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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_ww
_database_code_depnum_ccdc_archive 'CCDC 2078187'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2021-04-17 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2020-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H24 N4 O2'
_chemical_formula_sum            'C29 H24 N4 O2'
_chemical_formula_weight         460.52
_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                   11.343(5)
_cell_length_b                   16.715(8)
_cell_length_c                   13.695(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.156(7)
_cell_angle_gamma                90
_cell_volume                     2437.6(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3916
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.59
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0468 before and 0.0294 after correction.
The Ratio of minimum to maximum transmission is 0.9179.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12254
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3132
_reflns_number_total             4288
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.499
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4288
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.025
_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)+(0.0853P)²+1.5448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1770
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C22, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B)
3.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C1(H1), C2(H2), C3(H3A), C4(H4A), C5(H5), C8(H8), C12(H12),
 C13(H13), C14(H14), C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_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 0.23884(14) 0.63086(10) 0.38145(12) 0.0405(4) Uani 1 1 d . . . . .
O2 O 0.2443(2) 0.74162(11) 0.07740(13) 0.0582(5) Uani 1 1 d . . . . .
N1 N 0.57030(17) 0.67632(12) 0.61749(15) 0.0409(5) Uani 1 1 d . . . . .
N2 N 0.6169(2) 0.78127(14) 0.51867(18) 0.0571(6) Uani 1 1 d . . . . .
N3 N 0.2115(2) 0.81336(12) 0.36267(15) 0.0460(5) Uani 1 1 d . . . . .
H3 H 0.2418 0.7817 0.4148 0.055 Uiso 1 1 calc R . . . .
N4 N 0.1892(2) 0.84688(13) 0.19499(17) 0.0572(6) Uani 1 1 d . . . . .
H4 H 0.2075 0.8370 0.1402 0.069 Uiso 1 1 calc R . . . .
C1 C 0.8381(3) 0.8134(2) 0.6880(2) 0.0666(9) Uani 1 1 d . . . . .
H1 H 0.8295 0.8349 0.6233 0.080 Uiso 1 1 calc R . . . .
C2 C 0.9420(3) 0.8326(2) 0.7736(3) 0.0723(9) Uani 1 1 d . . . . .
H2 H 1.0034 0.8663 0.7659 0.087 Uiso 1 1 calc R . . . .
C3 C 0.9549(3) 0.80238(19) 0.8693(2) 0.0623(8) Uani 1 1 d . . . . .
H3A H 1.0253 0.8149 0.9265 0.075 Uiso 1 1 calc R . . . .
C4 C 0.8639(3) 0.75366(19) 0.8804(2) 0.0637(8) Uani 1 1 d . . . . .
H4A H 0.8712 0.7342 0.9459 0.076 Uiso 1 1 calc R . . . .
C5 C 0.7605(3) 0.73291(18) 0.7949(2) 0.0562(7) Uani 1 1 d . . . . .
H5 H 0.6998 0.6989 0.8032 0.067 Uiso 1 1 calc R . . . .
C6 C 0.7471(2) 0.76227(15) 0.6980(2) 0.0464(6) Uani 1 1 d . . . . .
C7 C 0.6380(2) 0.73869(15) 0.6058(2) 0.0447(6) Uani 1 1 d . . . . .
C8 C 0.5177(2) 0.75933(16) 0.4369(2) 0.0501(7) Uani 1 1 d . . . . .
H8 H 0.4996 0.7880 0.3753 0.060 Uiso 1 1 calc R . . . .
C9 C 0.4414(2) 0.69640(14) 0.43977(17) 0.0357(5) Uani 1 1 d . . . . .
C10 C 0.4729(2) 0.65493(14) 0.53370(17) 0.0351(5) Uani 1 1 d . . . . .
C11 C 0.3978(2) 0.58500(14) 0.53888(18) 0.0357(5) Uani 1 1 d . . . . .
C12 C 0.4352(2) 0.52786(15) 0.6177(2) 0.0483(6) Uani 1 1 d . . . . .
H12 H 0.5118 0.5336 0.6714 0.058 Uiso 1 1 calc R . . . .
C13 C 0.3602(3) 0.46328(17) 0.6170(2) 0.0614(8) Uani 1 1 d . . . . .
