# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_184
_database_code_depnum_ccdc_archive 'CCDC 2180989'
loop_
_audit_author_name
_audit_author_address
'Songlin Fang'
;JiNan University
China
;
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2023-08-29 downloaded from the CCDC.
;
_audit_creation_date             2022-01-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        3n
_chemical_formula_moiety         'C21 H16 N4 O'
_chemical_formula_sum            'C21 H16 N4 O'
_chemical_formula_weight         340.38
_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      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                   32.257(5)
_cell_length_b                   6.2874(5)
_cell_length_c                   17.439(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.904(14)
_cell_angle_gamma                90
_cell_volume                     3433.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2519
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      73.0730
_cell_measurement_theta_min      2.7970
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11406
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.070
_diffrn_reflns_theta_min         2.822
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  33.00   1.00   10.00    --  -40.73  40.00  79.00   96
  2  ω    -33.00  -2.00   1.00   10.00    --  -40.73 125.00 150.00   31
  3  ω      1.00  61.00   1.00   10.00    --   40.73 -99.00 150.00   60
  4  ω     57.00  96.00   1.00   10.00    --   40.73-125.00  30.00   39
  5  ω     39.00  66.00   1.00    6.00    --  107.58 -45.00 150.00   27
  6  ω     89.00 116.00   1.00    6.00    --  107.58 -45.00 150.00   27
  7  ω     86.00 114.00   1.00    6.00    --  107.58 -45.00  30.00   28
  8  ω     82.00 107.00   1.00    6.00    --  107.58 -95.00 -60.00   25
  9  ω     45.00 119.00   1.00    6.00    --  107.58 -30.00   0.00   74
 10  ω     82.00 174.00   1.00    6.00    --  107.58  45.00 -60.00   92
 11  ω     90.00 115.00   1.00   10.00    --   40.73  38.00-180.00   25
 12  ω     37.00 136.00   1.00    6.00    --  107.58 -30.00 -90.00   99
 13  ω     90.00 117.00   1.00    6.00    --  107.58-125.00  90.00   27
 14  ω     42.00 133.00   1.00    6.00    --  107.58 -77.00   0.00   91
 15  ω     42.00 122.00   1.00    6.00    --  107.58-125.00-150.00   80
 16  ω     37.00 136.00   1.00    6.00    --  107.58 -77.00-150.00   99
 17  ω     33.00  60.00   1.00   10.00    --   40.73  38.00-180.00   27
 18  ω     23.00  80.00   1.00   10.00    --   40.73-125.00 -90.00   57
 19  ω     29.00 157.00   1.00    6.00    --  107.58 -15.00 120.00  128
 20  ω   -113.00 -16.00   1.00   10.00    --  -40.73 -38.00 -90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0153444000
_diffrn_orient_matrix_UB_12      -0.0128838000
_diffrn_orient_matrix_UB_13      -0.0770643000
_diffrn_orient_matrix_UB_21      0.0459636000
_diffrn_orient_matrix_UB_22      0.0498286000
_diffrn_orient_matrix_UB_23      0.0463581000
_diffrn_orient_matrix_UB_31      0.0086615000
_diffrn_orient_matrix_UB_32      -0.2394121000
_diffrn_orient_matrix_UB_33      0.0138527000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2342
_reflns_number_total             3400
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.105
_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)+(0.0540P)²+0.8717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1543
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C19(H19), C8(H8), C20(H20), C9(H9), C10(H10), C16(H16), C1(H1),
 C17(H17), C5(H5), C18(H18), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.10668(6) 0.1583(3) 0.02987(11) 0.0565(5) Uani 1 1 d . . . . .
N2 N 0.17955(6) 0.2320(3) -0.01285(11) 0.0397(5) Uani 1 1 d . . . . .
N1 N 0.20954(6) 0.2154(3) 0.05388(11) 0.0400(5) Uani 1 1 d . . . . .
C7 C 0.05989(7) -0.4263(4) -0.14597(13) 0.0409(6) Uani 1 1 d . . . . .
N4 N 0.19874(7) 0.5495(3) 0.01179(12) 0.0482(5) Uani 1 1 d . . . . .
C12 C 0.08991(7) -0.2729(3) -0.11204(13) 0.0398(5) Uani 1 1 d . . . . .
H12 H 0.1157 -0.2657 -0.1269 0.048 Uiso 1 1 calc R U . . .
C13 C 0.11297(7) 0.0383(4) -0.02072(14) 0.0403(5) Uani 1 1 d . . . . .
