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

data_a201125a
_database_code_depnum_ccdc_archive 'CCDC 2072981'
loop_
_audit_author_name
_audit_author_address
'Pengchong Xue'
;Tianjin Normal University
China
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 N2, 2(C8 F4 N2)'
_chemical_formula_sum            'C44 H24 F8 N6'
_chemical_formula_weight         788.69
_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'
F F 0.0171 0.0103 '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'

_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                   7.1682(7)
_cell_length_b                   8.2406(9)
_cell_length_c                   29.792(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.704(8)
_cell_angle_gamma                90
_cell_volume                     1757.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2330
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3690
_cell_measurement_theta_min      2.5810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.001
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_min         2.565
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  20.00   1.00    1.53    --  -10.61 -99.00 -30.00   28
  2  ω      5.00  47.00   1.00    1.53    --   11.47 -99.00 -90.00   42
  3  ω    -67.00  51.00   1.00    1.53    --   11.47 -19.00   0.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0329695000
_diffrn_orient_matrix_UB_12      -0.0163836000
_diffrn_orient_matrix_UB_13      0.0216212000
_diffrn_orient_matrix_UB_21      0.0159962000
_diffrn_orient_matrix_UB_22      0.0820729000
_diffrn_orient_matrix_UB_23      0.0062450000
_diffrn_orient_matrix_UB_31      -0.0919926000
_diffrn_orient_matrix_UB_32      0.0201160000
_diffrn_orient_matrix_UB_33      -0.0078756000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                2363
_reflns_number_total             3093
_reflns_odcompleteness_completeness 99.95
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.259
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0106(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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.051
_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)+(0.0340P)²+0.2870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.1010
_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:
 C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N3 N 0.3343(2) 0.1899(2) 0.41561(5) 0.0254(4) Uani 1 1 d . . . . .
C9 C 0.2784(2) 0.3514(2) 0.41476(6) 0.0234(4) Uani 1 1 d . . . . .
C10 C 0.2252(2) 0.4497(2) 0.45000(7) 0.0277(5) Uani 1 1 d . . . . .
H10 H 0.2287 0.4121 0.4795 0.033 Uiso 1 1 calc R . . . .
C11 C 0.1669(2) 0.6060(3) 0.43932(7) 0.0307(5) Uani 1 1 d . . . . .
H11 H 0.1289 0.6741 0.4621 0.037 Uiso 1 1 calc R . . . .
C12 C 0.1638(2) 0.6636(3) 0.39525(7) 0.0293(5) Uani 1 1 d . . . . .
H12 H 0.1226 0.7687 0.3892 0.035 Uiso 1 1 calc R . . . .
C13 C 0.2207(2) 0.5674(2) 0.36046(7) 0.0263(5) Uani 1 1 d . . . . .
H13 H 0.2207 0.6076 0.3313 0.032 Uiso 1 1 calc R . . . .
C14 C 0.2784(2) 0.4085(2) 0.36986(6) 0.0222(5) Uani 1 1 d . . . . .
C15 C 0.3381(2) 0.2754(2) 0.34265(6) 0.0219(4) Uani 1 1 d . . . . .
C16 C 0.3713(2) 0.1430(2) 0.37212(6) 0.0236(5) Uani 1 1 d . . . . .
C17 C 0.4322(2) -0.0060(2) 0.35667(7) 0.0279(5) Uani 1 1 d . . . . .
H17 H 0.4552 -0.0924 0.3762 0.034 Uiso 1 1 calc R . . . .
C18 C 0.4576(2) -0.0213(3) 0.31114(7) 0.0313(5) Uani 1 1 d . . . . .
H18 H 0.4969 -0.1203 0.3000 0.038 Uiso 1 1 calc R . . . .
C19 C 0.4257(2) 0.1079(3) 0.28159(7) 0.0305(5) Uani 1 1 d . . . . .