H13 H 0.3866 0.4250 0.6693 0.074 Uiso 1 1 calc R . . . .
C14 C 0.2459(3) 0.45528(18) 0.5387(3) 0.0674(9) Uani 1 1 d . . . . .
H14 H 0.1952 0.4114 0.5383 0.081 Uiso 1 1 calc R . . . .
C15 C 0.2818(2) 0.57567(14) 0.45994(18) 0.0383(5) Uani 1 1 d . . . . .
C16 C 0.2055(3) 0.51174(17) 0.4606(2) 0.0579(8) Uani 1 1 d . . . . .
H16 H 0.1273 0.5066 0.4087 0.069 Uiso 1 1 calc R . . . .
C17 C 0.3372(2) 0.66441(14) 0.34658(17) 0.0362(5) Uani 1 1 d . . . . .
H17 H 0.3726 0.6196 0.3196 0.043 Uiso 1 1 calc R . . . .
C18 C 0.2808(2) 0.72035(14) 0.25767(17) 0.0368(5) Uani 1 1 d . . . . .
C19 C 0.2757(2) 0.69709(15) 0.15790(18) 0.0427(6) Uani 1 1 d . . . . .
C20 C 0.3033(3) 0.61210(17) 0.14013(19) 0.0518(7) Uani 1 1 d . . . . .
C21 C 0.4078(4) 0.5910(3) 0.1181(3) 0.0872(12) Uani 1 1 d . . . . .
H21 H 0.4683 0.6288 0.1191 0.105 Uiso 1 1 calc R . . . .
C22 C 0.4220(6) 0.5081(3) 0.0930(3) 0.1208(19) Uani 1 1 d . U . . .
H22 H 0.4922 0.4908 0.0785 0.145 Uiso 1 1 calc R . . . .
C23 C 0.2265(6) 0.4766(2) 0.1124(3) 0.1086(16) Uani 1 1 d . . . . .
H23 H 0.1651 0.4389 0.1096 0.130 Uiso 1 1 calc R . . . .
C24 C 0.3283(7) 0.4563(3) 0.0915(3) 0.1210(19) Uani 1 1 d . U . . .
H24 H 0.3365 0.4032 0.0746 0.145 Uiso 1 1 calc R . . . .
C25 C 0.2145(4) 0.55391(18) 0.1381(3) 0.0747(10) Uani 1 1 d . . . . .
H25 H 0.1447 0.5685 0.1549 0.090 Uiso 1 1 calc R . . . .
C26 C 0.2275(2) 0.79477(14) 0.27309(17) 0.0398(6) Uani 1 1 d . . . . .
C27 C 0.1189(4) 0.9190(2) 0.1959(3) 0.0794(11) Uani 1 1 d . . . . .
H27A H 0.0555 0.9271 0.1280 0.095 Uiso 1 1 calc R . . . .
H27B H 0.1750 0.9647 0.2111 0.095 Uiso 1 1 calc R . . . .
C28 C 0.0582(4) 0.9128(2) 0.2752(3) 0.0965(14) Uani 1 1 d . . . . .
H28A H 0.0257 0.9648 0.2845 0.116 Uiso 1 1 calc R . . . .
H28B H -0.0122 0.8761 0.2508 0.116 Uiso 1 1 calc R . . . .
C29 C 0.1455(3) 0.88458(18) 0.3758(2) 0.0607(8) Uani 1 1 d . . . . .
H29A H 0.2057 0.9264 0.4077 0.073 Uiso 1 1 calc R . . . .
H29B H 0.0991 0.8728 0.4218 0.073 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 C15 1.372(3) . ?
O1 C17 1.468(3) . ?
O2 C19 1.275(3) . ?
N1 C7 1.337(3) . ?
N1 C10 1.339(3) . ?
N2 C7 1.338(3) . ?
N2 C8 1.337(3) . ?
N3 H3 0.8600 . ?
N3 C26 1.337(3) . ?
N3 C29 1.451(3) . ?
N4 H4 0.8600 . ?
N4 C26 1.331(3) . ?
N4 C27 1.448(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(4) . ?
C1 C6 1.383(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.364(4) . ?
C4 H4A 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(4) . ?
C6 C7 1.484(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(3) . ?