C21 C 0.22133(7) 0.4180(3) 0.06779(13) 0.0370(5) Uani 1 1 d . . . . .
C19 C 0.30365(7) 0.7585(4) 0.20067(15) 0.0454(6) Uani 1 1 d . . . . .
H19 H 0.3143 0.8961 0.2021 0.054 Uiso 1 1 calc R U . . .
C8 C 0.02159(8) -0.4346(4) -0.12237(14) 0.0469(6) Uani 1 1 d . . . . .
H8 H 0.0012 -0.5362 -0.1443 0.056 Uiso 1 1 calc R U . . .
N3 N 0.17222(7) 0.4287(3) -0.03928(12) 0.0499(5) Uani 1 1 d . . . . .
C20 C 0.27085(7) 0.6959(4) 0.13791(14) 0.0414(6) Uani 1 1 d . . . . .
H20 H 0.2591 0.7919 0.0980 0.050 Uiso 1 1 calc R U . . .
C9 C 0.01345(8) -0.2941(4) -0.06693(15) 0.0520(7) Uani 1 1 d . . . . .
H9 H -0.0122 -0.3026 -0.0516 0.062 Uiso 1 1 calc R U . . .
C6 C 0.06805(8) -0.5725(4) -0.20794(14) 0.0446(6) Uani 1 1 d . . . . .
C15 C 0.25548(7) 0.4879(4) 0.13478(13) 0.0383(5) Uani 1 1 d . . . . .
C10 C 0.04302(8) -0.1415(4) -0.03417(15) 0.0478(6) Uani 1 1 d . . . . .
H10 H 0.0372 -0.0460 0.0026 0.057 Uiso 1 1 calc R U . . .
C11 C 0.08189(7) -0.1306(4) -0.05636(13) 0.0395(5) Uani 1 1 d . . . . .
C16 C 0.27283(7) 0.3476(4) 0.19574(15) 0.0453(6) Uani 1 1 d . . . . .
H16 H 0.2627 0.2088 0.1943 0.054 Uiso 1 1 calc R U . . .
C14 C 0.15374(7) 0.0545(4) -0.04995(14) 0.0421(6) Uani 1 1 d . . . . .
H14A H 0.1700 -0.0763 -0.0379 0.050 Uiso 1 1 calc R U . . .
H14B H 0.1465 0.0733 -0.1068 0.050 Uiso 1 1 calc R U . . .
C1 C 0.08907(8) -0.5017(5) -0.26367(15) 0.0516(7) Uani 1 1 d . . . . .
H1 H 0.0995 -0.3633 -0.2608 0.062 Uiso 1 1 calc R U . . .
C17 C 0.30502(8) 0.4147(4) 0.25835(15) 0.0502(7) Uani 1 1 d . . . . .
H17 H 0.3164 0.3209 0.2993 0.060 Uiso 1 1 calc R U . . .
C5 C 0.05287(8) -0.7792(4) -0.21280(16) 0.0525(7) Uani 1 1 d . . . . .
H5 H 0.0385 -0.8287 -0.1760 0.063 Uiso 1 1 calc R U . . .
C18 C 0.32055(8) 0.6200(4) 0.26074(15) 0.0491(6) Uani 1 1 d . . . . .
H18 H 0.3424 0.6640 0.3029 0.059 Uiso 1 1 calc R U . . .
C2 C 0.09474(9) -0.6346(5) -0.32371(17) 0.0633(8) Uani 1 1 d . . . . .
H2 H 0.1085 -0.5850 -0.3613 0.076 Uiso 1 1 calc R U . . .
C4 C 0.05899(10) -0.9129(4) -0.27257(18) 0.0635(8) Uani 1 1 d . . . . .
H4 H 0.0489 -1.0519 -0.2754 0.076 Uiso 1 1 calc R U . . .
C3 C 0.07986(10) -0.8406(5) -0.32745(19) 0.0676(9) Uani 1 1 d . . . . .
H3 H 0.0839 -0.9309 -0.3672 0.081 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 C13 1.214(3) . ?
N2 N1 1.327(3) . ?
N2 N3 1.321(2) . ?
N2 C14 1.449(3) . ?
N1 C21 1.335(3) . ?
C7 C12 1.393(3) . ?
C7 C8 1.394(3) . ?
C7 C6 1.490(3) . ?
N4 C21 1.351(3) . ?
N4 N3 1.318(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.390(3) . ?
C13 C11 1.490(3) . ?
C13 C14 1.524(3) . ?
C21 C15 1.467(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(3) . ?
C19 C18 1.370(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C20 H20 0.9300 . ?
