1 O1 0.8(3) . . . . ?
C5 N1 C1 C2 -179.16(17) . . . . ?
C5 N1 C4 O2 2.6(3) . . . . ?
C5 N1 C4 C3 -176.96(18) . . . . ?
C5 C6 C7 C8 179.50(17) . . . . ?
C5 C6 C15 C14 -179.15(16) . . . . ?
C5 C6 C15 C16 1.3(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C6 C15 C16 C17 -179.51(18) . . . . ?
C7 C6 C15 C14 0.1(3) . . . . ?
C7 C6 C15 C16 -179.46(17) . . . . ?
C7 C8 C9 C10 -179.55(18) . . . . ?
C7 C8 C9 C14 0.5(3) . . . . ?
C8 C9 C10 C11 -179.96(19) . . . . ?
C8 C9 C14 C13 -179.90(16) . . . . ?
C8 C9 C14 C15 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C9 C14 C15 C6 -0.1(2) . . . . ?
C9 C14 C15 C16 179.48(16) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C10 C9 C14 C15 179.86(16) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C10 C11 C12 C21 -179.50(19) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C11 C12 C13 C18 -179.80(17) . . . . ?
C11 C12 C21 C20 179.88(19) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C12 C13 C14 C15 -179.71(16) . . . . ?
C12 C13 C18 C17 -179.37(16) . . . . ?
C12 C13 C18 C19 0.3(3) . . . . ?
C13 C12 C21 C20 0.0(3) . . . . ?
C13 C14 C15 C6 179.59(16) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C13 C18 C19 C20 -0.8(3) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C14 C13 C18 C17 1.1(2) . . . . ?
C14 C13 C18 C19 -179.27(17) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C6 C7 C8 0.2(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 -1.0(3) . . . . ?
C16 C17 C18 C19 179.35(19) . . . . ?
C17 C18 C19 C20 178.88(18) . . . . ?
C18 C13 C14 C9 179.52(16) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C12 -0.5(3) . . . . ?
C21 C12 C13 C14 179.65(17) . . . . ?
C21 C12 C13 C18 0.1(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.899
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_r20210609b
_database_code_depnum_ccdc_archive 'CCDC 2156008'
loop_
_audit_author_name
_audit_author_address
'yue yuezhangchem'
;Tianjin university
China
;
_audit_update_record             
;
2022-03-03 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H19 N O4'
_chemical_formula_sum            'C26 H19 N O4'
_chemical_formula_weight         409.42
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2348(3)
_cell_length_b                   9.0936(4)
_cell_length_c                   12.7865(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.996(3)
_cell_angle_gamma                90
_cell_volume                     953.87(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8583
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.7760
_cell_measurement_theta_min      2.4660
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.483
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0615409000
_diffrn_orient_matrix_UB_12      -0.0094467000
_diffrn_orient_matrix_UB_13      -0.0418279000
_diffrn_orient_matrix_UB_21      -0.0603943000
_diffrn_orient_matrix_UB_22      0.0014190000
_diffrn_orient_matrix_UB_23      0.0362948000
_diffrn_orient_matrix_UB_31      -0.0063049000
_diffrn_orient_matrix_UB_32      0.0774278000
_diffrn_orient_matrix_UB_33      -0.0057572000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3563
_reflns_number_total             3899
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.183
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.060
_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)+(0.0596P)²+0.0615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1A-C1
 1.4 with sigma of 0.001
3. Others
 Sof(H1BC)=Sof(H1BD)=Sof(O1A)=Sof(H1A)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(O1)=Sof(H1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C12(H12), C13(H13), C15(H15), C16(H16), C21(H21), C22(H22),
 C24(H24), C25(H25), C26(H26)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_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
O2 O 0.8679(2) 0.4662(2) 0.35150(13) 0.0211(4) Uani 1 1 d . . . . .
O3 O 0.8458(2) 0.7094(2) 0.60069(15) 0.0284(5) Uani 1 1 d . . . . .
O4 O 0.4828(2) 0.3770(2) 0.44961(15) 0.0308(5) Uani 1 1 d . . . . .
N1 N 0.6588(3) 0.5309(3) 0.54637(17) 0.0210(5) Uani 1 1 d . . . . .
