# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mo_201124_sja20201118_0m
_database_code_depnum_ccdc_archive 'CCDC 2046044'
loop_
_audit_author_name
_audit_author_address
'Jiankang Zhang'
;Zhejiang University City College
China
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2022-08-11 downloaded from the CCDC.
;
_audit_creation_date             2020-11-24
_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         'C33 H22 N4 O'
_chemical_formula_sum            'C33 H22 N4 O'
_chemical_formula_weight         490.54
_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      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                   13.710(7)
_cell_length_b                   13.465(6)
_cell_length_c                   14.052(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.078(12)
_cell_angle_gamma                90
_cell_volume                     2516.2(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9734
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0793 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.9096.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31446
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.149
_diffrn_reflns_theta_min         2.126
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4388
_reflns_number_total             5544
_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 V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.046
_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)+(0.0484P)²+0.9497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32)
;
_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 0.50824(10) 0.00321(8) 0.33821(9) 0.0489(3) Uani 1 1 d . . . . .
N1 N 0.68550(9) 0.05874(9) 0.48210(9) 0.0321(3) Uani 1 1 d . . . . .
N2 N 0.73158(9) 0.21374(9) 0.69652(9) 0.0319(3) Uani 1 1 d . . . . .
N3 N 0.81248(10) 0.32915(10) 0.62274(10) 0.0399(3) Uani 1 1 d . . . . .
N4 N 1.03941(14) 0.21581(16) 0.6179(2) 0.1004(9) Uani 1 1 d . . . . .
C1 C 0.71956(13) -0.01278(11) 0.42787(12) 0.0390(4) Uani 1 1 d . . . . .
H1 H 0.677281 -0.035552 0.367901 0.047 Uiso 1 1 calc R . . . .
C2 C 0.81307(14) -0.05048(12) 0.46001(14) 0.0453(4) Uani 1 1 d . . . . .
H2 H 0.836072 -0.099873 0.422383 0.054 Uiso 1 1 calc R . . . .
C3 C 0.87703(14) -0.01745(13) 0.54873(14) 0.0452(4) Uani 1 1 d . . . . .
H3 H 0.942352 -0.045110 0.571008 0.054 Uiso 1 1 calc R . . . .
C4 C 0.84492(12) 0.05418(12) 0.60238(12) 0.0372(4) Uani 1 1 d . . . . .
H4 H 0.887707 0.077177 0.661982 0.045 Uiso 1 1 calc R . . . .
C5 C 0.74776(11) 0.09370(11) 0.56858(10) 0.0314(3) Uani 1 1 d . . . . .
C6 C 0.59493(11) 0.11087(11) 0.46208(11) 0.0314(3) Uani 1 1 d . . . . .
C7 C 0.60055(11) 0.17988(11) 0.53939(10) 0.0309(3) Uani 1 1 d . . . . .
C8 C 0.69420(11) 0.16768(11) 0.60326(10) 0.0308(3) Uani 1 1 d . . . . .
C9 C 0.51272(12) 0.08487(11) 0.37854(11) 0.0354(3) Uani 1 1 d . . . . .
C10 C 0.43190(11) 0.15908(11) 0.34243(10) 0.0331(3) Uani 1 1 d . . . . .
C11 C 0.45386(12) 0.25806(11) 0.32944(11) 0.0362(3) Uani 1 1 d . . . . .
H11 H 0.521730 0.280051 0.344568 0.043 Uiso 1 1 calc R . . . .
C12 C 0.37674(14) 0.32441(12) 0.29447(12) 0.0430(4) Uani 1 1 d . . . . .
H12 H 0.391771 0.391813 0.284010 0.052 Uiso 1 1 calc R . . . .
C13 C 0.27791(14) 0.29336(14) 0.27463(13) 0.0471(4) Uani 1 1 d . . . . .
H13 H 0.225066 0.339544 0.251559 0.056 Uiso 1 1 calc R . . . .
C14 C 0.25580(13) 0.19462(14) 0.28841(13) 0.0466(4) Uani 1 1 d . . . . .
H14 H 0.187786 0.173356 0.275805 0.056 Uiso 1 1 calc R . . . .
C15 C 0.33254(12) 0.12749(12) 0.32036(12) 0.0394(4) Uani 1 1 d . . . . .