C20 C15 1.395(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C6 C1 1.385(4) . ?
C6 C5 1.384(3) . ?
C15 C16 1.391(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.400(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 H1 0.9300 . ?
C1 C2 1.386(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(4) . ?
C18 H18 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.373(4) . ?
C3 H3 0.9300 . ?

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
N1 N2 C14 123.44(18) . . ?
N3 N2 N1 114.28(18) . . ?
N3 N2 C14 122.00(19) . . ?
N2 N1 C21 101.56(17) . . ?
C12 C7 C6 120.6(2) . . ?
C8 C7 C12 118.4(2) . . ?
C8 C7 C6 121.0(2) . . ?
N3 N4 C21 106.60(18) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
O1 C13 C11 122.2(2) . . ?
O1 C13 C14 120.7(2) . . ?
C11 C13 C14 117.15(19) . . ?
N1 C21 N4 111.8(2) . . ?
N1 C21 C15 123.9(2) . . ?
N4 C21 C15 124.3(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.8(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
N4 N3 N2 105.72(19) . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C15 119.6(2) . . ?
C15 C20 H20 120.2 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 C1 119.0(2) . . ?
C20 C15 C21 120.3(2) . . ?
C16 C15 C21 120.4(2) . . ?
C16 C15 C20 119.4(2) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C13 122.1(2) . . ?
C12 C11 C10 119.4(2) . . ?
C10 C11 C13 118.5(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
N2 C14 C13 110.58(18) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C6 C1 H1 119.6 . . ?
C6 C1 C2 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?

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
O1 C13 C11 C12 -177.5(2) . . . . ?
O1 C13 C11 C10 4.2(4) . . . . ?
O1 C13 C14 N2 -3.3(3) . . . . ?
N2 N1 C21 N4 0.7(2) . . . . ?
N2 N1 C21 C15 -177.8(2) . . . . ?
N1 N2 N3 N4 0.5(3) . . . . ?
N1 N2 C14 C13 91.0(2) . . . . ?
N1 C21 C15 C20 169.0(2) . . . . ?
N1 C21 C15 C16 -11.0(3) . . . . ?
C7 C12 C11 C13 -178.4(2) . . . . ?
C7 C12 C11 C10 -0.1(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C7 C6 C1 C2 -176.7(2) . . . . ?
C7 C6 C5 C4 177.4(2) . . . . ?
N4 C21 C15 C20 -9.4(3) . . . . ?
N4 C21 C15 C16 170.6(2) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
C12 C7 C6 C1 -36.7(3) . . . . ?
C12 C7 C6 C5 146.3(2) . . . . ?
C21 N4 N3 N2 0.0(3) . . . . ?
C21 C15 C16 C17 179.8(2) . . . . ?
C19 C20 C15 C21 -178.7(2) . . . . ?
C19 C20 C15 C16 1.3(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C7 C6 C1 141.2(2) . . . . ?
C8 C7 C6 C5 -35.8(3) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
N3 N2 N1 C21 -0.7(2) . . . . ?
N3 N2 C14 C13 -82.5(3) . . . . ?
N3 N4 C21 N1 -0.5(3) . . . . ?
N3 N4 C21 C15 178.0(2) . . . . ?
C20 C19 C18 C17 0.7(4) . . . . ?
C20 C15 C16 C17 -0.2(3) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C9 C10 C11 C13 179.1(2) . . . . ?
C6 C7 C12 C11 177.6(2) . . . . ?
C6 C7 C8 C9 -177.7(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C6 C5 C4 C3 -0.4(4) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C11 C13 C14 N2 177.12(19) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C14 N2 N1 C21 -174.7(2) . . . . ?
C14 N2 N3 N4 174.5(2) . . . . ?
C14 C13 C11 C12 2.1(3) . . . . ?
C14 C13 C11 C10 -176.3(2) . . . . ?
C1 C6 C5 C4 0.4(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C5 C6 C1 C2 0.3(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C18 C19 C20 C15 -1.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.602
_oxdiff_exptl_absorpt_empirical_full_min 0.487
####################################################################### 
# 
# 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_daguan
_database_code_depnum_ccdc_archive 'CCDC 2180990'
loop_
_audit_author_name
_audit_author_address
'Songlin Fang'
;JiNan University
China
;
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2023-08-29 downloaded from the CCDC.