H19 H 0.4454 0.0941 0.2512 0.037 Uiso 1 1 calc R . . . .
C20 C 0.3651(2) 0.2562(3) 0.29690(6) 0.0269(5) Uani 1 1 d . . . . .
H20 H 0.3428 0.3418 0.2770 0.032 Uiso 1 1 calc R . . . .
C21 C 0.3265(2) 0.0806(2) 0.45394(7) 0.0276(5) Uani 1 1 d . . . . .
H21A H 0.2874 -0.0256 0.4431 0.033 Uiso 1 1 calc R . . . .
H21B H 0.2318 0.1198 0.4735 0.033 Uiso 1 1 calc R . . . .
C22 C 0.5086(2) 0.0622(2) 0.48144(6) 0.0237(5) Uani 1 1 d . . . . .
H22A H 0.5440 0.1661 0.4945 0.028 Uiso 1 1 calc R . . . .
H22B H 0.6062 0.0289 0.4619 0.028 Uiso 1 1 calc R . . . .
F1 F 0.81058(15) 0.31716(14) 0.45392(4) 0.0341(3) Uani 1 1 d . . . . .
F2 F 0.91610(14) 0.04480(14) 0.41189(4) 0.0340(3) Uani 1 1 d . . . . .
F3 F 0.82926(16) 0.30763(16) 0.27225(4) 0.0415(4) Uani 1 1 d . . . . .
F4 F 0.71176(16) 0.57614(15) 0.31417(4) 0.0459(4) Uani 1 1 d . . . . .
N1 N 0.9802(2) -0.0922(2) 0.30281(7) 0.0416(5) Uani 1 1 d . . . . .
N2 N 0.6598(2) 0.7069(2) 0.42817(7) 0.0443(5) Uani 1 1 d . . . . .
C1 C 0.8117(2) 0.3137(2) 0.40907(6) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.8670(2) 0.1760(2) 0.38751(7) 0.0244(5) Uani 1 1 d . . . . .
C3 C 0.8738(2) 0.1705(2) 0.34118(7) 0.0258(5) Uani 1 1 d . . . . .
C4 C 0.8213(2) 0.3089(3) 0.31683(6) 0.0284(5) Uani 1 1 d . . . . .
C5 C 0.7634(3) 0.4460(3) 0.33833(7) 0.0291(5) Uani 1 1 d . . . . .
C6 C 0.7583(2) 0.4516(2) 0.38483(7) 0.0271(5) Uani 1 1 d . . . . .
C7 C 0.9324(3) 0.0254(3) 0.31920(7) 0.0308(5) Uani 1 1 d . . . . .
C8 C 0.7020(3) 0.5951(3) 0.40823(7) 0.0320(5) 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
N3 C9 1.390(2) . ?
N3 C16 1.390(2) . ?
N3 C21 1.458(2) . ?
C9 C10 1.393(3) . ?
C9 C14 1.418(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(3) . ?
C14 C15 1.441(3) . ?
C15 C16 1.414(3) . ?
C15 C20 1.395(3) . ?
C16 C17 1.388(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.393(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.516(2) . ?
C22 C22 1.517(4) 3_656 ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
F1 C1 1.337(2) . ?
F2 C2 1.340(2) . ?
F3 C4 1.332(2) . ?
F4 C5 1.334(2) . ?
N1 C7 1.145(3) . ?
N2 C8 1.145(3) . ?
C1 C2 1.371(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.394(3) . ?
C3 C7 1.435(3) . ?
C4 C5 1.372(3) . ?
C5 C6 1.388(3) . ?
C6 C8 1.440(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
C9 N3 C21 125.76(16) . . ?
C16 N3 C9 108.49(15) . . ?
C16 N3 C21 125.05(17) . . ?
N3 C9 C10 129.19(18) . . ?
N3 C9 C14 108.77(17) . . ?
