# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_cxy3081_0m
_database_code_depnum_ccdc_archive 'CCDC 2102242'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-08-09 deposited with the CCDC.	2022-01-12 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 N2 O'
_chemical_formula_sum            'C25 H18 N2 O'
_chemical_formula_weight         362.41
_chemical_absolute_configuration ad
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   12.1052(4)
_cell_length_b                   13.5976(4)
_cell_length_c                   26.9164(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4430.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0459 after correction.
The Ratio of minimum to maximum transmission is 0.8450.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            39688
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.359
_diffrn_reflns_theta_min         3.642
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                7977
_reflns_number_total             8088
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 3457 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_coef       0.0014(3)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         8088
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.081
_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)+(0.0479P)²+0.5633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0835
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C1(H1), C2(H2A), C3(H3), C6(H6), C10(H10), C11(H11), C12(H12),
  C13(H13), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22),
 C26(H26), C27(H27), C28(H28), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36),
  C37(H37), C41(H41), C44(H44), C45(H45), C46(H46), C47(H47)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C49(H49A,H49B,H49C)
;
_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 -0.13890(10) 0.24621(9) 0.45369(5) 0.0305(3) Uani 1 1 d . . . . .
O2 O -0.38607(10) 0.07709(9) 0.49470(5) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.10825(14) 0.42625(11) 0.37201(6) 0.0328(4) Uani 1 1 d . . . . .
N2 N 0.02878(13) 0.30910(11) 0.42952(5) 0.0305(3) Uani 1 1 d . . . . .
H2 H 0.050141 0.330032 0.458930 0.037 Uiso 1 1 calc R U . . .
C50 C 0.04340(13) -0.02152(11) 0.42230(6) 0.0233(3) Uani 1 1 d . . . . .
N4 N -0.12974(11) -0.04364(10) 0.39120(5) 0.0232(3) Uani 1 1 d . . . . .
N5 N -0.21836(11) 0.04879(10) 0.45764(5) 0.0239(3) Uani 1 1 d . . . . .
H5 H -0.202123 0.110418 0.450828 0.029 Uiso 1 1 calc R U . . .
C1 C 0.6330(2) 0.36910(18) 0.40915(9) 0.0485(5) Uani 1 1 d . . . . .
H1 H 0.711064 0.367393 0.412823 0.058 Uiso 1 1 calc R U . . .
C2 C 0.58429(19) 0.43568(19) 0.37691(9) 0.0484(5) Uani 1 1 d . . . . .
H2A H 0.629194 0.480037 0.358582 0.058 Uiso 1 1 calc R U . . .
C3 C 0.47037(18) 0.43806(16) 0.37119(8) 0.0401(5) Uani 1 1 d . . . . .
H3 H 0.437920 0.483393 0.348649 0.048 Uiso 1 1 calc R U . . .
C4 C 0.40321(17) 0.37429(14) 0.39834(7) 0.0352(4) Uani 1 1 d . . . . .
C5 C 0.28224(18) 0.37434(14) 0.39135(7) 0.0350(4) Uani 1 1 d . . . . .
C6 C 0.21565(17) 0.29511(14) 0.39269(7) 0.0361(4) Uani 1 1 d . . . . .
H6 H 0.241036 0.229846 0.398011 0.043 Uiso 1 1 calc R U . . .
C7 C 0.09567(17) 0.32207(13) 0.38475(7) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.02759(19) 0.26537(13) 0.34715(7) 0.0370(4) Uani 1 1 d . . . . .
C9 C -0.07097(18) 0.23525(12) 0.36882(7) 0.0329(4) Uani 1 1 d . . . . .
C10 C -0.1565(2) 0.19170(14) 0.34212(8) 0.0431(5) Uani 1 1 d . . . . .
H10 H -0.223893 0.173164 0.357628 0.052 Uiso 1 1 calc R U . . .
C11 C -0.1387(3) 0.17679(15) 0.29203(9) 0.0568(7) Uani 1 1 d . . . . .
H11 H -0.195642 0.148997 0.272189 0.068 Uiso 1 1 calc R U . . .
C12 C 0.5670(2) 0.30509(17) 0.43595(9) 0.0486(5) Uani 1 1 d . . . . .
H12 H 0.599869 0.259093 0.458023 0.058 Uiso 1 1 calc R U . . .
C13 C 0.4532(2) 0.30786(15) 0.43069(8) 0.0419(5) Uani 1 1 d . . . . .
H13 H 0.408598 0.263867 0.449403 0.050 Uiso 1 1 calc R U . . .
C14 C 0.21355(16) 0.46046(14) 0.38081(7) 0.0316(4) Uani 1 1 d . . . . .
C15 C -0.06792(15) 0.26267(12) 0.42221(7) 0.0277(4) Uani 1 1 d . . . . .
C16 C -0.0390(3) 0.20186(16) 0.27038(8) 0.0612(8) Uani 1 1 d . . . . .
H16 H -0.027690 0.187612 0.236204 0.073 Uiso 1 1 calc R U . . .
C17 C 0.0463(3) 0.24766(15) 0.29722(8) 0.0529(6) Uani 1 1 d . . . . .
H17 H 0.113842 0.265694 0.281757 0.063 Uiso 1 1 calc R U . . .
C18 C 0.03579(17) 0.50387(13) 0.36690(7) 0.0321(4) Uani 1 1 d . . . . .
C19 C -0.07709(17) 0.50657(15) 0.35904(8) 0.0371(4) Uani 1 1 d . . . . .
H19 H -0.119324 0.447893 0.356585 0.045 Uiso 1 1 calc R U . . .