;
_audit_creation_date             2022-01-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N4 O'
_chemical_formula_sum            'C15 H12 N4 O'
_chemical_formula_weight         264.29
_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                   12.6720(9)
_cell_length_b                   11.9871(7)
_cell_length_c                   9.0695(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.184(9)
_cell_angle_gamma                90
_cell_volume                     1293.07(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3723
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.9180
_cell_measurement_theta_min      2.9560
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9622
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.420
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  40.00   1.00    2.00    --   11.90 -57.00-120.00   93
  2  ω    -14.00  78.00   1.00    2.00    --   11.90  77.00 150.00   92
  3  ω     -9.00  85.00   1.00    2.00    --   11.90  57.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0331786000
_diffrn_orient_matrix_UB_12      -0.0027448000
_diffrn_orient_matrix_UB_13      -0.0488300000
_diffrn_orient_matrix_UB_21      -0.0472487000
_diffrn_orient_matrix_UB_22      -0.0198361000
_diffrn_orient_matrix_UB_23      -0.0626555000
_diffrn_orient_matrix_UB_31      -0.0151228000
_diffrn_orient_matrix_UB_32      0.0557168000
_diffrn_orient_matrix_UB_33      -0.0248045000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2447
_reflns_number_total             3185
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0159(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.031
_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)+(0.0392P)²+0.2828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C10(H10), C4(H4), C2(H2), C14(H14), C11(H11), C3(H3),
 C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.33562(8) 0.05145(9) 0.50044(12) 0.0420(3) Uani 1 1 d . . . . .
N1 N 0.06485(9) 0.07599(9) 0.39063(13) 0.0285(3) Uani 1 1 d . . . . .
C7 C 0.31939(10) 0.02553(11) 0.62006(16) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.14225(8) 0.12670(9) 0.50999(13) 0.0297(3) Uani 1 1 d . . . . .
C9 C -0.05626(10) 0.14630(11) 0.13223(16) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.39801(10) -0.04656(10) 0.74242(15) 0.0265(3) Uani 1 1 d . . . . .
C15 C 0.03153(10) 0.15854(10) 0.28685(16) 0.0272(3) Uani 1 1 d . . . . .
N3 N 0.15841(9) 0.23284(9) 0.48380(15) 0.0370(3) Uani 1 1 d . . . . .
C5 C 0.37569(10) -0.08173(11) 0.87491(16) 0.0299(3) Uani 1 1 d . . . . .
H5 H 0.3114 -0.0567 0.8920 0.036 Uiso 1 1 calc R U . . .
N4 N 0.08764(10) 0.25476(9) 0.34156(15) 0.0354(3) Uani 1 1 d . . . . .
C8 C 0.21329(11) 0.06730(11) 0.64696(16) 0.0312(3) Uani 1 1 d . . . . .
H8A H 0.1724 0.0045 0.6681 0.037 Uiso 1 1 calc R U . . .
H8B H 0.2341 0.1164 0.7375 0.037 Uiso 1 1 calc R U . . .
C1 C 0.49638(11) -0.08247(11) 0.71972(17) 0.0325(3) Uani 1 1 d . . . . .
H1 H 0.5126 -0.0586 0.6323 0.039 Uiso 1 1 calc R U . . .
C10 C -0.09163(10) 0.04061(11) 0.07100(17) 0.0306(3) Uani 1 1 d . . . . .
H10 H -0.0604 -0.0225 0.1293 0.037 Uiso 1 1 calc R U . . .
C4 C 0.44860(11) -0.15373(12) 0.98134(17) 0.0352(3) Uani 1 1 d . . . . .
H4 H 0.4329 -0.1777 1.0691 0.042 Uiso 1 1 calc R U . . .
C2 C 0.56928(11) -0.15336(12) 0.82736(18) 0.0367(3) Uani 1 1 d . . . . .
H2 H 0.6350 -0.1765 0.8127 0.044 Uiso 1 1 calc R U . . .
C14 C -0.10476(11) 0.24030(11) 0.04421(17) 0.0353(3) Uani 1 1 d . . . . .
H14 H -0.0827 0.3113 0.0842 0.042 Uiso 1 1 calc R U . . .
C11 C -0.17304(11) 0.02916(13) -0.07621(18) 0.0378(3) Uani 1 1 d . . . . .
H11 H -0.1960 -0.0416 -0.1166 0.045 Uiso 1 1 calc R U . . .
C3 C 0.54530(11) -0.19016(12) 0.95671(18) 0.0371(3) Uani 1 1 d . . . . .
H3 H 0.5939 -0.2393 1.0273 0.044 Uiso 1 1 calc R U . . .
C12 C -0.22019(12) 0.12219(14) -0.16309(18) 0.0432(4) Uani 1 1 d . . . . .
H12 H -0.2749 0.1144 -0.2620 0.052 Uiso 1 1 calc R U . . .