H15 H 0.317466 0.059413 0.327324 0.047 Uiso 1 1 calc R . . . .
C16 C 0.52375(12) 0.25073(11) 0.55580(10) 0.0330(3) Uani 1 1 d . . . . .
C17 C 0.42561(12) 0.22121(12) 0.55178(11) 0.0372(4) Uani 1 1 d . . . . .
H17 H 0.407263 0.153437 0.540256 0.045 Uiso 1 1 calc R . . . .
C18 C 0.35462(13) 0.28936(14) 0.56437(13) 0.0452(4) Uani 1 1 d . . . . .
H18 H 0.287463 0.268584 0.560050 0.054 Uiso 1 1 calc R . . . .
C19 C 0.38089(15) 0.38747(14) 0.58319(13) 0.0499(4) Uani 1 1 d . . . . .
H19 H 0.331936 0.434251 0.591939 0.060 Uiso 1 1 calc R . . . .
C20 C 0.47800(15) 0.41758(13) 0.58928(14) 0.0499(5) Uani 1 1 d . . . . .
H20 H 0.496140 0.485095 0.603087 0.060 Uiso 1 1 calc R . . . .
C21 C 0.54971(13) 0.35009(12) 0.57541(12) 0.0402(4) Uani 1 1 d . . . . .
H21 H 0.616568 0.371559 0.579271 0.048 Uiso 1 1 calc R . . . .
C22 C 0.70680(12) 0.17143(13) 0.77671(11) 0.0382(4) Uani 1 1 d . . . . .
H22 H 0.660360 0.117848 0.767194 0.046 Uiso 1 1 calc R . . . .
C23 C 0.74702(13) 0.20443(14) 0.86840(12) 0.0455(4) Uani 1 1 d . . . . .
H23 H 0.729483 0.174941 0.923370 0.055 Uiso 1 1 calc R . . . .
C24 C 0.81585(13) 0.28391(14) 0.88046(12) 0.0474(5) Uani 1 1 d . . . . .
H24 H 0.846334 0.307097 0.944660 0.057 Uiso 1 1 calc R . . . .
C25 C 0.83923(12) 0.32766(13) 0.80249(12) 0.0413(4) Uani 1 1 d . . . . .
H25 H 0.885055 0.381790 0.813150 0.050 Uiso 1 1 calc R . . . .
C26 C 0.79672(11) 0.29467(11) 0.70354(11) 0.0334(3) Uani 1 1 d . . . . .
C27 C 0.87738(12) 0.40997(12) 0.62651(12) 0.0396(4) Uani 1 1 d . . . . .
C28 C 0.97781(12) 0.39517(13) 0.62484(12) 0.0420(4) Uani 1 1 d . . . . .
C29 C 1.04258(14) 0.47511(15) 0.62499(14) 0.0513(5) Uani 1 1 d . . . . .
H29 H 1.110936 0.463437 0.625079 0.062 Uiso 1 1 calc R . . . .
C30 C 1.00781(16) 0.57004(15) 0.62503(14) 0.0547(5) Uani 1 1 d . . . . .
H30 H 1.052135 0.624581 0.626645 0.066 Uiso 1 1 calc R . . . .
C31 C 0.90855(17) 0.58626(15) 0.62271(18) 0.0655(6) Uani 1 1 d . . . . .
H31 H 0.884178 0.652453 0.620925 0.079 Uiso 1 1 calc R . . . .
C32 C 0.84311(16) 0.50789(14) 0.62293(17) 0.0594(5) Uani 1 1 d . . . . .
H32 H 0.774459 0.520861 0.620639 0.071 Uiso 1 1 calc R . . . .
C33 C 1.01180(14) 0.29547(16) 0.62121(18) 0.0622(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2318(19) . ?
N1 C1 1.378(2) . ?
N1 C5 1.3865(19) . ?
N1 C6 1.394(2) . ?
N2 C8 1.4275(19) . ?
N2 C22 1.377(2) . ?
N2 C26 1.397(2) . ?
N3 C26 1.293(2) . ?
N3 C27 1.398(2) . ?
N4 C33 1.142(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.350(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.410(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.361(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.405(2) . ?
C5 C8 1.394(2) . ?