C20 C -0.12630(18) 0.59870(15) 0.35488(8) 0.0393(4) Uani 1 1 d . . . . .
H20 H -0.203793 0.603089 0.349765 0.047 Uiso 1 1 calc R U . . .
C21 C -0.06351(18) 0.68527(14) 0.35811(7) 0.0375(4) Uani 1 1 d . . . . .
H21 H -0.098994 0.747269 0.354957 0.045 Uiso 1 1 calc R U . . .
C22 C 0.04837(18) 0.68144(13) 0.36577(7) 0.0334(4) Uani 1 1 d . . . . .
H22 H 0.090120 0.740484 0.367676 0.040 Uiso 1 1 calc R U . . .
C23 C 0.10092(17) 0.59024(14) 0.37077(6) 0.0316(4) Uani 1 1 d . . . . .
C24 C 0.21392(16) 0.56195(13) 0.38019(7) 0.0323(4) Uani 1 1 d . . . . .
C25 C 0.30571(18) 0.63321(15) 0.38959(8) 0.0396(5) Uani 1 1 d . . . . .
H25A H 0.364158 0.600737 0.408711 0.059 Uiso 1 1 calc R U . . .
H25B H 0.277360 0.689508 0.408409 0.059 Uiso 1 1 calc R U . . .
H25C H 0.335750 0.656063 0.357814 0.059 Uiso 1 1 calc R U . . .
C26 C 0.39405(16) -0.00601(16) 0.43594(9) 0.0423(5) Uani 1 1 d . . . . .
H26 H 0.472099 -0.003078 0.439309 0.051 Uiso 1 1 calc R U . . .
C27 C 0.32727(16) 0.05218(14) 0.46577(8) 0.0372(4) Uani 1 1 d . . . . .
H27 H 0.359636 0.094618 0.489734 0.045 Uiso 1 1 calc R U . . .
C28 C 0.21343(15) 0.04853(13) 0.46067(7) 0.0305(4) Uani 1 1 d . . . . .
H28 H 0.168137 0.088690 0.481141 0.037 Uiso 1 1 calc R U . . .
C29 C 0.16457(14) -0.01393(12) 0.42557(7) 0.0260(4) Uani 1 1 d . . . . .
C30 C -0.02740(13) -0.01968(12) 0.46078(6) 0.0235(3) Uani 1 1 d . . . . .
H30 H -0.005366 -0.010840 0.494360 0.028 Uiso 1 1 calc R U . . .
C31 C -0.14625(13) -0.03330(12) 0.44457(6) 0.0221(3) Uani 1 1 d . . . . .
C32 C -0.20931(14) -0.11977(12) 0.46631(6) 0.0234(3) Uani 1 1 d . . . . .
C33 C -0.18340(15) -0.21882(12) 0.46587(7) 0.0269(4) Uani 1 1 d . . . . .
H33 H -0.115326 -0.241451 0.452542 0.032 Uiso 1 1 calc R U . . .
C34 C -0.26007(17) -0.28425(13) 0.48554(7) 0.0331(4) Uani 1 1 d . . . . .
H34 H -0.243998 -0.352635 0.485789 0.040 Uiso 1 1 calc R U . . .
C35 C -0.36001(16) -0.25110(14) 0.50486(7) 0.0338(4) Uani 1 1 d . . . . .
H35 H -0.411484 -0.297254 0.517740 0.041 Uiso 1 1 calc R U . . .
C36 C 0.23302(15) -0.07200(14) 0.39588(7) 0.0320(4) Uani 1 1 d . . . . .
H36 H 0.201437 -0.114483 0.371730 0.038 Uiso 1 1 calc R U . . .
C37 C 0.34710(16) -0.06806(15) 0.40144(9) 0.0399(5) Uani 1 1 d . . . . .
H37 H 0.392962 -0.108399 0.381315 0.048 Uiso 1 1 calc R U . . .
C38 C -0.02039(13) -0.03611(12) 0.37647(6) 0.0229(3) Uani 1 1 d . . . . .
C39 C -0.31202(13) 0.02181(12) 0.48107(6) 0.0229(3) Uani 1 1 d . . . . .
C40 C -0.30849(14) -0.08706(13) 0.48604(6) 0.0244(3) Uani 1 1 d . . . . .
C41 C -0.38575(15) -0.15096(14) 0.50558(7) 0.0293(4) Uani 1 1 d . . . . .
H41 H -0.453552 -0.127799 0.518965 0.035 Uiso 1 1 calc R U . . .
C42 C -0.19664(14) -0.05442(12) 0.35055(6) 0.0253(3) Uani 1 1 d . . . . .
C43 C -0.12609(15) -0.05344(12) 0.30871(6) 0.0265(4) Uani 1 1 d . . . . .
C44 C -0.17269(18) -0.05943(14) 0.26122(7) 0.0357(4) Uani 1 1 d . . . . .
H44 H -0.127088 -0.057835 0.232505 0.043 Uiso 1 1 calc R U . . .
C45 C -0.28506(19) -0.06764(17) 0.25677(8) 0.0450(5) Uani 1 1 d . . . . .
H45 H -0.317308 -0.071709 0.224656 0.054 Uiso 1 1 calc R U . . .
C46 C -0.35317(18) -0.07011(18) 0.29885(8) 0.0448(5) Uani 1 1 d . . . . .
H46 H -0.430699 -0.076925 0.294610 0.054 Uiso 1 1 calc R U . . .
C47 C -0.31074(16) -0.06294(14) 0.34620(7) 0.0340(4) Uani 1 1 d . . . . .
H47 H -0.357314 -0.063769 0.374609 0.041 Uiso 1 1 calc R U . . .
