# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zyy
_database_code_depnum_ccdc_archive 'CCDC 2158085'
loop_
_audit_author_name
_audit_author_address
zhangyingying
;GuangXi Unversity
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_audit_creation_date             2022-03-08
_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         'C25 H19 N3 O'
_chemical_formula_sum            'C25 H19 N3 O'
_chemical_formula_weight         377.43
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.6523(15)
_cell_length_b                   8.3706(5)
_cell_length_c                   25.8377(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.543(8)
_cell_angle_gamma                90
_cell_volume                     3904.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3853
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.3270
_cell_measurement_theta_min      3.8210
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.41'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14957
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.456
_diffrn_reflns_theta_min         3.816
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                3261
_reflns_number_total             4646
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0051(5)
_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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.032
_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)+(0.0626P)²+2.2875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1555
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.91494(8) 0.67354(17) 0.47948(7) 0.0780(5) Uani 1 1 d . . . . .
N1 N 0.71041(8) 1.00543(17) 0.29240(6) 0.0495(4) Uani 1 1 d . . . . .
N2 N 0.62695(8) 0.92998(18) 0.34566(6) 0.0510(4) Uani 1 1 d . . . . .
N3 N 0.57773(12) 0.8128(3) 0.32888(10) 0.0905(7) Uani 1 1 d . . . . .
C1 C 0.65538(13) 1.0784(3) 0.24888(9) 0.0823(7) Uani 1 1 d . . . . .
H1A H 0.658104 1.030939 0.215597 0.123 Uiso 1 1 calc GR . . . .
H1B H 0.664779 1.190965 0.247982 0.123 Uiso 1 1 calc GR . . . .
H1C H 0.606883 1.061400 0.254300 0.123 Uiso 1 1 calc GR . . . .
C2 C 0.69809(9) 0.92886(19) 0.33663(7) 0.0437(4) Uani 1 1 d . . . . .
C3 C 0.76138(9) 0.86650(18) 0.36783(6) 0.0383(4) Uani 1 1 d . . . . .
C4 C 0.81824(9) 0.90680(18) 0.34185(6) 0.0398(4) Uani 1 1 d . . . . .
C5 C 0.89444(10) 0.8811(2) 0.35332(7) 0.0486(4) Uani 1 1 d . . . . .
H5 H 0.918461 0.824986 0.383814 0.058 Uiso 1 1 calc R . . . .
C6 C 0.93358(11) 0.9398(3) 0.31900(8) 0.0632(5) Uani 1 1 d . . . . .
H6 H 0.984295 0.921286 0.326265 0.076 Uiso 1 1 calc R . . . .
C7 C 0.89902(13) 1.0263(3) 0.27358(9) 0.0705(6) Uani 1 1 d . . . . .
H7 H 0.927133 1.065300 0.251301 0.085 Uiso 1 1 calc R . . . .
C8 C 0.82498(13) 1.0546(2) 0.26122(8) 0.0631(6) Uani 1 1 d . . . . .
H8 H 0.802062 1.113161 0.230996 0.076 Uiso 1 1 calc R . . . .
C9 C 0.78447(10) 0.9935(2) 0.29519(6) 0.0458(4) Uani 1 1 d . . . . .
C10 C 0.59913(14) 1.0458(3) 0.36973(15) 0.1039(11) Uani 1 1 d . . . . .
H10 H 0.623254 1.138007 0.385047 0.125 Uiso 1 1 calc R . . . .
C11 C 0.52901(17) 1.0030(4) 0.36747(17) 0.1157(12) Uani 1 1 d . . . . .
H11 H 0.494671 1.061704 0.380169 0.139 Uiso 1 1 calc R . . . .
C12 C 0.51787(14) 0.8619(4) 0.34387(14) 0.1005(10) Uani 1 1 d . . . . .
H12 H 0.473991 0.804232 0.338397 0.121 Uiso 1 1 calc R . . . .
C13 C 0.76893(9) 0.77597(19) 0.41957(6) 0.0401(4) Uani 1 1 d . . . . .
H13 H 0.719352 0.764475 0.425566 0.048 Uiso 1 1 calc R . . . .
C14 C 0.81610(9) 0.86636(19) 0.46631(6) 0.0404(4) Uani 1 1 d . . . . .
C15 C 0.79219(12) 1.0084(2) 0.48337(7) 0.0573(5) Uani 1 1 d . . . . .
H15 H 0.744961 1.045386 0.466895 0.069 Uiso 1 1 calc R . . . .
C16 C 0.83610(14) 1.0966(3) 0.52397(8) 0.0714(6) Uani 1 1 d . . . . .
H16 H 0.818686 1.192270 0.534482 0.086 Uiso 1 1 calc R . . . .
C17 C 0.90531(14) 1.0436(3) 0.54883(9) 0.0757(7) Uani 1 1 d . . . . .
H17 H 0.935511 1.103581 0.576054 0.091 Uiso 1 1 calc R . . . .
C18 C 0.93002(13) 0.9020(3) 0.53351(9) 0.0747(7) Uani 1 1 d . . . . .
H18 H 0.976959 0.864632 0.550576 0.090 Uiso 1 1 calc R . . . .