C10 C9 C14 122.03(18) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.22(18) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.5(2) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.22(19) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.85(19) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C15 106.97(17) . . ?
C13 C14 C9 119.12(18) . . ?
C13 C14 C15 133.89(18) . . ?
C16 C15 C14 106.49(16) . . ?
C20 C15 C14 134.01(18) . . ?
C20 C15 C16 119.50(18) . . ?
N3 C16 C15 109.27(17) . . ?
C17 C16 N3 129.20(18) . . ?
C17 C16 C15 121.53(18) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 C16 117.63(19) . . ?
C18 C17 H17 121.2 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 H20 120.6 . . ?
C19 C20 C15 118.87(19) . . ?
C19 C20 H20 120.6 . . ?
N3 C21 H21A 108.5 . . ?
N3 C21 H21B 108.5 . . ?
N3 C21 C22 114.92(15) . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C21 C22 C22 111.37(18) . 3_656 ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C22 C22 H22A 109.4 3_656 . ?
C22 C22 H22B 109.4 3_656 . ?
H22A C22 H22B 108.0 . . ?
F1 C1 C2 120.10(18) . . ?
F1 C1 C6 119.14(18) . . ?
C2 C1 C6 120.75(18) . . ?
F2 C2 C1 119.20(18) . . ?
F2 C2 C3 119.55(18) . . ?
C1 C2 C3 121.25(18) . . ?
C2 C3 C4 118.08(19) . . ?
C2 C3 C7 120.47(19) . . ?
C4 C3 C7 121.45(19) . . ?
F3 C4 C3 119.27(19) . . ?
F3 C4 C5 120.02(19) . . ?
C5 C4 C3 120.71(19) . . ?
F4 C5 C4 119.47(19) . . ?
F4 C5 C6 119.46(19) . . ?
C4 C5 C6 121.06(19) . . ?
C1 C6 C8 119.75(19) . . ?
C5 C6 C1 118.14(19) . . ?
C5 C6 C8 122.11(19) . . ?
N1 C7 C3 178.1(2) . . ?
N2 C8 C6 177.6(2) . . ?

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
N3 C9 C10 C11 -177.00(16) . . . . ?
N3 C9 C14 C13 177.93(15) . . . . ?
N3 C9 C14 C15 -0.34(19) . . . . ?
N3 C16 C17 C18 179.63(16) . . . . ?
N3 C21 C22 C22 -176.1(2) . . . 3_656 ?
C9 N3 C16 C15 -0.31(19) . . . . ?
C9 N3 C16 C17 179.39(17) . . . . ?
C9 N3 C21 C22 -97.8(2) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C9 C14 C15 C16 0.15(18) . . . . ?
C9 C14 C15 C20 179.84(18) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C10 C9 C14 C15 -179.23(15) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C12 C13 C14 C9 -0.6(2) . . . . ?
C12 C13 C14 C15 177.14(17) . . . . ?
C13 C14 C15 C16 -177.75(18) . . . . ?
C13 C14 C15 C20 1.9(3) . . . . ?
C14 C9 C10 C11 1.6(3) . . . . ?
C14 C15 C16 N3 0.09(18) . . . . ?
C14 C15 C16 C17 -179.64(15) . . . . ?
C14 C15 C20 C19 179.77(17) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 N3 C9 C10 179.19(17) . . . . ?
C16 N3 C9 C14 0.41(19) . . . . ?
C16 N3 C21 C22 92.8(2) . . . . ?
C16 C15 C20 C19 -0.6(2) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C15 0.6(3) . . . . ?
C20 C15 C16 N3 -179.65(15) . . . . ?
C20 C15 C16 C17 0.6(2) . . . . ?
C21 N3 C9 C10 8.4(3) . . . . ?
C21 N3 C9 C14 -170.43(15) . . . . ?
C21 N3 C16 C15 170.61(15) . . . . ?
C21 N3 C16 C17 -9.7(3) . . . . ?