C48 C -0.01374(14) -0.04141(12) 0.32574(6) 0.0267(4) Uani 1 1 d . . . . .
C49 C 0.08428(16) -0.03446(15) 0.29195(7) 0.0364(4) Uani 1 1 d . . . . .
H49A H 0.143723 0.001472 0.308724 0.055 Uiso 1 1 calc R U . . .
H49B H 0.063352 0.000453 0.261520 0.055 Uiso 1 1 calc R U . . .
H49C H 0.109876 -0.100755 0.283499 0.055 Uiso 1 1 calc R U . . .


_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 C15 1.227(2) . ?
O2 C39 1.226(2) . ?
N1 C7 1.465(2) . ?
N1 C14 1.377(3) . ?
N1 C18 1.379(3) . ?
N2 H2 0.8800 . ?
N2 C7 1.463(2) . ?
N2 C15 1.344(2) . ?
C50 C29 1.473(2) . ?
C50 C30 1.345(2) . ?
C50 C38 1.469(2) . ?
N4 C31 1.457(2) . ?
N4 C38 1.386(2) . ?
N4 C42 1.369(2) . ?
N5 H5 0.8800 . ?
N5 C31 1.460(2) . ?
N5 C39 1.348(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(3) . ?
C1 C12 1.384(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 C5 1.476(3) . ?
C4 C13 1.393(3) . ?
C5 C6 1.346(3) . ?
C5 C14 1.464(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.513(3) . ?
C7 C8 1.516(3) . ?
C8 C9 1.390(3) . ?
C8 C17 1.384(3) . ?
C9 C10 1.393(3) . ?
C9 C15 1.485(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9500 . ?
C11 C16 1.384(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C24 1.380(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.405(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 C23 1.418(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.404(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.371(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.400(3) . ?
C23 C24 1.443(3) . ?
C24 C25 1.496(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26 0.9500 . ?
C26 C27 1.387(3) . ?
C26 C37 1.377(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.401(3) . ?
C29 C36 1.396(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.515(2) . ?
C31 C32 1.519(2) . ?
C32 C33 1.383(2) . ?
C32 C40 1.386(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.390(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.392(3) . ?
C35 H35 0.9500 . ?
C35 C41 1.397(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.390(3) . ?
C37 H37 0.9500 . ?
C38 C48 1.370(2) . ?
C39 C40 1.487(2) . ?
C40 C41 1.381(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.413(2) . ?
C42 C47 1.391(3) . ?
C43 C44 1.400(3) . ?
C43 C48 1.444(2) . ?
C44 H44 0.9500 . ?
C44 C45 1.370(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.401(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.378(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.498(2) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?

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
C14 N1 C7 112.49(16) . . ?
C14 N1 C18 110.32(15) . . ?
C18 N1 C7 134.18(17) . . ?
C7 N2 H2 122.6 . . ?
C15 N2 H2 122.6 . . ?
C15 N2 C7 114.70(15) . . ?
C30 C50 C29 125.98(16) . . ?
C30 C50 C38 108.32(14) . . ?
C38 C50 C29 125.66(15) . . ?
C38 N4 C31 113.95(13) . . ?
C42 N4 C31 135.82(14) . . ?
C42 N4 C38 110.13(14) . . ?
C31 N5 H5 123.0 . . ?
C39 N5 H5 123.0 . . ?
C39 N5 C31 114.04(13) . . ?
C2 C1 H1 120.3 . . ?
C12 C1 H1 120.3 . . ?
C12 C1 C2 119.4(2) . . ?
C1 C2 H2A 119.7 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.72(18) . . ?
C13 C4 C3 118.52(19) . . ?
C13 C4 C5 120.70(18) . . ?
C6 C5 C4 126.17(19) . . ?
C6 C5 C14 107.78(18) . . ?
C14 C5 C4 126.04(17) . . ?
C5 C6 H6 123.9 . . ?
C5 C6 C7 112.15(17) . . ?
C7 C6 H6 123.9 . . ?
N1 C7 C6 99.64(15) . . ?
N1 C7 C8 113.08(16) . . ?
N2 C7 N1 111.53(14) . . ?
N2 C7 C6 112.69(16) . . ?
N2 C7 C8 100.83(15) . . ?
C6 C7 C8 119.53(16) . . ?
C9 C8 C7 109.65(16) . . ?
C17 C8 C7 130.4(2) . . ?
C17 C8 C9 119.8(2) . . ?
C8 C9 C10 123.17(18) . . ?
C8 C9 C15 108.11(16) . . ?
C10 C9 C15 128.64(19) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 C9 116.8(2) . . ?
C11 C10 H10 121.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C16 120.8(2) . . ?
C16 C11 H11 119.6 . . ?
C1 C12 H12 119.9 . . ?
C1 C12 C13 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C4 C13 H13 119.6 . . ?
C12 C13 C4 120.9(2) . . ?
C12 C13 H13 119.6 . . ?
N1 C14 C5 106.79(16) . . ?
N1 C14 C24 109.79(17) . . ?
C24 C14 C5 143.17(19) . . ?
O1 C15 N2 126.44(16) . . ?
O1 C15 C9 127.23(16) . . ?
N2 C15 C9 106.33(16) . . ?
C11 C16 H16 118.9 . . ?
C11 C16 C17 122.3(2) . . ?
C17 C16 H16 118.9 . . ?
C8 C17 C16 117.2(3) . . ?
C8 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
N1 C18 C19 131.59(18) . . ?
N1 C18 C23 105.83(17) . . ?
C19 C18 C23 122.57(18) . . ?