C1 C 1.0728(3) 0.6394(3) 0.4215(2) 0.0272(6) Uani 1 1 d D . . . .
H1AA H 1.085830 0.743764 0.442532 0.033 Uiso 0.827(6) 1 calc R . P A 1
H1AB H 1.076762 0.579583 0.486362 0.033 Uiso 0.827(6) 1 calc R . P A 1
H1BC H 1.077612 0.577999 0.485630 0.033 Uiso 0.173(6) 1 calc R . P A 2
H1BD H 1.157872 0.603514 0.377640 0.033 Uiso 0.173(6) 1 calc R . P A 2
C2 C 0.9083(3) 0.6198(3) 0.3617(2) 0.0201(6) Uani 1 1 d . . . . .
C3 C 0.8828(3) 0.6713(3) 0.2479(2) 0.0233(6) Uani 1 1 d . . . . .
H3 H 0.940444 0.747112 0.215861 0.028 Uiso 1 1 calc R . . . .
C4 C 0.7636(3) 0.5887(3) 0.2029(2) 0.0256(6) Uani 1 1 d . . . . .
H4 H 0.717829 0.593502 0.132139 0.031 Uiso 1 1 calc R . . . .
C5 C 0.7158(3) 0.4847(3) 0.28791(19) 0.0212(5) Uani 1 1 d . . . . .
H5 H 0.661322 0.391594 0.262239 0.025 Uiso 1 1 calc R . . . .
C6 C 0.6197(3) 0.5780(3) 0.3646(2) 0.0207(5) Uani 1 1 d . . . . .
H6 H 0.524707 0.631960 0.328780 0.025 Uiso 1 1 calc R . . . .
C7 C 0.5750(3) 0.4818(3) 0.4542(2) 0.0208(5) Uani 1 1 d . . . . .
C8 C 0.7621(3) 0.6478(3) 0.5310(2) 0.0203(5) Uani 1 1 d . . . . .
C9 C 0.7542(3) 0.6805(3) 0.41431(19) 0.0181(5) Uani 1 1 d . . . . .
H9 H 0.732096 0.786498 0.397996 0.022 Uiso 1 1 calc R . . . .
C10 C 0.6503(3) 0.4586(3) 0.6476(2) 0.0231(6) Uani 1 1 d . . . . .
H10A H 0.745428 0.489481 0.695198 0.028 Uiso 1 1 calc R . . . .
H10B H 0.658132 0.351019 0.637506 0.028 Uiso 1 1 calc R . . . .
C11 C 0.4954(3) 0.4919(3) 0.70017(19) 0.0189(5) Uani 1 1 d . . . . .
C12 C 0.3703(3) 0.5763(3) 0.65088(19) 0.0202(5) Uani 1 1 d . . . . .
H12 H 0.381942 0.615033 0.582925 0.024 Uiso 1 1 calc R . . . .
C13 C 0.2282(3) 0.6054(3) 0.6990(2) 0.0197(5) Uani 1 1 d . . . . .
H13 H 0.144187 0.662533 0.663197 0.024 Uiso 1 1 calc R . . . .
C14 C 0.2080(3) 0.5516(3) 0.79915(19) 0.0190(5) Uani 1 1 d . . . . .
C15 C 0.0639(3) 0.5806(3) 0.8515(2) 0.0236(6) Uani 1 1 d . . . . .
H15 H -0.022898 0.634333 0.815798 0.028 Uiso 1 1 calc R . . . .
C16 C 0.0490(3) 0.5335(3) 0.9497(2) 0.0259(6) Uani 1 1 d . . . . .
H16 H -0.047985 0.555075 0.981931 0.031 Uiso 1 1 calc R . . . .
C17 C 0.1765(3) 0.4512(3) 1.0074(2) 0.0216(6) Uani 1 1 d . . . . .
C18 C 0.3203(3) 0.4167(3) 0.9565(2) 0.0182(5) Uani 1 1 d . . . . .
C19 C 0.3359(3) 0.4665(3) 0.85206(19) 0.0172(5) Uani 1 1 d . . . . .