C13 C -0.18576(13) 0.22736(14) -0.10260(19) 0.0434(4) Uani 1 1 d . . . . .
H13 H -0.2176 0.2901 -0.1615 0.052 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 C7 1.2124(16) . ?
N1 N2 1.3307(15) . ?
N1 C15 1.3302(16) . ?
C7 C6 1.4859(18) . ?
C7 C8 1.5311(18) . ?
N2 N3 1.3232(15) . ?
N2 C8 1.4453(16) . ?
C9 C15 1.4660(19) . ?
C9 C10 1.3937(18) . ?
C9 C14 1.3950(18) . ?
C6 C5 1.3914(18) . ?
C6 C1 1.3997(18) . ?
C15 N4 1.3559(16) . ?
N3 N4 1.3188(16) . ?
C5 H5 0.9300 . ?
C5 C4 1.3838(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 H1 0.9300 . ?
C1 C2 1.3806(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.381(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(2) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9300 . ?

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 N1 N2 101.58(10) . . ?
O1 C7 C6 122.71(12) . . ?
O1 C7 C8 119.23(12) . . ?
C6 C7 C8 118.07(11) . . ?
N1 N2 C8 122.68(11) . . ?
N3 N2 N1 114.18(11) . . ?
N3 N2 C8 122.61(11) . . ?
C10 C9 C15 120.38(12) . . ?
C10 C9 C14 119.25(13) . . ?
C14 C9 C15 120.37(12) . . ?
C5 C6 C7 122.52(11) . . ?
C5 C6 C1 119.38(12) . . ?
C1 C6 C7 118.08(12) . . ?
N1 C15 C9 123.59(11) . . ?
N1 C15 N4 112.06(12) . . ?
N4 C15 C9 124.35(11) . . ?
N4 N3 N2 105.79(10) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.37(12) . . ?
C4 C5 H5 119.8 . . ?
N3 N4 C15 106.39(11) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
N2 C8 C7 110.18(11) . . ?
N2 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.86(13) . . ?
C2 C1 H1 120.1 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.31(13) . . ?
C11 C10 H10 119.8 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.83(14) . . ?
C3 C4 H4 120.1 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.49(12) . . ?
C3 C2 H2 119.8 . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.68(13) . . ?
C13 C14 H14 120.2 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.24(14) . . ?
C12 C11 H11 119.9 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.04(13) . . ?
C2 C3 H3 120.0 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.71(14) . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.81(14) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?

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
O1 C7 C6 C5 -175.95(13) . . . . ?
O1 C7 C6 C1 2.16(19) . . . . ?
O1 C7 C8 N2 4.94(17) . . . . ?
N1 N2 N3 N4 0.92(15) . . . . ?
N1 N2 C8 C7 88.26(14) . . . . ?
N1 C15 N4 N3 -0.02(15) . . . . ?
C7 C6 C5 C4 176.49(12) . . . . ?
C7 C6 C1 C2 -177.28(12) . . . . ?
N2 N1 C15 C9 -179.01(11) . . . . ?
N2 N1 C15 N4 0.53(13) . . . . ?
N2 N3 N4 C15 -0.51(14) . . . . ?
C9 C15 N4 N3 179.52(11) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C9 C14 C13 C12 0.6(2) . . . . ?
C6 C7 C8 N2 -174.50(10) . . . . ?
C6 C5 C4 C3 0.7(2) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C15 N1 N2 N3 -0.90(13) . . . . ?
C15 N1 N2 C8 -172.66(11) . . . . ?
C15 C9 C10 C11 -178.81(12) . . . . ?
C15 C9 C14 C13 178.69(12) . . . . ?
N3 N2 C8 C7 -82.82(15) . . . . ?
C5 C6 C1 C2 0.89(19) . . . . ?
C5 C4 C3 C2 0.9(2) . . . . ?
C8 C7 C6 C5 3.46(18) . . . . ?
C8 C7 C6 C1 -178.43(11) . . . . ?
C8 N2 N3 N4 172.70(11) . . . . ?
C1 C6 C5 C4 -1.59(19) . . . . ?
C1 C2 C3 C4 -1.6(2) . . . . ?
C10 C9 C15 N1 -15.01(19) . . . . ?
C10 C9 C15 N4 165.51(12) . . . . ?
C10 C9 C14 C13 -0.8(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C14 C9 C15 N1 165.48(12) . . . . ?
C14 C9 C15 N4 -14.0(2) . . . . ?
C14 C9 C10 C11 0.71(19) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.771