C9 C10 1.395(3) . ?
C9 C17 1.508(3) . ?
C10 C11 1.462(3) . ?
C11 C12 1.394(3) . ?
C11 C15 1.394(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9300 . ?
C14 C16 1.381(4) . ?
C15 C16 1.377(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9800 . ?
C17 C18 1.493(3) . ?
C18 C19 1.403(3) . ?
C18 C26 1.430(3) . ?
C19 C20 1.493(4) . ?
C20 C21 1.367(4) . ?
C20 C25 1.394(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.449(6) . ?
C22 H22 0.9300 . ?
C22 C24 1.364(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.326(7) . ?
C23 C25 1.359(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.476(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.470(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?

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
C15 O1 C17 114.02(17) . . ?
C7 N1 C10 116.4(2) . . ?
C8 N2 C7 116.2(2) . . ?
C26 N3 H3 118.5 . . ?
C26 N3 C29 122.9(2) . . ?
C29 N3 H3 118.5 . . ?
C26 N4 H4 117.8 . . ?
C26 N4 C27 124.5(2) . . ?
C27 N4 H4 117.8 . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3A 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 H4A 119.7 . . ?
C3 C4 C5 120.5(3) . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 120.7(2) . . ?
N1 C7 N2 126.0(2) . . ?
N1 C7 C6 116.7(2) . . ?
N2 C7 C6 117.3(2) . . ?
N2 C8 H8 118.5 . . ?
N2 C8 C9 122.9(2) . . ?
C9 C8 H8 118.5 . . ?
C8 C9 C10 116.4(2) . . ?
C8 C9 C17 124.5(2) . . ?
C10 C9 C17 118.8(2) . . ?
N1 C10 C9 122.1(2) . . ?
N1 C10 C11 119.6(2) . . ?
C9 C10 C11 118.3(2) . . ?
C12 C11 C10 124.0(2) . . ?
C12 C11 C15 118.6(2) . . ?
C15 C11 C10 117.5(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C16 120.6(3) . . ?
C16 C14 H14 119.7 . . ?
O1 C15 C11 121.2(2) . . ?
O1 C15 C16 118.2(2) . . ?
C16 C15 C11 120.6(2) . . ?
C14 C16 H16 120.2 . . ?
C15 C16 C14 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
O1 C17 C9 108.81(18) . . ?
O1 C17 H17 106.7 . . ?
O1 C17 C18 110.15(18) . . ?
C9 C17 H17 106.7 . . ?
C18 C17 C9 117.3(2) . . ?
C18 C17 H17 106.7 . . ?
C19 C18 C17 118.9(2) . . ?
C19 C18 C26 120.5(2) . . ?
C26 C18 C17 120.6(2) . . ?
O2 C19 C18 125.9(2) . . ?
O2 C19 C20 115.2(2) . . ?
C18 C19 C20 118.8(2) . . ?
C21 C20 C19 121.9(3) . . ?
C21 C20 C25 119.4(3) . . ?
C25 C20 C19 118.4(3) . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C22 118.3(4) . . ?
C22 C21 H21 120.8 . . ?
C21 C22 H22 121.3 . . ?
C24 C22 C21 117.4(4) . . ?
C24 C22 H22 121.3 . . ?
C24 C23 H23 120.9 . . ?
C24 C23 C25 118.1(5) . . ?
C25 C23 H23 120.9 . . ?
C22 C24 H24 117.8 . . ?
C23 C24 C22 124.5(5) . . ?
C23 C24 H24 117.8 . . ?
C20 C25 H25 118.9 . . ?
C23 C25 C20 122.2(4) . . ?
C23 C25 H25 118.9 . . ?
N3 C26 C18 122.4(2) . . ?
N4 C26 N3 118.4(2) . . ?
N4 C26 C18 119.2(2) . . ?
N4 C27 H27A 109.6 . . ?
N4 C27 H27B 109.6 . . ?
N4 C27 C28 110.2(3) . . ?
H27A C27 H27B 108.1 . . ?
C28 C27 H27A 109.6 . . ?
C28 C27 H27B 109.6 . . ?
C27 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C29 C28 C27 112.2(3) . . ?
C29 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
N3 C29 C28 110.9(2) . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