C20 C 0.4797(3) 0.4346(3) 0.80149(19) 0.0183(5) Uani 1 1 d . . . . .
C21 C 0.6052(3) 0.3480(3) 0.8585(2) 0.0223(6) Uani 1 1 d . . . . .
H21 H 0.700381 0.322810 0.825455 0.027 Uiso 1 1 calc R . . . .
C22 C 0.5902(3) 0.3019(3) 0.9580(2) 0.0242(6) Uani 1 1 d . . . . .
H22 H 0.675762 0.246118 0.993363 0.029 Uiso 1 1 calc R . . . .
C23 C 0.4477(3) 0.3353(3) 1.01136(19) 0.0197(5) Uani 1 1 d . . . . .
C24 C 0.4318(3) 0.2919(3) 1.1149(2) 0.0239(6) Uani 1 1 d . . . . .
H24 H 0.516552 0.236817 1.151794 0.029 Uiso 1 1 calc R . . . .
C25 C 0.2943(3) 0.3281(3) 1.1644(2) 0.0272(6) Uani 1 1 d . . . . .
H25 H 0.286025 0.298486 1.234981 0.033 Uiso 1 1 calc R . . . .
C26 C 0.1685(3) 0.4071(3) 1.1118(2) 0.0272(6) Uani 1 1 d . . . . .
H26 H 0.075388 0.431697 1.147082 0.033 Uiso 1 1 calc R . . . .
O1 O 1.2038(3) 0.5989(3) 0.3641(2) 0.0358(8) Uani 0.827(6) 1 d . . P A 1
H1 H 1.206207 0.506956 0.358080 0.054 Uiso 0.827(6) 1 calc GR . P A 1
O1A O 1.1075(15) 0.7852(5) 0.4503(10) 0.039(4) Uani 0.173(6) 1 d D . P A 2
H1A H 1.057998 0.807016 0.502944 0.058 Uiso 0.173(6) 1 calc GR . 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
O2 C2 1.439(3) . ?
O2 C5 1.443(3) . ?
O3 C8 1.215(3) . ?
O4 C7 1.217(3) . ?
N1 C7 1.386(3) . ?
N1 C8 1.386(3) . ?
N1 C10 1.459(3) . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 C2 1.507(4) . ?
C1 O1 1.406(3) . ?
C1 O1A 1.3989(15) . ?
C2 C3 1.526(4) . ?
C2 C9 1.586(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.327(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.519(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.562(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.513(4) . ?
C6 C9 1.542(3) . ?
C8 C9 1.517(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.523(3) . ?
C11 C12 1.391(4) . ?
C11 C20 1.413(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(3) . ?
C14 C15 1.437(3) . ?
C14 C19 1.428(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.342(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.440(4) . ?
C17 C18 1.434(3) . ?
C17 C26 1.401(3) . ?
C18 C19 1.427(3) . ?
C18 C23 1.418(3) . ?
C19 C20 1.427(3) . ?
C20 C21 1.445(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.355(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.441(4) . ?
C23 C24 1.399(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(4) . ?
C26 H26 0.9500 . ?
O1 H1 0.8400 . ?
O1A H1A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C5 96.9(2) . . ?
C7 N1 C8 113.1(2) . . ?
C7 N1 C10 123.4(2) . . ?
C8 N1 C10 123.3(2) . . ?
H1AA C1 H1AB 107.7 . . ?
H1BC C1 H1BD 107.7 . . ?
C2 C1 H1AA 108.8 . . ?
C2 C1 H1AB 108.8 . . ?
C2 C1 H1BC 108.9 . . ?
C2 C1 H1BD 108.9 . . ?
O1 C1 H1AA 108.8 . . ?
O1 C1 H1AB 108.8 . . ?
O1 C1 C2 113.6(2) . . ?
O1A C1 H1BC 108.9 . . ?
O1A C1 H1BD 108.9 . . ?
O1A C1 C2 113.6(6) . . ?
O2 C2 C1 110.6(2) . . ?
O2 C2 C3 101.5(2) . . ?
O2 C2 C9 100.89(19) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 C9 117.4(2) . . ?
C3 C2 C9 104.4(2) . . ?