C18 C19 H19 121.3 . . ?
C18 C19 C20 117.33(18) . . ?
C20 C19 H19 121.3 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.82(19) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.79(18) . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C24 108.60(17) . . ?
C22 C23 C18 118.28(18) . . ?
C22 C23 C24 133.11(18) . . ?
C14 C24 C23 105.41(17) . . ?
C14 C24 C25 130.39(19) . . ?
C23 C24 C25 124.13(17) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 H26 120.0 . . ?
C37 C26 H26 120.0 . . ?
C37 C26 C27 119.95(17) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.11(18) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.55(18) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C50 120.19(16) . . ?
C36 C29 C50 121.15(16) . . ?
C36 C29 C28 118.57(16) . . ?
C50 C30 H30 123.8 . . ?
C50 C30 C31 112.41(14) . . ?
C31 C30 H30 123.8 . . ?
N4 C31 N5 113.17(13) . . ?
N4 C31 C30 99.53(12) . . ?
N4 C31 C32 111.96(13) . . ?
N5 C31 C30 113.89(13) . . ?
N5 C31 C32 101.45(12) . . ?
C30 C31 C32 117.44(13) . . ?
C33 C32 C31 129.53(16) . . ?
C33 C32 C40 120.81(16) . . ?
C40 C32 C31 109.54(14) . . ?
C32 C33 H33 121.0 . . ?
C32 C33 C34 117.94(17) . . ?
C34 C33 H33 121.0 . . ?
C33 C34 H34 119.5 . . ?
C33 C34 C35 121.01(17) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 119.5 . . ?
C34 C35 C41 120.99(17) . . ?
C41 C35 H35 119.5 . . ?
C29 C36 H36 119.8 . . ?
C37 C36 C29 120.42(18) . . ?
C37 C36 H36 119.8 . . ?
C26 C37 C36 120.40(19) . . ?
C26 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
N4 C38 C50 105.77(14) . . ?
C48 C38 C50 144.44(16) . . ?
C48 C38 N4 109.73(15) . . ?
O2 C39 N5 126.01(15) . . ?
O2 C39 C40 127.20(16) . . ?
N5 C39 C40 106.78(14) . . ?
C32 C40 C39 108.06(15) . . ?
C41 C40 C32 122.06(16) . . ?
C41 C40 C39 129.88(16) . . ?
C35 C41 H41 121.4 . . ?
C40 C41 C35 117.19(17) . . ?
C40 C41 H41 121.4 . . ?
N4 C42 C43 106.16(15) . . ?
N4 C42 C47 131.56(17) . . ?
C47 C42 C43 122.26(17) . . ?
C42 C43 C48 108.49(15) . . ?
C44 C43 C42 118.92(17) . . ?
C44 C43 C48 132.52(17) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 C43 118.99(18) . . ?
C45 C44 H44 120.5 . . ?
C44 C45 H45 119.5 . . ?
C44 C45 C46 121.02(19) . . ?
C46 C45 H45 119.5 . . ?
C45 C46 H46 119.1 . . ?
C47 C46 C45 121.79(19) . . ?
C47 C46 H46 119.1 . . ?
C42 C47 H47 121.5 . . ?
C46 C47 C42 116.99(19) . . ?
C46 C47 H47 121.5 . . ?
C38 C48 C43 105.48(15) . . ?
C38 C48 C49 130.43(17) . . ?
C43 C48 C49 124.07(16) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 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 C39 C40 C32 -179.26(16) . . . . ?
O2 C39 C40 C41 1.4(3) . . . . ?
N1 C7 C8 C9 -113.14(17) . . . . ?
N1 C7 C8 C17 61.9(3) . . . . ?
N1 C14 C24 C23 0.5(2) . . . . ?
N1 C14 C24 C25 177.34(19) . . . . ?
N1 C18 C19 C20 -179.20(19) . . . . ?
N1 C18 C23 C22 178.60(16) . . . . ?
N1 C18 C23 C24 -2.10(19) . . . . ?
N2 C7 C8 C9 6.04(19) . . . . ?
N2 C7 C8 C17 -178.9(2) . . . . ?
C50 C29 C36 C37 -176.27(18) . . . . ?
C50 C30 C31 N4 0.40(17) . . . . ?
C50 C30 C31 N5 -120.31(15) . . . . ?
C50 C30 C31 C32 121.36(16) . . . . ?
C50 C38 C48 C43 -176.8(2) . . . . ?
C50 C38 C48 C49 1.8(4) . . . . ?
N4 C31 C32 C33 58.7(2) . . . . ?
N4 C31 C32 C40 -117.41(15) . . . . ?
N4 C38 C48 C43 -0.32(19) . . . . ?
N4 C38 C48 C49 178.25(17) . . . . ?
N4 C42 C43 C44 -177.55(15) . . . . ?
N4 C42 C43 C48 -0.12(18) . . . . ?
N4 C42 C47 C46 178.15(19) . . . . ?
N5 C31 C32 C33 179.66(17) . . . . ?
N5 C31 C32 C40 3.55(17) . . . . ?
N5 C39 C40 C32 1.88(19) . . . . ?
N5 C39 C40 C41 -177.43(17) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C1 C12 C13 C4 0.4(4) . . . . ?
C2 C1 C12 C13 -0.2(4) . . . . ?
C2 C3 C4 C5 -178.2(2) . . . . ?
C2 C3 C4 C13 -0.7(3) . . . . ?
C3 C4 C5 C6 143.6(2) . . . . ?
C3 C4 C5 C14 -35.2(3) . . . . ?
C3 C4 C13 C12 0.1(3) . . . . ?