C6 C7 1.417(2) . ?
C6 C9 1.459(2) . ?
C7 C8 1.386(2) . ?
C7 C16 1.480(2) . ?
C9 C10 1.487(2) . ?
C10 C11 1.388(2) . ?
C10 C15 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 C21 1.395(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.348(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.409(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.350(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.441(2) . ?
C27 C28 1.397(2) . ?
C27 C32 1.397(3) . ?
C28 C29 1.395(2) . ?
C28 C33 1.426(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.364(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.371(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(3) . ?
C32 H32 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 120.18(13) . . ?
C1 N1 C6 130.18(13) . . ?
C5 N1 C6 109.52(12) . . ?
C22 N2 C8 117.81(13) . . ?
C22 N2 C26 123.06(13) . . ?
C26 N2 C8 118.97(12) . . ?
C26 N3 C27 119.14(13) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 N1 119.97(15) . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.84(16) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.84(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.25(15) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 119.89(14) . . ?
N1 C5 C8 106.54(13) . . ?
C8 C5 C4 133.56(14) . . ?
N1 C6 C7 107.20(12) . . ?
N1 C6 C9 121.17(13) . . ?
C7 C6 C9 131.41(14) . . ?
C6 C7 C16 129.34(13) . . ?
C8 C7 C6 106.72(13) . . ?
C8 C7 C16 123.90(13) . . ?
C5 C8 N2 121.96(13) . . ?
C7 C8 N2 127.75(14) . . ?
C7 C8 C5 110.01(13) . . ?
O1 C9 C6 121.79(15) . . ?
O1 C9 C10 119.56(14) . . ?
C6 C9 C10 118.64(13) . . ?
C11 C10 C9 121.52(14) . . ?
C11 C10 C15 119.82(15) . . ?
C15 C10 C9 118.66(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.77(15) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.35(16) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.94(16) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.93(17) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.14(16) . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C7 121.83(14) . . ?
C17 C16 C21 118.69(15) . . ?
C21 C16 C7 119.48(14) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.68(16) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.17(17) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.92(17) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.47(17) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.05(17) . . ?
C20 C21 H21 120.0 . . ?
N2 C22 H22 119.3 . . ?
C23 C22 N2 121.40(17) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.9 . . ?
C22 C23 C24 118.14(16) . . ?
C24 C23 H23 120.9 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.21(15) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.0 . . ?
C24 C25 C26 121.91(17) . . ?
C26 C25 H25 119.0 . . ?
N2 C26 C25 114.22(14) . . ?
N3 C26 N2 117.30(13) . . ?
N3 C26 C25 128.47(16) . . ?
C28 C27 N3 120.59(15) . . ?
C32 C27 N3 121.86(16) . . ?
C32 C27 C28 117.28(16) . . ?
C27 C28 C33 117.83(16) . . ?
C29 C28 C27 121.30(17) . . ?
C29 C28 C33 120.86(17) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.04(18) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.62(18) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 119.4 . . ?
C30 C31 C32 121.2(2) . . ?
C32 C31 H31 119.4 . . ?
C27 C32 H32 119.8 . . ?
C31 C32 C27 120.45(19) . . ?
C31 C32 H32 119.8 . . ?
N4 C33 C28 179.6(3) . . ?

_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_mo_201019_sja20201012_0m
_database_code_depnum_ccdc_archive 'CCDC 2163189'
loop_
_audit_author_name
_audit_author_address
'Jiankang Zhang'
;Zhejiang University City College
China
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-08-11 downloaded from the CCDC.
;
_audit_creation_date             2020-10-19
_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 H18 N2 O2'
_chemical_formula_sum            'C26 H18 N2 O2'
_chemical_formula_weight         390.42
_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      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                   7.027(2)
_cell_length_b                   17.982(5)
_cell_length_c                   15.561(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.167(11)
_cell_angle_gamma                90
_cell_volume                     1929.1(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7589
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1290 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.9093.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20840
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.118
_diffrn_reflns_theta_min         2.265
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3423
_reflns_number_total             4252
_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 V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.029
_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)+(0.0404P)²+0.5461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_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 0.51577(14) 0.84458(5) 0.52248(7) 0.0378(2) Uani 1 1 d . . . . .