C2 C3 H3 127.0 . . ?
C4 C3 C2 106.0(2) . . ?
C4 C3 H3 127.0 . . ?
C3 C4 H4 127.2 . . ?
C3 C4 C5 105.7(2) . . ?
C5 C4 H4 127.2 . . ?
O2 C5 C4 102.1(2) . . ?
O2 C5 H5 115.4 . . ?
O2 C5 C6 99.89(19) . . ?
C4 C5 H5 115.4 . . ?
C4 C5 C6 106.8(2) . . ?
C6 C5 H5 115.4 . . ?
C5 C6 H6 113.5 . . ?
C7 C6 C5 109.4(2) . . ?
C7 C6 H6 113.5 . . ?
C7 C6 C9 104.5(2) . . ?
C9 C6 C5 101.67(19) . . ?
C9 C6 H6 113.5 . . ?
O4 C7 N1 123.8(2) . . ?
O4 C7 C6 127.4(2) . . ?
N1 C7 C6 108.8(2) . . ?
O3 C8 N1 124.4(2) . . ?
O3 C8 C9 127.2(2) . . ?
N1 C8 C9 108.4(2) . . ?
C2 C9 H9 112.7 . . ?
C6 C9 C2 100.79(19) . . ?
C6 C9 H9 112.7 . . ?
C8 C9 C2 112.4(2) . . ?
C8 C9 C6 104.8(2) . . ?
C8 C9 H9 112.7 . . ?
N1 C10 H10A 108.7 . . ?
N1 C10 H10B 108.7 . . ?
N1 C10 C11 114.1(2) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 C20 119.7(2) . . ?
C20 C11 C10 118.6(2) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 122.2(2) . . ?
C13 C14 C19 118.9(2) . . ?
C19 C14 C15 118.9(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 118.4(2) . . ?
C26 C17 C16 123.0(2) . . ?
C26 C17 C18 118.6(2) . . ?
C19 C18 C17 120.0(2) . . ?
C23 C18 C17 119.6(2) . . ?
C23 C18 C19 120.3(2) . . ?
C18 C19 C14 119.5(2) . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 C14 120.1(2) . . ?
C11 C20 C19 119.1(2) . . ?
C11 C20 C21 123.0(2) . . ?
C19 C20 C21 117.9(2) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.5(2) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.6(2) . . ?
C23 C22 H22 119.2 . . ?
C18 C23 C22 118.3(2) . . ?
C24 C23 C18 119.3(2) . . ?
C24 C23 C22 122.4(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.5(2) . . ?
C26 C25 H25 119.7 . . ?
C17 C26 H26 119.5 . . ?
C25 C26 C17 121.1(3) . . ?
C25 C26 H26 119.5 . . ?
C1 O1 H1 109.5 . . ?
C1 O1A H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 31.8(3) . . . . ?
O2 C2 C9 C6 -32.7(2) . . . . ?
O2 C2 C9 C8 78.4(2) . . . . ?
O2 C5 C6 C7 -71.5(2) . . . . ?
O2 C5 C6 C9 38.6(2) . . . . ?
O3 C8 C9 C2 75.6(3) . . . . ?
O3 C8 C9 C6 -175.8(3) . . . . ?
N1 C8 C9 C2 -103.0(2) . . . . ?
N1 C8 C9 C6 5.6(3) . . . . ?
N1 C10 C11 C12 4.0(4) . . . . ?
N1 C10 C11 C20 -176.1(2) . . . . ?
C1 C2 C3 C4 153.6(3) . . . . ?
C1 C2 C9 C6 -152.9(2) . . . . ?
C1 C2 C9 C8 -41.8(3) . . . . ?
C2 O2 C5 C4 49.0(2) . . . . ?
C2 O2 C5 C6 -60.7(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C2 C9 C6 72.3(2) . . . . ?
C3 C2 C9 C8 -176.6(2) . . . . ?
C3 C4 C5 O2 -30.9(3) . . . . ?
C3 C4 C5 C6 73.5(3) . . . . ?
C4 C5 C6 C7 -177.4(2) . . . . ?
C4 C5 C6 C9 -67.4(2) . . . . ?