C4 C5 C6 C7 179.18(17) . . . . ?
C4 C5 C14 N1 173.88(17) . . . . ?
C4 C5 C14 C24 -13.1(4) . . . . ?
C5 C4 C13 C12 177.5(2) . . . . ?
C5 C6 C7 N1 7.4(2) . . . . ?
C5 C6 C7 N2 -110.89(18) . . . . ?
C5 C6 C7 C8 131.01(19) . . . . ?
C5 C14 C24 C23 -172.4(2) . . . . ?
C5 C14 C24 C25 4.4(4) . . . . ?
C6 C5 C14 N1 -5.1(2) . . . . ?
C6 C5 C14 C24 167.9(2) . . . . ?
C6 C7 C8 C9 130.08(18) . . . . ?
C6 C7 C8 C17 -54.9(3) . . . . ?
C7 N1 C14 C5 10.4(2) . . . . ?
C7 N1 C14 C24 -165.13(15) . . . . ?
C7 N1 C18 C19 -20.0(3) . . . . ?
C7 N1 C18 C23 160.64(19) . . . . ?
C7 N2 C15 O1 -177.60(16) . . . . ?
C7 N2 C15 C9 2.7(2) . . . . ?
C7 C8 C9 C10 172.20(17) . . . . ?
C7 C8 C9 C15 -4.9(2) . . . . ?
C7 C8 C17 C16 -172.7(2) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C8 C9 C15 O1 -178.20(17) . . . . ?
C8 C9 C15 N2 1.5(2) . . . . ?
C9 C8 C17 C16 1.9(3) . . . . ?
C9 C10 C11 C16 1.8(3) . . . . ?
C10 C9 C15 O1 4.9(3) . . . . ?
C10 C9 C15 N2 -175.36(18) . . . . ?
C10 C11 C16 C17 -3.2(4) . . . . ?
C11 C16 C17 C8 1.3(3) . . . . ?
C12 C1 C2 C3 -0.4(4) . . . . ?
C13 C4 C5 C6 -33.7(3) . . . . ?
C13 C4 C5 C14 147.5(2) . . . . ?
C14 N1 C7 N2 108.38(18) . . . . ?
C14 N1 C7 C6 -10.80(19) . . . . ?
C14 N1 C7 C8 -138.82(17) . . . . ?
C14 N1 C18 C19 -178.2(2) . . . . ?
C14 N1 C18 C23 2.43(19) . . . . ?
C14 C5 C6 C7 -1.8(2) . . . . ?
C15 N2 C7 N1 114.98(18) . . . . ?
C15 N2 C7 C6 -133.92(17) . . . . ?
C15 N2 C7 C8 -5.3(2) . . . . ?
C15 C9 C10 C11 178.01(18) . . . . ?
C17 C8 C9 C10 -3.5(3) . . . . ?
C17 C8 C9 C15 179.44(17) . . . . ?
C18 N1 C7 N2 -49.5(3) . . . . ?
C18 N1 C7 C6 -168.7(2) . . . . ?
C18 N1 C7 C8 63.3(3) . . . . ?
C18 N1 C14 C5 173.70(15) . . . . ?
C18 N1 C14 C24 -1.9(2) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C18 C23 C24 C14 1.0(2) . . . . ?
C18 C23 C24 C25 -176.09(17) . . . . ?
C19 C18 C23 C22 -0.8(3) . . . . ?
C19 C18 C23 C24 178.48(17) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?
C21 C22 C23 C24 -178.11(19) . . . . ?
C22 C23 C24 C14 -179.83(19) . . . . ?
C22 C23 C24 C25 3.1(3) . . . . ?
C23 C18 C19 C20 0.1(3) . . . . ?
C26 C27 C28 C29 0.2(3) . . . . ?
C27 C26 C37 C36 0.7(3) . . . . ?
C27 C28 C29 C50 176.56(17) . . . . ?
C27 C28 C29 C36 -0.1(3) . . . . ?
C28 C29 C36 C37 0.4(3) . . . . ?
C29 C50 C30 C31 -177.70(15) . . . . ?
C29 C50 C38 N4 177.14(15) . . . . ?
C29 C50 C38 C48 -6.3(3) . . . . ?
C29 C36 C37 C26 -0.7(3) . . . . ?
C30 C50 C29 C28 -37.2(2) . . . . ?
C30 C50 C29 C36 139.41(18) . . . . ?
C30 C50 C38 N4 -0.78(17) . . . . ?
C30 C50 C38 C48 175.8(2) . . . . ?
C30 C31 C32 C33 -55.5(2) . . . . ?
C30 C31 C32 C40 128.35(15) . . . . ?
C31 N4 C38 C50 1.10(18) . . . . ?
C31 N4 C38 C48 -176.76(14) . . . . ?
C31 N4 C42 C43 176.01(17) . . . . ?
C31 N4 C42 C47 -2.6(3) . . . . ?
C31 N5 C39 O2 -178.36(15) . . . . ?
C31 N5 C39 C40 0.52(18) . . . . ?
C31 C32 C33 C34 -175.38(16) . . . . ?
C31 C32 C40 C39 -3.43(18) . . . . ?
C31 C32 C40 C41 175.94(15) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C32 C40 C41 C35 0.1(3) . . . . ?
C33 C32 C40 C39 -179.94(15) . . . . ?
C33 C32 C40 C41 -0.6(3) . . . . ?
C33 C34 C35 C41 -0.7(3) . . . . ?
C34 C35 C41 C40 0.5(3) . . . . ?
C37 C26 C27 C28 -0.5(3) . . . . ?
C38 C50 C29 C28 145.22(17) . . . . ?