C19 C 0.88530(10) 0.8145(2) 0.49274(7) 0.0526(5) Uani 1 1 d . . . . .
C20 C 0.86880(11) 0.5681(2) 0.44581(8) 0.0535(5) Uani 1 1 d . . . . .
C21 C 0.89772(13) 0.4165(2) 0.44259(10) 0.0716(6) Uani 1 1 d . . . . .
H21 H 0.944619 0.390357 0.463332 0.086 Uiso 1 1 calc R . . . .
C22 C 0.85699(14) 0.3068(3) 0.40893(10) 0.0754(7) Uani 1 1 d . . . . .
H22 H 0.876236 0.205412 0.406359 0.090 Uiso 1 1 calc R . . . .
C23 C 0.78804(15) 0.3448(2) 0.37894(10) 0.0739(7) Uani 1 1 d . . . . .
H23 H 0.760340 0.269554 0.355841 0.089 Uiso 1 1 calc R . . . .
C24 C 0.75928(12) 0.4950(2) 0.38283(8) 0.0585(5) Uani 1 1 d . . . . .
H24 H 0.711805 0.519320 0.362700 0.070 Uiso 1 1 calc R . . . .
C25 C 0.79982(10) 0.60982(19) 0.41611(7) 0.0426(4) 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 C19 1.382(2) . ?
O1 C20 1.379(2) . ?
N1 C1 1.453(2) . ?
N1 C2 1.379(2) . ?
N1 C9 1.369(2) . ?
N2 N3 1.339(2) . ?
N2 C2 1.404(2) . ?
N2 C10 1.326(3) . ?
N3 C12 1.335(3) . ?
C2 C3 1.356(2) . ?
C3 C4 1.431(2) . ?
C3 C13 1.512(2) . ?
C4 C5 1.394(2) . ?
C4 C9 1.412(2) . ?
C5 C6 1.373(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.358(3) . ?
C8 C9 1.392(3) . ?
C10 C11 1.343(4) . ?
C11 C12 1.321(4) . ?
C13 C14 1.507(2) . ?
C13 C25 1.517(2) . ?
C14 C15 1.380(2) . ?
C14 C19 1.371(2) . ?
C15 C16 1.373(3) . ?
C16 C17 1.363(3) . ?
C17 C18 1.366(3) . ?
C18 C19 1.379(3) . ?
C20 C21 1.389(3) . ?
C20 C25 1.368(3) . ?
C21 C22 1.359(3) . ?
C22 C23 1.362(3) . ?
C23 C24 1.381(3) . ?
C24 C25 1.381(3) . ?

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
C20 O1 C19 118.55(14) . . ?
C2 N1 C1 127.18(18) . . ?
C9 N1 C1 125.39(17) . . ?
C9 N1 C2 107.36(13) . . ?
N3 N2 C2 122.77(16) . . ?
C10 N2 N3 111.73(19) . . ?
C10 N2 C2 125.47(17) . . ?
C12 N3 N2 103.7(2) . . ?
N1 C2 N2 119.72(15) . . ?
C3 C2 N1 111.73(15) . . ?
C3 C2 N2 128.47(16) . . ?
C2 C3 C4 105.52(14) . . ?
C2 C3 C13 126.33(15) . . ?
C4 C3 C13 128.14(14) . . ?
C5 C4 C3 134.45(15) . . ?
C5 C4 C9 118.24(16) . . ?
C9 C4 C3 107.30(15) . . ?
C6 C5 C4 119.12(17) . . ?
C5 C6 C7 121.5(2) . . ?
C8 C7 C6 121.18(19) . . ?
C7 C8 C9 117.93(19) . . ?
N1 C9 C4 108.08(15) . . ?
N1 C9 C8 129.83(17) . . ?
C8 C9 C4 122.06(18) . . ?
N2 C10 C11 106.0(2) . . ?
C12 C11 C10 107.3(2) . . ?
C11 C12 N3 111.3(2) . . ?
C3 C13 C25 111.08(13) . . ?
C14 C13 C3 111.27(13) . . ?
C14 C13 C25 110.72(13) . . ?
C15 C14 C13 121.20(15) . . ?
C19 C14 C13 121.83(15) . . ?
C19 C14 C15 116.94(16) . . ?
C16 C15 C14 121.92(18) . . ?
C17 C16 C15 119.84(19) . . ?
C16 C17 C18 119.6(2) . . ?
C17 C18 C19 119.9(2) . . ?
C14 C19 O1 122.16(16) . . ?
C14 C19 C18 121.72(17) . . ?
C18 C19 O1 116.11(17) . . ?
O1 C20 C21 115.62(17) . . ?
C25 C20 O1 122.73(16) . . ?
C25 C20 C21 121.63(19) . . ?
C22 C21 C20 119.5(2) . . ?
C21 C22 C23 120.2(2) . . ?
C22 C23 C24 120.0(2) . . ?
C23 C24 C25 121.1(2) . . ?
C20 C25 C13 121.26(15) . . ?
C20 C25 C24 117.54(16) . . ?
C24 C25 C13 121.20(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