C5 O2 C2 C1 -176.7(2) . . . . ?
C5 O2 C2 C3 -49.0(2) . . . . ?
C5 O2 C2 C9 58.3(2) . . . . ?
C5 C6 C7 O4 -65.6(3) . . . . ?
C5 C6 C7 N1 113.8(2) . . . . ?
C5 C6 C9 C2 -3.5(2) . . . . ?
C5 C6 C9 C8 -120.4(2) . . . . ?
C7 N1 C8 O3 179.1(2) . . . . ?
C7 N1 C8 C9 -2.3(3) . . . . ?
C7 N1 C10 C11 -77.9(3) . . . . ?
C7 C6 C9 C2 110.3(2) . . . . ?
C7 C6 C9 C8 -6.6(2) . . . . ?
C8 N1 C7 O4 177.2(2) . . . . ?
C8 N1 C7 C6 -2.2(3) . . . . ?
C8 N1 C10 C11 107.8(3) . . . . ?
C9 C2 C3 C4 -72.8(3) . . . . ?
C9 C6 C7 O4 -173.8(3) . . . . ?
C9 C6 C7 N1 5.6(3) . . . . ?
C10 N1 C7 O4 2.4(4) . . . . ?
C10 N1 C7 C6 -177.0(2) . . . . ?
C10 N1 C8 O3 -6.2(4) . . . . ?
C10 N1 C8 C9 172.5(2) . . . . ?
C10 C11 C12 C13 179.4(2) . . . . ?
C10 C11 C20 C19 179.3(2) . . . . ?
C10 C11 C20 C21 1.2(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C11 C20 C21 C22 176.1(3) . . . . ?
C12 C11 C20 C19 -0.9(4) . . . . ?
C12 C11 C20 C21 -179.0(2) . . . . ?
C12 C13 C14 C15 179.4(2) . . . . ?
C12 C13 C14 C19 0.3(4) . . . . ?
C13 C14 C15 C16 -177.0(3) . . . . ?
C13 C14 C19 C18 177.0(2) . . . . ?
C13 C14 C19 C20 -1.6(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C14 C19 C20 C11 1.9(4) . . . . ?
C14 C19 C20 C21 -179.9(2) . . . . ?
C15 C14 C19 C18 -2.1(4) . . . . ?
C15 C14 C19 C20 179.3(2) . . . . ?
C15 C16 C17 C18 -1.5(4) . . . . ?
C15 C16 C17 C26 176.6(3) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C16 C17 C18 C23 -179.8(2) . . . . ?
C16 C17 C26 C25 -179.9(3) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C17 C18 C19 C20 179.0(2) . . . . ?
C17 C18 C23 C22 179.7(2) . . . . ?
C17 C18 C23 C24 -1.0(4) . . . . ?
C18 C17 C26 C25 -1.9(4) . . . . ?
C18 C19 C20 C11 -176.7(2) . . . . ?
C18 C19 C20 C21 1.5(4) . . . . ?
C18 C23 C24 C25 -0.4(4) . . . . ?
C19 C14 C15 C16 2.0(4) . . . . ?
C19 C18 C23 C22 -1.4(4) . . . . ?
C19 C18 C23 C24 177.9(2) . . . . ?
C19 C20 C21 C22 -2.0(4) . . . . ?
C20 C11 C12 C13 -0.4(4) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C21 C22 C23 C18 0.9(4) . . . . ?
C21 C22 C23 C24 -178.3(3) . . . . ?
C22 C23 C24 C25 178.9(3) . . . . ?
C23 C18 C19 C14 -178.4(2) . . . . ?
C23 C18 C19 C20 0.2(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C17 0.5(4) . . . . ?
C26 C17 C18 C19 -176.8(2) . . . . ?
C26 C17 C18 C23 2.1(4) . . . . ?
O1 C1 C2 O2 72.3(3) . . . . ?
O1 C1 C2 C3 -44.8(4) . . . . ?
O1 C1 C2 C9 -172.7(3) . . . . ?
O1A C1 C2 O2 -169.4(6) . . . . ?
O1A C1 C2 C3 73.4(6) . . . . ?
O1A C1 C2 C9 -54.4(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.683