C38 C50 C29 C36 -38.2(2) . . . . ?
C38 C50 C30 C31 0.22(18) . . . . ?
C38 N4 C31 N5 120.30(15) . . . . ?
C38 N4 C31 C30 -0.93(17) . . . . ?
C38 N4 C31 C32 -125.79(15) . . . . ?
C38 N4 C42 C43 -0.08(18) . . . . ?
C38 N4 C42 C47 -178.66(18) . . . . ?
C39 N5 C31 N4 117.67(15) . . . . ?
C39 N5 C31 C30 -129.59(15) . . . . ?
C39 N5 C31 C32 -2.44(17) . . . . ?
C39 C40 C41 C35 179.35(17) . . . . ?
C40 C32 C33 C34 0.4(3) . . . . ?
C42 N4 C31 N5 -55.7(2) . . . . ?
C42 N4 C31 C30 -176.91(17) . . . . ?
C42 N4 C31 C32 58.2(2) . . . . ?
C42 N4 C38 C50 178.12(13) . . . . ?
C42 N4 C38 C48 0.26(19) . . . . ?
C42 C43 C44 C45 -1.0(3) . . . . ?
C42 C43 C48 C38 0.27(19) . . . . ?
C42 C43 C48 C49 -178.41(16) . . . . ?
C43 C42 C47 C46 -0.2(3) . . . . ?
C43 C44 C45 C46 0.0(3) . . . . ?
C44 C43 C48 C38 177.22(19) . . . . ?
C44 C43 C48 C49 -1.5(3) . . . . ?
C44 C45 C46 C47 1.0(4) . . . . ?
C45 C46 C47 C42 -0.9(3) . . . . ?
C47 C42 C43 C44 1.2(3) . . . . ?
C47 C42 C43 C48 178.63(16) . . . . ?
C48 C43 C44 C45 -177.73(19) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.766 0.750 489.0 44.3 ?
2 0.500 -0.904 0.250 489.0 44.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cxy1744_0m
_database_code_depnum_ccdc_archive 'CCDC 2102244'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-08-09 deposited with the CCDC.	2022-01-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N2 O, C3 H7 N O'
_chemical_formula_sum            'C27 H23 N3 O2'
_chemical_formula_weight         421.48
_chemical_absolute_configuration ad
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.3057(3)
_cell_length_b                   10.9987(4)
_cell_length_c                   20.5401(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2102.29(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.60
_cell_measurement_theta_min      4.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0696 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.9300.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14636
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.591
_diffrn_reflns_theta_min         4.305
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3783
_reflns_number_total             3863
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       0.0069(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   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.063
_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)+(0.0312P)²+0.4376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1), N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C22(H22), C4(H4), C16(H16), C20(H20), C13(H13), C10(H10), C24(H24),
 C9(H9), C15(H15), C23(H23), C21(H21), C14(H14), C8(H8), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.23571(12) -0.16317(11) 0.34611(6) 0.0172(3) Uani 1 1 d . . . . .
N1 N -0.00685(14) -0.08790(13) 0.35952(7) 0.0143(3) Uani 1 1 d . . . . .
H1 H 0.011085 -0.123964 0.396905 0.017 Uiso 1 1 d R U . . .
N2 N 0.46811(15) -0.13215(14) 0.31285(7) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.557253 -0.140641 0.326418 0.022 Uiso 1 1 d R U . . .
C12 C -0.12047(18) -0.02866(15) 0.26715(8) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.01249(18) 0.02768(15) 0.26623(8) 0.0149(3) Uani 1 1 d . . . . .
C6 C 0.26385(18) -0.15178(15) 0.25422(8) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.41014(18) -0.18635(16) 0.25839(8) 0.0165(3) Uani 1 1 d . . . . .
C1 C -0.13229(17) -0.10089(15) 0.32754(8) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.23747(18) -0.07267(15) 0.30891(8) 0.0149(3) Uani 1 1 d . . . . .
C19 C 0.17808(19) 0.29400(16) 0.43911(8) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.18113(19) -0.19610(16) 0.20200(8) 0.0169(3) Uani 1 1 d . . . . .
H7 H 0.082516 -0.175022 0.198039 0.020 Uiso 1 1 calc R U . . .
C18 C 0.15166(17) 0.18833(16) 0.39963(8) 0.0170(4) Uani 1 1 d . . . . .
C17 C 0.12825(17) 0.09977(16) 0.36722(8) 0.0163(3) Uani 1 1 d . . . . .
C22 C 0.2305(2) 0.49937(16) 0.51545(8) 0.0206(4) Uani 1 1 d . . . . .
H22 H 0.248355 0.569453 0.541249 0.025 Uiso 1 1 calc R U . . .
C4 C 0.36436(18) -0.06353(16) 0.34220(8) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.378327 -0.016150 0.380347 0.021 Uiso 1 1 calc R U . . .
C16 C 0.05347(18) 0.10087(16) 0.21469(8) 0.0177(4) Uani 1 1 d . . . . .
H16 H 0.143335 0.141852 0.214771 0.021 Uiso 1 1 calc R U . . .
C20 C 0.31754(19) 0.32097(16) 0.45989(8) 0.0184(4) Uani 1 1 d . . . . .
H20 H 0.395152 0.269624 0.447782 0.022 Uiso 1 1 calc R U . . .
C13 C -0.21725(18) -0.01582(17) 0.21612(8) 0.0185(4) Uani 1 1 d . . . . .
H13 H -0.308870 -0.053867 0.217214 0.022 Uiso 1 1 calc R U . . .