O2 O 0.80597(15) 0.48425(5) 0.51940(6) 0.0392(2) Uani 1 1 d . . . . .
N1 N 0.65711(15) 0.62714(6) 0.45541(7) 0.0266(2) Uani 1 1 d . . . . .
N2 N 0.30694(15) 0.74786(6) 0.52673(7) 0.0260(2) Uani 1 1 d . . . . .
C1 C 0.49676(19) 0.72322(7) 0.35831(8) 0.0299(3) Uani 1 1 d . . . . .
H1 H 0.407918 0.763484 0.346964 0.036 Uiso 1 1 calc R . . . .
C2 C 0.5955(2) 0.70028(8) 0.29591(9) 0.0347(3) Uani 1 1 d . . . . .
H2 H 0.573151 0.723556 0.240049 0.042 Uiso 1 1 calc R . . . .
C3 C 0.7315(2) 0.64156(8) 0.31466(9) 0.0355(3) Uani 1 1 d . . . . .
H3 H 0.802265 0.626668 0.271365 0.043 Uiso 1 1 calc R . . . .
C4 C 0.7630(2) 0.60616(7) 0.39306(9) 0.0309(3) Uani 1 1 d . . . . .
H4 H 0.856409 0.567470 0.405050 0.037 Uiso 1 1 calc R . . . .
C5 C 0.52787(18) 0.68654(7) 0.44000(8) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.45428(18) 0.69596(7) 0.51615(8) 0.0258(3) Uani 1 1 d . . . . .
C7 C 0.53772(18) 0.64375(7) 0.57849(8) 0.0267(3) Uani 1 1 d . . . . .
C8 C 0.66551(18) 0.60005(7) 0.54063(8) 0.0274(3) Uani 1 1 d . . . . .
C9 C 0.35440(19) 0.82401(7) 0.53238(8) 0.0288(3) Uani 1 1 d . . . . .
C10 C 0.2013(2) 0.87137(8) 0.55044(9) 0.0362(3) Uani 1 1 d . . . . .
H10 H 0.223639 0.923397 0.556198 0.043 Uiso 1 1 calc R . . . .
C11 C 0.0271(2) 0.84403(9) 0.55943(9) 0.0378(3) Uani 1 1 d . . . . .
H11 H -0.069979 0.877111 0.571303 0.045 Uiso 1 1 calc R . . . .
C12 C -0.0130(2) 0.76704(9) 0.55148(9) 0.0363(3) Uani 1 1 d . . . . .
H12 H -0.136288 0.748164 0.557042 0.044 Uiso 1 1 calc R . . . .
C13 C 0.12792(19) 0.72101(8) 0.53580(8) 0.0319(3) Uani 1 1 d . . . . .
H13 H 0.103465 0.669071 0.530901 0.038 Uiso 1 1 calc R . . . .
C14 C 0.48627(18) 0.63567(7) 0.66593(8) 0.0277(3) Uani 1 1 d . . . . .
C15 C 0.5146(2) 0.69457(8) 0.72534(9) 0.0345(3) Uani 1 1 d . . . . .
H15 H 0.563042 0.740727 0.709044 0.041 Uiso 1 1 calc R . . . .
C16 C 0.4722(2) 0.68584(9) 0.80837(9) 0.0420(4) Uani 1 1 d . . . . .
H16 H 0.493374 0.725815 0.849026 0.050 Uiso 1 1 calc R . . . .
C17 C 0.3993(2) 0.61923(10) 0.83182(10) 0.0454(4) Uani 1 1 d . . . . .
H17 H 0.370320 0.613387 0.888578 0.055 Uiso 1 1 calc R . . . .
C18 C 0.3686(2) 0.56108(9) 0.77296(10) 0.0406(3) Uani 1 1 d . . . . .
H18 H 0.318415 0.515280 0.789341 0.049 Uiso 1 1 calc R . . . .
C19 C 0.4104(2) 0.56912(8) 0.69025(9) 0.0324(3) Uani 1 1 d . . . . .
H19 H 0.387324 0.529034 0.649810 0.039 Uiso 1 1 calc R . . . .
C20 C 0.76780(19) 0.53139(7) 0.57128(9) 0.0294(3) Uani 1 1 d . . . . .