F1 C1 C2 F2 1.3(2) . . . . ?
F1 C1 C2 C3 -178.39(16) . . . . ?
F1 C1 C6 C5 178.99(16) . . . . ?
F1 C1 C6 C8 -0.3(3) . . . . ?
F2 C2 C3 C4 179.79(15) . . . . ?
F2 C2 C3 C7 0.2(3) . . . . ?
F3 C4 C5 F4 1.4(3) . . . . ?
F3 C4 C5 C6 -178.40(16) . . . . ?
F4 C5 C6 C1 179.59(16) . . . . ?
F4 C5 C6 C8 -1.1(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C7 179.90(16) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C8 -179.57(16) . . . . ?
C2 C3 C4 F3 179.00(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 F4 -179.23(16) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C8 178.62(17) . . . . ?
C6 C1 C2 F2 -179.44(15) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C3 C4 F3 -1.4(3) . . . . ?
C7 C3 C4 C5 179.16(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-25
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.837

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/n-hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_n201222a
_database_code_depnum_ccdc_archive 'CCDC 2073042'
loop_
_audit_author_name
_audit_author_address
'Pengchong Xue'
;Tianjin Normal University
China
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 N5'
_chemical_formula_weight         372.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.694(5)
_cell_length_b                   7.226(2)
_cell_length_c                   17.313(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.538(7)
_cell_angle_gamma                90
_cell_volume                     1954.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1617
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      21.74

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   0.983
_exptl_transmission_factor_max   0.986
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12318
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.304
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4041
_reflns_number_gt                2458
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0647P)²+0.0140P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4041
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
N1 N 0.35717(10) 0.1680(2) 0.43431(9) 0.0431(4) Uani 1 1 d . . . . .
N2 N 0.42750(13) 0.5941(3) 0.32972(13) 0.0735(6) Uani 1 1 d . . . . .
N3 N 0.34553(13) 0.7015(3) 0.53810(11) 0.0682(6) Uani 1 1 d . . . . .
N4 N -0.05657(13) 0.4089(3) 0.40105(12) 0.0769(6) Uani 1 1 d . . . . .
N5 N 0.01686(14) 0.3286(3) 0.19761(12) 0.0797(7) Uani 1 1 d . . . . .
C1 C 0.33998(12) 0.1007(2) 0.35920(11) 0.0417(5) Uani 1 1 d . . . . .
C2 C 0.39301(14) 0.0885(3) 0.29961(12) 0.0544(6) Uani 1 1 d . . . . .
H2 H 0.4497 0.1272 0.3067 0.065 Uiso 1 1 calc R U . . .
C3 C 0.35882(15) 0.0173(3) 0.22997(12) 0.0628(6) Uani 1 1 d . . . . .
H3 H 0.3935 0.0060 0.1896 0.075 Uiso 1 1 calc R U . . .
C4 C 0.27364(16) -0.0385(3) 0.21814(12) 0.0627(6) Uani 1 1 d . . . . .
H4 H 0.2523 -0.0851 0.1700 0.075 Uiso 1 1 calc R U . . .
C5 C 0.22078(14) -0.0257(3) 0.27652(12) 0.0520(6) Uani 1 1 d . . . . .
H5 H 0.1639 -0.0627 0.2682 0.062 Uiso 1 1 calc R U . . .
C6 C 0.25353(12) 0.0437(2) 0.34859(11) 0.0405(5) Uani 1 1 d . . . . .
C7 C 0.21781(12) 0.0769(2) 0.42071(11) 0.0402(5) Uani 1 1 d . . . . .
C8 C 0.13696(13) 0.0525(3) 0.44580(13) 0.0516(5) Uani 1 1 d . . . . .
H8 H 0.0928 0.0007 0.4131 0.062 Uiso 1 1 calc R U . . .
C9 C 0.12334(15) 0.1066(3) 0.52010(13) 0.0617(6) Uani 1 1 d . . . . .