C10 C 0.47561(18) -0.26211(16) 0.21252(8) 0.0191(4) Uani 1 1 d . . . . .
H10 H 0.573932 -0.284367 0.216134 0.023 Uiso 1 1 calc R U . . .
C24 C 0.06508(18) 0.37102(16) 0.45693(8) 0.0179(4) Uani 1 1 d . . . . .
H24 H -0.030109 0.353449 0.443119 0.021 Uiso 1 1 calc R U . . .
C9 C 0.39158(19) -0.30323(16) 0.16178(8) 0.0197(4) Uani 1 1 d . . . . .
H9 H 0.432940 -0.354549 0.129643 0.024 Uiso 1 1 calc R U . . .
C15 C -0.04134(19) 0.11236(16) 0.16280(8) 0.0200(4) Uani 1 1 d . . . . .
H15 H -0.014824 0.160235 0.126231 0.024 Uiso 1 1 calc R U . . .
C2 C 0.09857(17) -0.00791(15) 0.32638(8) 0.0148(3) Uani 1 1 d . . . . .
C23 C 0.09186(19) 0.47287(17) 0.49471(8) 0.0195(4) Uani 1 1 d . . . . .
H23 H 0.014799 0.525032 0.506539 0.023 Uiso 1 1 calc R U . . .
C21 C 0.34270(19) 0.42286(17) 0.49825(8) 0.0198(4) Uani 1 1 d . . . . .
H21 H 0.437415 0.440204 0.512790 0.024 Uiso 1 1 calc R U . . .
C14 C -0.1750(2) 0.05465(17) 0.16355(8) 0.0216(4) Uani 1 1 d . . . . .
H14 H -0.237951 0.063837 0.127474 0.026 Uiso 1 1 calc R U . . .
C8 C 0.2459(2) -0.27067(16) 0.15669(8) 0.0190(4) Uani 1 1 d . . . . .
H8 H 0.190770 -0.300742 0.121239 0.023 Uiso 1 1 calc R U . . .
O2 O 0.47248(18) 0.21818(13) -0.01889(6) 0.0339(4) Uani 1 1 d . . . . .
N3 N 0.40342(16) 0.10724(15) 0.06922(8) 0.0230(3) Uani 1 1 d . . . . .
C25 C 0.4882(2) 0.18413(17) 0.03780(9) 0.0238(4) Uani 1 1 d . . . . .
H25 H 0.568173 0.215797 0.061023 0.029 Uiso 1 1 calc R U . . .
C26 C 0.4336(2) 0.0669(2) 0.13510(9) 0.0276(4) Uani 1 1 d . . . . .
H26A H 0.453142 -0.020691 0.134942 0.041 Uiso 1 1 calc R U . . .
H26B H 0.350446 0.083648 0.162944 0.041 Uiso 1 1 calc R U . . .
H26C H 0.517721 0.110392 0.151896 0.041 Uiso 1 1 calc R U . . .
C27 C 0.2763(2) 0.0576(3) 0.03790(12) 0.0456(6) Uani 1 1 d . . . . .
H27A H 0.265022 0.094342 -0.005275 0.068 Uiso 1 1 calc R U . . .
H27B H 0.191467 0.075740 0.064444 0.068 Uiso 1 1 calc R U . . .
H27C H 0.286727 -0.030627 0.033400 0.068 Uiso 1 1 calc R U . . .


_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 1.241(2) . ?
N1 H1 0.8803 . ?
N1 C1 1.347(2) . ?
N1 C2 1.483(2) . ?
N2 H2 0.8801 . ?
N2 C5 1.378(2) . ?
N2 C4 1.366(2) . ?
C12 C11 1.384(2) . ?
C12 C1 1.477(2) . ?
C12 C13 1.389(2) . ?
C11 C16 1.384(2) . ?
C11 C2 1.524(2) . ?
C6 C5 1.416(2) . ?
C6 C3 1.442(2) . ?
C6 C7 1.407(2) . ?
C5 C10 1.398(2) . ?
C3 C4 1.368(2) . ?
C3 C2 1.519(2) . ?
C19 C18 1.438(2) . ?
C19 C20 1.398(2) . ?
C19 C24 1.399(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(2) . ?
C18 C17 1.200(3) . ?
C17 C2 1.477(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(3) . ?
C22 C21 1.386(3) . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.389(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.379(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.385(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.406(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.396(3) . ?
C23 H23 0.9500 . ?
C21 H21 0.9500 . ?
C14 H14 0.9500 . ?
C8 H8 0.9500 . ?
O2 C25 1.232(2) . ?
N3 C25 1.324(3) . ?
N3 C26 1.452(2) . ?
N3 C27 1.453(3) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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 H1 122.8 . . ?
C1 N1 C2 114.35(13) . . ?
C2 N1 H1 122.8 . . ?
C5 N2 H2 125.5 . . ?
C4 N2 H2 125.8 . . ?
C4 N2 C5 108.71(14) . . ?
C11 C12 C1 108.59(14) . . ?
C11 C12 C13 121.59(16) . . ?
C13 C12 C1 129.79(16) . . ?
C12 C11 C2 110.11(14) . . ?
C16 C11 C12 121.16(15) . . ?
C16 C11 C2 128.69(16) . . ?
C5 C6 C3 106.17(15) . . ?
C7 C6 C5 118.62(16) . . ?
C7 C6 C3 135.20(16) . . ?
N2 C5 C6 108.03(15) . . ?
N2 C5 C10 129.40(16) . . ?
C10 C5 C6 122.57(16) . . ?
O1 C1 N1 125.49(16) . . ?
O1 C1 C12 127.77(15) . . ?
