# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2048684'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Ma'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_audit_creation_date             2020-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 N3'
_chemical_formula_sum            'C18 H11 N3'
_chemical_formula_weight         269.30
_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'

_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                   9.0032(3)
_cell_length_b                   7.3984(2)
_cell_length_c                   20.0691(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.3690(10)
_cell_angle_gamma                90
_cell_volume                     1336.76(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            61043
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         2.474
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2449
_reflns_number_total             2946
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.222
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0118(16)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.065
_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)+(0.0355P)²+0.3953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C9(H9), C5(H5), C14(H14), C10(H10), C16(H16), C0AA(H0AA),
 C3(H3), C4(H4), C15(H15)
;
_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
N3 N 0.69325(12) 0.67408(15) 0.29334(5) 0.0414(3) Uani 1 1 d . . . . .
N2 N 0.88326(12) 0.62384(14) 0.21756(5) 0.0431(3) Uani 1 1 d . . . . .
C12 C 0.67974(14) 0.70016(17) 0.40661(6) 0.0411(3) Uani 1 1 d . . . . .
C7 C 0.77487(14) 0.71444(16) 0.35136(6) 0.0397(3) Uani 1 1 d . . . . .
C6 C 0.74573(15) 0.68373(17) 0.22745(6) 0.0413(3) Uani 1 1 d . . . . .
C17 C 0.54720(14) 0.62946(17) 0.31221(7) 0.0417(3) Uani 1 1 d . . . . .
C13 C 0.53663(15) 0.64254(17) 0.38166(7) 0.0424(3) Uani 1 1 d . . . . .
C2 C 0.93331(16) 0.63077(18) 0.15457(7) 0.0469(3) Uani 1 1 d . . . . .
C8 C 0.92251(15) 0.76550(19) 0.35900(7) 0.0471(3) Uani 1 1 d . . . . .
H8 H 0.9872 0.7724 0.3219 0.056 Uiso 1 1 calc R . . . .
C11 C 0.73306(17) 0.7420(2) 0.46998(7) 0.0499(3) Uani 1 1 d . . . . .
H11 H 0.6697 0.7336 0.5075 0.060 Uiso 1 1 calc R . . . .
N1 N 1.20580(18) 0.5348(2) 0.13422(8) 0.0778(5) Uani 1 1 d . . . . .
C9 C 0.97184(17) 0.8059(2) 0.42267(8) 0.0546(4) Uani 1 1 d . . . . .
H9 H 1.0722 0.8418 0.4291 0.066 Uiso 1 1 calc R . . . .
C1 C 1.08582(19) 0.5738(2) 0.14461(7) 0.0559(4) Uani 1 1 d . . . . .
C5 C 0.65658(17) 0.7556(2) 0.17709(7) 0.0508(3) Uani 1 1 d . . . . .
H5 H 0.5613 0.8039 0.1867 0.061 Uiso 1 1 calc R . . . .
C14 C 0.40453(16) 0.5954(2) 0.41325(8) 0.0517(4) Uani 1 1 d . . . . .
H14 H 0.3963 0.6033 0.4603 0.062 Uiso 1 1 calc R . . . .
C10 C 0.87840(17) 0.7955(2) 0.47767(7) 0.0559(4) Uani 1 1 d . . . . .
H10 H 0.9154 0.8255 0.5207 0.067 Uiso 1 1 calc R . . . .
C16 C 0.42744(16) 0.5714(2) 0.27358(8) 0.0515(4) Uani 1 1 d . . . . .
H16 H 0.4344 0.5630 0.2265 0.062 Uiso 1 1 calc R . . . .
C0AA C 0.28654(17) 0.5374(2) 0.37517(8) 0.0597(4) Uani 1 1 d . . . . .
H0AA H 0.1962 0.5045 0.3961 0.072 Uiso 1 1 calc R . . . .
C3 C 0.85052(19) 0.6887(2) 0.10102(7) 0.0572(4) Uani 1 1 d . . . . .
H3 H 0.8889 0.6834 0.0571 0.069 Uiso 1 1 calc R . . . .
C4 C 0.71003(19) 0.7548(2) 0.11295(7) 0.0587(4) Uani 1 1 d . . . . .
H4 H 0.6507 0.7994 0.0773 0.070 Uiso 1 1 calc R . . . .
C15 C 0.29800(17) 0.5262(2) 0.30629(9) 0.0603(4) Uani 1 1 d . . . . .
H15 H 0.2146 0.4865 0.2810 0.072 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C7 1.4050(16) . ?
N3 C6 1.4088(16) . ?
N3 C17 1.4099(16) . ?
N2 C6 1.3312(17) . ?
N2 C2 1.3458(16) . ?
C12 C7 1.4094(17) . ?
C12 C13 1.4437(19) . ?
C12 C11 1.3912(19) . ?
C7 C8 1.3894(19) . ?
C6 C5 1.3920(19) . ?
C17 C13 1.4010(18) . ?
C17 C16 1.3920(19) . ?
C13 C14 1.3956(19) . ?
C2 C1 1.451(2) . ?
C2 C3 1.373(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.375(2) . ?
N1 C1 1.139(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(2) . ?
C14 H14 0.9500 . ?
C14 C0AA 1.373(2) . ?
C10 H10 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.382(2) . ?
C0AA H0AA 0.9500 . ?
C0AA C15 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(2) . ?
C4 H4 0.9500 . ?
C15 H15 0.9500 . ?