H9 H 0.0696 0.0909 0.5376 0.074 Uiso 1 1 calc R U . . .
C10 C 0.18938(15) 0.1844(3) 0.56916(12) 0.0592(6) Uani 1 1 d . . . . .
H10 H 0.1784 0.2223 0.6186 0.071 Uiso 1 1 calc R U . . .
C11 C 0.27028(14) 0.2068(3) 0.54656(11) 0.0499(5) Uani 1 1 d . . . . .
H11 H 0.3144 0.2558 0.5801 0.060 Uiso 1 1 calc R U . . .
C12 C 0.28362(12) 0.1534(2) 0.47178(11) 0.0398(5) Uani 1 1 d . . . . .
C13 C 0.44000(12) 0.2294(3) 0.47135(11) 0.0485(5) Uani 1 1 d . . . . .
H13A H 0.4316 0.3383 0.5025 0.058 Uiso 1 1 calc R U . . .
H13B H 0.4764 0.2643 0.4315 0.058 Uiso 1 1 calc R U . . .
C14 C 0.48492(12) 0.0810(2) 0.52273(11) 0.0455(5) Uani 1 1 d . . . . .
H14A H 0.5338 0.1358 0.5529 0.055 Uiso 1 1 calc R U . . .
H14B H 0.4459 0.0363 0.5587 0.055 Uiso 1 1 calc R U . . .
C15 C 0.35725(14) 0.5772(3) 0.33905(12) 0.0507(5) Uani 1 1 d . . . . .
C16 C 0.26862(12) 0.5509(2) 0.35146(11) 0.0424(5) Uani 1 1 d . . . . .
C17 C 0.24049(12) 0.5883(2) 0.42387(11) 0.0415(5) Uani 1 1 d . . . . .
C18 C 0.15600(13) 0.5574(3) 0.43717(11) 0.0452(5) Uani 1 1 d . . . . .
H18 H 0.1376 0.5830 0.4855 0.054 Uiso 1 1 calc R U . . .
C19 C 0.09934(12) 0.4883(3) 0.37812(11) 0.0428(5) Uani 1 1 d . . . . .
C20 C 0.12682(12) 0.4533(3) 0.30499(11) 0.0439(5) Uani 1 1 d . . . . .
C21 C 0.21137(13) 0.4841(3) 0.29199(12) 0.0469(5) Uani 1 1 d . . . . .
H21 H 0.2297 0.4601 0.2435 0.056 Uiso 1 1 calc R U . . .
C22 C 0.29912(14) 0.6544(3) 0.48715(12) 0.0501(5) Uani 1 1 d . . . . .
C23 C 0.01230(14) 0.4463(3) 0.39151(12) 0.0540(6) Uani 1 1 d . . . . .
C24 C 0.06660(14) 0.3831(3) 0.24429(13) 0.0549(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
N1 C12 1.382(2) . ?
N1 C1 1.390(2) . ?
N1 C13 1.462(2) . ?
N2 C15 1.136(3) . ?
N3 C22 1.140(2) . ?
N4 C23 1.142(3) . ?
N5 C24 1.138(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.413(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.437(3) . ?
C7 C8 1.391(3) . ?
C7 C12 1.406(3) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.522(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C14 1.512(4) 3_656 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.440(3) . ?
C16 C21 1.386(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.386(3) . ?
C17 C22 1.442(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.400(3) . ?
C19 C23 1.440(3) . ?
C20 C21 1.385(3) . ?
C20 C24 1.436(3) . ?
C21 H21 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
C12 N1 C1 108.47(15) . . ?
C12 N1 C13 124.41(16) . . ?
C1 N1 C13 126.91(17) . . ?
C2 C1 N1 129.84(19) . . ?
C2 C1 C6 121.43(18) . . ?
N1 C1 C6 108.71(17) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.14(19) . . ?