N1 C1 C12 106.73(14) . . ?
C6 C3 C2 127.73(15) . . ?
C4 C3 C6 106.66(15) . . ?
C4 C3 C2 125.59(15) . . ?
C20 C19 C18 120.15(16) . . ?
C20 C19 C24 119.30(15) . . ?
C24 C19 C18 120.55(16) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.78(16) . . ?
C8 C7 H7 120.6 . . ?
C17 C18 C19 179.18(19) . . ?
C18 C17 C2 179.00(19) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.57(16) . . ?
N2 C4 C3 110.42(15) . . ?
N2 C4 H4 124.8 . . ?
C3 C4 H4 124.8 . . ?
C11 C16 H16 121.1 . . ?
C11 C16 C15 117.70(16) . . ?
C15 C16 H16 121.1 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.04(16) . . ?
C21 C20 H20 120.0 . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.44(16) . . ?
C14 C13 H13 121.3 . . ?
C5 C10 H10 121.4 . . ?
C9 C10 C5 117.24(16) . . ?
C9 C10 H10 121.4 . . ?
C19 C24 H24 120.0 . . ?
C23 C24 C19 120.06(16) . . ?
C23 C24 H24 120.0 . . ?
C10 C9 H9 119.4 . . ?
C10 C9 C8 121.29(16) . . ?
C8 C9 H9 119.4 . . ?
C16 C15 H15 119.5 . . ?
C16 C15 C14 121.06(16) . . ?
C14 C15 H15 119.5 . . ?
N1 C2 C11 100.18(13) . . ?
N1 C2 C3 113.16(13) . . ?
C3 C2 C11 112.10(13) . . ?
C17 C2 N1 109.79(13) . . ?
C17 C2 C11 110.66(14) . . ?
C17 C2 C3 110.55(14) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.55(17) . . ?
C24 C23 H23 119.7 . . ?
C22 C21 C20 120.47(16) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C13 C14 C15 121.02(16) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C7 C8 C9 121.49(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C25 N3 C26 122.28(16) . . ?
C25 N3 C27 120.61(17) . . ?
C26 N3 C27 117.10(18) . . ?
O2 C25 N3 125.72(19) . . ?
O2 C25 H25 117.1 . . ?
N3 C25 H25 117.1 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
N2 C5 C10 C9 -179.40(17) . . . . ?
C12 C11 C16 C15 -2.3(2) . . . . ?
C12 C11 C2 N1 -1.06(17) . . . . ?
C12 C11 C2 C3 119.22(15) . . . . ?
C12 C11 C2 C17 -116.87(15) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C11 C12 C1 O1 179.26(16) . . . . ?
C11 C12 C1 N1 -1.37(18) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C11 C16 C15 C14 1.7(2) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C6 C3 C4 N2 -0.66(19) . . . . ?
C6 C3 C2 N1 79.8(2) . . . . ?
C6 C3 C2 C11 -32.6(2) . . . . ?
C6 C3 C2 C17 -156.56(16) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C5 N2 C4 C3 1.0(2) . . . . ?
C5 C6 C3 C4 0.04(19) . . . . ?
C5 C6 C3 C2 178.44(15) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C5 C10 C9 C8 -0.3(3) . . . . ?
C1 N1 C2 C11 0.18(17) . . . . ?
C1 N1 C2 C3 -119.34(15) . . . . ?
C1 N1 C2 C17 116.64(15) . . . . ?
C1 C12 C11 C16 179.45(15) . . . . ?
C1 C12 C11 C2 1.52(18) . . . . ?
C1 C12 C13 C14 -177.26(16) . . . . ?
C3 C6 C5 N2 0.58(18) . . . . ?
C3 C6 C5 C10 -178.96(15) . . . . ?
C3 C6 C7 C8 178.61(18) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C19 C24 C23 C22 -0.2(3) . . . . ?
C7 C6 C5 N2 179.90(15) . . . . ?
C7 C6 C5 C10 0.4(2) . . . . ?
C7 C6 C3 C4 -179.11(19) . . . . ?
C7 C6 C3 C2 -0.7(3) . . . . ?
C18 C19 C20 C21 -179.74(16) . . . . ?
C18 C19 C24 C23 -179.69(16) . . . . ?
C4 N2 C5 C6 -0.99(19) . . . . ?
C4 N2 C5 C10 178.50(17) . . . . ?
C4 C3 C2 N1 -102.06(19) . . . . ?
C4 C3 C2 C11 145.53(16) . . . . ?
C4 C3 C2 C17 21.6(2) . . . . ?
C16 C11 C2 N1 -178.78(16) . . . . ?
C16 C11 C2 C3 -58.5(2) . . . . ?
C16 C11 C2 C17 65.4(2) . . . . ?
C16 C15 C14 C13 0.0(3) . . . . ?
C20 C19 C24 C23 0.1(2) . . . . ?
C13 C12 C11 C16 1.0(2) . . . . ?
C13 C12 C11 C2 -176.89(15) . . . . ?
C13 C12 C1 O1 -2.5(3) . . . . ?
C13 C12 C1 N1 176.87(17) . . . . ?
C10 C9 C8 C7 0.2(3) . . . . ?
C24 C19 C20 C21 0.5(2) . . . . ?
C2 N1 C1 O1 -179.92(15) . . . . ?
C2 N1 C1 C12 0.69(18) . . . . ?
C2 C11 C16 C15 175.24(16) . . . . ?
C2 C3 C4 N2 -179.11(15) . . . . ?
C23 C22 C21 C20 0.8(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C26 N3 C25 O2 176.77(18) . . . . ?
C27 N3 C25 O2 -1.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