C21 C 0.81875(18) 0.51759(7) 0.66762(9) 0.0289(3) Uani 1 1 d . . . . .
C22 C 0.88211(19) 0.57373(7) 0.72811(9) 0.0317(3) Uani 1 1 d . . . . .
H22 H 0.902097 0.622528 0.708212 0.038 Uiso 1 1 calc R . . . .
C23 C 0.9162(2) 0.55874(8) 0.81737(9) 0.0358(3) Uani 1 1 d . . . . .
H23 H 0.959255 0.597181 0.858416 0.043 Uiso 1 1 calc R . . . .
C24 C 0.8873(2) 0.48763(8) 0.84627(9) 0.0383(3) Uani 1 1 d . . . . .
H24 H 0.906918 0.477614 0.907302 0.046 Uiso 1 1 calc R . . . .
C25 C 0.8298(2) 0.43099(8) 0.78659(10) 0.0387(3) Uani 1 1 d . . . . .
H25 H 0.812737 0.382049 0.806808 0.046 Uiso 1 1 calc R . . . .
C26 C 0.7972(2) 0.44544(7) 0.69764(9) 0.0336(3) Uani 1 1 d . . . . .
H26 H 0.760078 0.406254 0.656898 0.040 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 C9 1.2306(16) . ?
O2 C20 1.2353(16) . ?
N1 C4 1.3845(16) . ?
N1 C5 1.3924(16) . ?
N1 C8 1.4032(16) . ?
N2 C6 1.4270(16) . ?
N2 C9 1.4080(17) . ?
N2 C13 1.3800(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3621(19) . ?
C1 C5 1.4110(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.416(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.356(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3920(18) . ?
C6 C7 1.3949(18) . ?
C7 C8 1.4057(18) . ?
C7 C14 1.4811(18) . ?
C8 C20 1.4613(18) . ?
C9 C10 1.4415(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.351(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.414(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.3486(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3945(19) . ?
C14 C19 1.3919(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.4931(19) . ?
C21 C22 1.3932(19) . ?
C21 C26 1.3969(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3894(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(2) . ?
C26 H26 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
C4 N1 C5 120.62(11) . . ?
C4 N1 C8 129.62(11) . . ?
C5 N1 C8 109.62(10) . . ?
C9 N2 C6 118.35(10) . . ?
C13 N2 C6 118.63(11) . . ?
C13 N2 C9 122.92(11) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C5 119.29(13) . . ?
C5 C1 H1 120.4 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.71(13) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.43(13) . . ?
C4 C3 H3 119.3 . . ?
N1 C4 H4 120.4 . . ?
C3 C4 N1 119.12(13) . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C1 119.73(11) . . ?
C6 C5 N1 106.51(11) . . ?
C6 C5 C1 133.76(12) . . ?
C5 C6 N2 125.12(11) . . ?
C5 C6 C7 109.55(11) . . ?
C7 C6 N2 125.22(11) . . ?
C6 C7 C8 107.55(11) . . ?
C6 C7 C14 124.08(11) . . ?
C8 C7 C14 128.29(11) . . ?
N1 C8 C7 106.77(11) . . ?
N1 C8 C20 121.98(11) . . ?
C7 C8 C20 130.50(12) . . ?
O1 C9 N2 119.83(12) . . ?
O1 C9 C10 125.96(13) . . ?
N2 C9 C10 114.21(12) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.03(14) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.10(13) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.42(13) . . ?
C13 C12 H12 120.8 . . ?
N2 C13 H13 119.3 . . ?
C12 C13 N2 121.30(13) . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C7 120.37(12) . . ?
C19 C14 C7 120.57(11) . . ?
C19 C14 C15 119.06(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.11(14) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.09(14) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.08(14) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.32(15) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.32(13) . . ?
C18 C19 H19 119.8 . . ?
O2 C20 C8 121.46(12) . . ?
O2 C20 C21 120.12(12) . . ?
C8 C20 C21 118.37(11) . . ?
C22 C21 C20 122.75(12) . . ?
C22 C21 C26 119.22(12) . . ?
C26 C21 C20 118.01(12) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.36(13) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.77(13) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.26(13) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.22(13) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.09(13) . . ?
C25 C26 H26 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
