# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_20200106ZH_KHAZ0863_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2032795'
loop_
_audit_author_name
_audit_author_address
'zhen zhang'
;Yantai University
China
;
_audit_update_record             
;
2020-09-19 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 N5 O'
_chemical_formula_weight         459.54

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   27.8270(12)
_cell_length_b                   7.9969(4)
_cell_length_c                   24.2837(11)
_cell_angle_alpha                90
_cell_angle_beta                 119.399(2)
_cell_angle_gamma                90
_cell_volume                     4707.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6567
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.05

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22877
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5836
_reflns_number_gt                4316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+2.1283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5836
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.72656(7) 0.4007(2) 0.43111(9) 0.0531(4) Uani 1 1 d . . . . .
H1 H 0.731295 0.282819 0.433674 0.064 Uiso 1 1 calc R U . . .
C2 C 0.76240(8) 0.5006(3) 0.42108(11) 0.0651(6) Uani 1 1 d . . . . .
H2 H 0.791585 0.451038 0.417119 0.078 Uiso 1 1 calc R U . . .
C3 C 0.75559(8) 0.6699(3) 0.41694(9) 0.0626(5) Uani 1 1 d . . . . .
H3 H 0.780041 0.738314 0.410018 0.075 Uiso 1 1 calc R U . . .
C4 C 0.71337(8) 0.7420(3) 0.42275(10) 0.0626(5) Uani 1 1 d . . . . .
H4 H 0.708546 0.859833 0.419464 0.075 Uiso 1 1 calc R U . . .
C5 C 0.67801(7) 0.6431(2) 0.43336(8) 0.0500(4) Uani 1 1 d . . . . .
H5 H 0.649275 0.693710 0.437922 0.060 Uiso 1 1 calc R U . . .
C6 C 0.68408(6) 0.4708(2) 0.43741(7) 0.0375(3) Uani 1 1 d . . . . .
C7 C 0.64468(6) 0.3623(2) 0.44756(7) 0.0370(3) Uani 1 1 d . . . . .
H7A H 0.654209 0.243367 0.446819 0.044 Uiso 1 1 calc R U . . .
H7B H 0.649124 0.386227 0.489813 0.044 Uiso 1 1 calc R U . . .
C8 C 0.54461(7) 0.0471(2) 0.34176(8) 0.0424(4) Uani 1 1 d . . . . .
H8 H 0.523351 0.088913 0.359638 0.051 Uiso 1 1 calc R U . . .
C9 C 0.54535(8) -0.1224(2) 0.33128(9) 0.0583(5) Uani 1 1 d . . . . .
H9 H 0.524744 -0.196738 0.342231 0.070 Uiso 1 1 calc R U . . .
C10 C 0.57576(9) -0.1845(2) 0.30506(9) 0.0653(6) Uani 1 1 d . . . . .
H10 H 0.575898 -0.301053 0.297653 0.078 Uiso 1 1 calc R U . . .
C11 C 0.60587(9) -0.0773(2) 0.28967(8) 0.0581(5) Uani 1 1 d . . . . .
H11 H 0.627133 -0.119962 0.271919 0.070 Uiso 1 1 calc R U . . .
C12 C 0.60534(7) 0.0926(2) 0.29994(7) 0.0416(4) Uani 1 1 d . . . . .
H12 H 0.626031 0.166310 0.288894 0.050 Uiso 1 1 calc R U . . .
C13 C 0.57477(5) 0.15611(17) 0.32627(6) 0.0301(3) Uani 1 1 d . . . . .
C14 C 0.57371(5) 0.34219(17) 0.33519(6) 0.0289(3) Uani 1 1 d . . . . .
H14A H 0.600507 0.396061 0.325124 0.035 Uiso 1 1 calc R U . . .
H14B H 0.536578 0.385259 0.305004 0.035 Uiso 1 1 calc R U . . .
C15 C 0.55317(5) 0.46961(16) 0.41616(6) 0.0281(3) Uani 1 1 d . . . . .
C16 C 0.49345(5) 0.48166(16) 0.37228(6) 0.0278(3) Uani 1 1 d . . . . .
C17 C 0.45763(5) 0.57542(16) 0.38463(6) 0.0268(3) Uani 1 1 d . . . . .
C18 C 0.44361(5) 0.82998(16) 0.43246(6) 0.0279(3) Uani 1 1 d . . . . .
C19 C 0.44144(6) 0.88481(17) 0.48541(7) 0.0335(3) Uani 1 1 d . . . . .
H19 H 0.454893 0.815834 0.521860 0.040 Uiso 1 1 calc R U . . .
C20 C 0.41949(6) 1.04095(19) 0.48476(8) 0.0408(4) Uani 1 1 d . . . . .
H20 H 0.418219 1.079253 0.521056 0.049 Uiso 1 1 calc R U . . .
C21 C 0.39954(7) 1.14079(19) 0.43191(8) 0.0453(4) Uani 1 1 d . . . . .
H21 H 0.384543 1.247625 0.431744 0.054 Uiso 1 1 calc R U . . .
C22 C 0.40137(7) 1.0854(2) 0.37907(8) 0.0455(4) Uani 1 1 d . . . . .
H22 H 0.387251 1.153777 0.342410 0.055 Uiso 1 1 calc R U . . .
C23 C 0.42376(6) 0.93014(18) 0.37940(7) 0.0366(3) Uani 1 1 d . . . . .
H23 H 0.425436 0.892818 0.343244 0.044 Uiso 1 1 calc R U . . .
C24 C 0.34106(6) 0.58144(18) 0.37250(7) 0.0354(3) Uani 1 1 d . . . . .
H24 H 0.368913 0.555662 0.414347 0.042 Uiso 1 1 calc R U . . .
C25 C 0.28751(7) 0.6155(2) 0.35884(9) 0.0487(4) Uani 1 1 d . . . . .
H25 H 0.278387 0.612391 0.391741 0.058 Uiso 1 1 calc R U . . .
C26 C 0.24739(7) 0.6539(3) 0.29830(10) 0.0634(5) Uani 1 1 d . . . . .
H26 H 0.210991 0.678497 0.289848 0.076 Uiso 1 1 calc R U . . .
C27 C 0.25968(7) 0.6568(3) 0.24974(9) 0.0597(5) Uani 1 1 d . . . . .
H27 H 0.231780 0.683117 0.207978 0.072 Uiso 1 1 calc R U . . .
C28 C 0.31266(6) 0.6215(2) 0.26192(7) 0.0423(4) Uani 1 1 d . . . . .
H28 H 0.321357 0.621481 0.228661 0.051 Uiso 1 1 calc R U . . .
C29 C 0.35272(5) 0.58613(17) 0.32314(7) 0.0305(3) Uani 1 1 d . . . . .
N1 N 0.58699(5) 0.38948(15) 0.39955(5) 0.0305(3) Uani 1 1 d . . . . .
N2 N 0.46286(5) 0.40032(15) 0.31611(6) 0.0333(3) Uani 1 1 d . . . . .
N3 N 0.41118(5) 0.43688(15) 0.29278(6) 0.0345(3) Uani 1 1 d . . . . .
N4 N 0.40696(4) 0.54453(14) 0.33481(5) 0.0292(2) Uani 1 1 d . . . . .
N5 N 0.46868(5) 0.67216(14) 0.43578(5) 0.0315(3) Uani 1 1 d . . . . .
H5A H 0.506315 0.665311 0.467538 0.038 Uiso 1 1 d R U . . .
O1 O 0.57095(4) 0.53159(13) 0.46970(4) 0.0355(2) 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
C1 C6 1.383(2) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.364(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(2) . ?
C7 N1 1.4649(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.381(2) . ?
C8 C13 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3871(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.5061(19) . ?
C14 N1 1.4682(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O1 1.2448(16) . ?
C15 N1 1.3533(16) . ?
C15 C16 1.4725(19) . ?
C16 N2 1.3669(17) . ?
C16 C17 1.3925(17) . ?
C17 N4 1.3557(17) . ?
C17 N5 1.3641(16) . ?
C18 C23 1.381(2) . ?
C18 C19 1.3876(18) . ?
C18 N5 1.4251(17) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.385(2) . ?
C24 C29 1.3877(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.383(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.380(2) . ?
C28 H28 0.9500 . ?
C29 N4 1.4316(16) . ?
N2 N3 1.2940(16) . ?
N3 N4 1.3837(15) . ?
N5 H5A 0.9495 . ?