C5 C6 C7 134.07(19) . . ?
C1 C6 C7 106.78(16) . . ?
C8 C7 C12 119.34(18) . . ?
C8 C7 C6 133.94(18) . . ?
C12 C7 C6 106.70(16) . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.42(19) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
N1 C12 C11 128.72(18) . . ?
N1 C12 C7 109.34(16) . . ?
C11 C12 C7 121.91(18) . . ?
N1 C13 C14 112.62(16) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C14 C14 C13 113.1(2) 3_656 . ?
C14 C14 H14A 109.0 3_656 . ?
C13 C14 H14A 109.0 . . ?
C14 C14 H14B 109.0 3_656 . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N2 C15 C16 178.5(2) . . ?
C21 C16 C17 119.75(18) . . ?
C21 C16 C15 120.08(19) . . ?
C17 C16 C15 120.15(18) . . ?
C18 C17 C16 120.59(18) . . ?
C18 C17 C22 118.54(18) . . ?
C16 C17 C22 120.84(18) . . ?
C19 C18 C17 119.54(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.15(18) . . ?
C18 C19 C23 120.64(18) . . ?
C20 C19 C23 119.18(18) . . ?
C21 C20 C19 120.10(18) . . ?
C21 C20 C24 120.73(18) . . ?
C19 C20 C24 119.16(18) . . ?
C20 C21 C16 119.85(19) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
N3 C22 C17 178.0(2) . . ?
N4 C23 C19 178.2(3) . . ?
N5 C24 C20 177.9(2) . . ?

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
C12 N1 C1 C2 179.27(18) . . . . ?
C13 N1 C1 C2 -5.8(3) . . . . ?
C12 N1 C1 C6 0.57(19) . . . . ?
C13 N1 C1 C6 175.51(16) . . . . ?
N1 C1 C2 C3 -179.20(18) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C5 178.63(16) . . . . ?
C2 C1 C6 C7 -179.39(17) . . . . ?
N1 C1 C6 C7 -0.56(19) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C1 C6 C7 C8 178.9(2) . . . . ?
C5 C6 C7 C12 -178.7(2) . . . . ?
C1 C6 C7 C12 0.34(19) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -177.6(2) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
C1 N1 C12 C11 -178.51(18) . . . . ?
C13 N1 C12 C11 6.4(3) . . . . ?
C1 N1 C12 C7 -0.3(2) . . . . ?
C13 N1 C12 C7 -175.45(16) . . . . ?
C10 C11 C12 N1 177.18(18) . . . . ?
C10 C11 C12 C7 -0.8(3) . . . . ?
C8 C7 C12 N1 -178.81(16) . . . . ?
C6 C7 C12 N1 0.0(2) . . . . ?
C8 C7 C12 C11 -0.5(3) . . . . ?
C6 C7 C12 C11 178.31(17) . . . . ?
C12 N1 C13 C14 75.9(2) . . . . ?
C1 N1 C13 C14 -98.2(2) . . . . ?
N1 C13 C14 C14 69.0(3) . . . 3_656 ?
C21 C16 C17 C18 0.7(3) . . . . ?
C15 C16 C17 C18 -177.76(17) . . . . ?
C21 C16 C17 C22 178.75(17) . . . . ?
C15 C16 C17 C22 0.3(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C22 C17 C18 C19 -177.88(17) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C17 C18 C19 C23 176.91(18) . . . . ?
C18 C19 C20 C21 1.3(3) . . . . ?
C23 C19 C20 C21 -176.83(18) . . . . ?
C18 C19 C20 C24 -179.43(18) . . . . ?
C23 C19 C20 C24 2.4(3) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C24 C20 C21 C16 -179.63(18) . . . . ?
C17 C16 C21 C20 -0.6(3) . . . . ?
C15 C16 C21 C20 177.86(18) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/n-haxane'
_exptl_crystal_preparation       Luminescent