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
C6 C1 C2 120.84(18) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.85(18) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.16(19) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.60(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.43(16) . . ?
C1 C6 C7 120.90(15) . . ?
C5 C6 C7 120.66(14) . . ?
N1 C7 C6 112.62(12) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 120.14(16) . . ?
C9 C8 H8 119.9 . . ?
C13 C8 H8 119.9 . . ?
C10 C9 C8 120.46(18) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.80(17) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.15(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.41(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.04(14) . . ?
C8 C13 C14 121.74(12) . . ?
C12 C13 C14 119.19(13) . . ?
N1 C14 C13 113.27(11) . . ?
N1 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
O1 C15 N1 121.46(13) . . ?
O1 C15 C16 117.29(11) . . ?
N1 C15 C16 121.22(12) . . ?
N2 C16 C17 108.08(12) . . ?
N2 C16 C15 128.30(11) . . ?
C17 C16 C15 123.52(12) . . ?
N4 C17 N5 125.93(11) . . ?
N4 C17 C16 104.50(11) . . ?
N5 C17 C16 129.51(12) . . ?
C23 C18 C19 120.11(13) . . ?
C23 C18 N5 121.79(12) . . ?
C19 C18 N5 118.05(12) . . ?
C20 C19 C18 119.56(14) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.45(14) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.88(14) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.17(15) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 119.82(14) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C29 117.89(15) . . ?
C25 C24 H24 121.1 . . ?
C29 C24 H24 121.1 . . ?
C26 C25 C24 120.89(15) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.38(15) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C28 119.95(17) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 118.98(15) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C24 121.90(13) . . ?
C28 C29 N4 118.44(12) . . ?
C24 C29 N4 119.58(13) . . ?
C15 N1 C7 118.93(11) . . ?
C15 N1 C14 126.22(11) . . ?
C7 N1 C14 114.44(10) . . ?
N3 N2 C16 110.07(11) . . ?
N2 N3 N4 107.23(11) . . ?
C17 N4 N3 110.12(10) . . ?
C17 N4 C29 131.90(11) . . ?
N3 N4 C29 117.50(11) . . ?
C17 N5 C18 124.43(12) . . ?
C17 N5 H5A 111.9 . . ?
C18 N5 H5A 114.3 . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.038