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
C7 N3 C6 126.18(11) . . ?
C7 N3 C17 108.11(10) . . ?
C6 N3 C17 125.66(11) . . ?
C6 N2 C2 116.41(12) . . ?
C7 C12 C13 107.14(11) . . ?
C11 C12 C7 119.65(12) . . ?
C11 C12 C13 133.21(12) . . ?
N3 C7 C12 108.60(11) . . ?
C8 C7 N3 130.10(12) . . ?
C8 C7 C12 121.28(12) . . ?
N2 C6 N3 116.17(11) . . ?
N2 C6 C5 123.46(12) . . ?
C5 C6 N3 120.36(12) . . ?
C13 C17 N3 108.70(11) . . ?
C16 C17 N3 130.03(12) . . ?
C16 C17 C13 121.20(12) . . ?
C17 C13 C12 107.41(11) . . ?
C14 C13 C12 132.65(13) . . ?
C14 C13 C17 119.88(13) . . ?
N2 C2 C1 116.17(13) . . ?
N2 C2 C3 124.33(14) . . ?
C3 C2 C1 119.50(13) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 C7 117.53(13) . . ?
C9 C8 H8 121.2 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.28(13) . . ?
C10 C11 H11 120.4 . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.85(14) . . ?
C10 C9 H9 119.1 . . ?
N1 C1 C2 176.63(18) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.28(14) . . ?
C4 C5 H5 120.9 . . ?
C13 C14 H14 120.5 . . ?
C0AA C14 C13 118.93(14) . . ?
C0AA C14 H14 120.5 . . ?
C11 C10 C9 120.39(14) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C17 C16 H16 121.2 . . ?
C15 C16 C17 117.56(14) . . ?
C15 C16 H16 121.2 . . ?
C14 C0AA H0AA 119.7 . . ?
C14 C0AA C15 120.67(14) . . ?
C15 C0AA H0AA 119.7 . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 117.97(14) . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 119.37(14) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C16 C15 C0AA 121.76(15) . . ?
C16 C15 H15 119.1 . . ?
C0AA C15 H15 119.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ma1
_database_code_depnum_ccdc_archive 'CCDC 2048685'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Ma'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 N3'
_chemical_formula_weight         269.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   9.0308(3)
_cell_length_b                   7.5081(2)
_cell_length_c                   20.1212(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9470(10)
_cell_angle_gamma                90.00
_cell_volume                     1347.70(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.918
_cell_measurement_theta_max      28.363

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            54900
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         26.73
_reflns_number_total             2866
_reflns_number_gt                2306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.3116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2862
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.85649(11) 0.51305(15) 0.23931(6) 0.0417(3) Uani 1 1 d . . .
N2 N 0.90592(13) 0.60482(17) 0.35032(6) 0.0508(3) Uani 1 1 d . . .
C3 C 1.00337(13) 0.46004(16) 0.23176(7) 0.0400(3) Uani 1 1 d . . .
C4 C 1.01461(15) 0.46110(18) 0.16338(7) 0.0440(3) Uani 1 1 d . . .
C5 C 0.80567(14) 0.53791(17) 0.30109(7) 0.0411(3) Uani 1 1 d . . .
C6 C 0.66060(15) 0.49075(19) 0.30979(7) 0.0476(3) Uani 1 1 d . . .
H1 H 0.5921 0.4436 0.2734 0.057 Uiso 1 1 calc R . .
C7 C 1.12120(15) 0.40344(19) 0.27990(7) 0.0464(3) Uani 1 1 d . . .
H2 H 1.1136 0.4039 0.3265 0.056 Uiso 1 1 calc R . .
C8 C 0.77608(14) 0.54630(17) 0.17510(7) 0.0415(3) Uani 1 1 d . . .
C9 C 0.72275(17) 0.5811(2) 0.42383(8) 0.0545(4) Uani 1 1 d . . .
C10 C 0.87150(15) 0.51866(18) 0.12735(7) 0.0452(3) Uani 1 1 d . . .
C11 C 0.61873(16) 0.5138(2) 0.37182(8) 0.0538(4) Uani 1 1 d . . .
H3 H 0.5202 0.4842 0.3791 0.065 Uiso 1 1 calc R . .
C12 C 0.86409(18) 0.6233(2) 0.41044(8) 0.0573(4) Uani 1 1 d . . .
H4 H 0.9355 0.6680 0.4462 0.069 Uiso 1 1 calc R . .
C13 C 1.26383(17) 0.3468(2) 0.18957(9) 0.0602(4) Uani 1 1 d . . .
H5 H 1.3542 0.3068 0.1758 0.072 Uiso 1 1 calc R . .
C14 C 1.25001(16) 0.3463(2) 0.25710(8) 0.0540(4) Uani 1 1 d . . .
H6 H 1.3318 0.3054 0.2889 0.065 Uiso 1 1 calc R . .
C15 C 0.82014(19) 0.5509(2) 0.05991(8) 0.0603(4) Uani 1 1 d . . .
H7 H 0.8844 0.5334 0.0273 0.072 Uiso 1 1 calc R . .
C16 C 1.14733(17) 0.4048(2) 0.14236(8) 0.0572(4) Uani 1 1 d . . .
H8 H 1.1569 0.4067 0.0960 0.069 Uiso 1 1 calc R . .
C17 C 0.6752(2) 0.6086(3) 0.04054(8) 0.0674(5) Uani 1 1 d . . .
H9 H 0.6389 0.6301 -0.0057 0.081 Uiso 1 1 calc R . .
C18 C 0.62980(15) 0.60614(19) 0.15584(8) 0.0502(3) Uani 1 1 d . . .
H10 H 0.5652 0.6260 0.1881 0.060 Uiso 1 1 calc R . .
C1 C 0.58180(18) 0.6356(2) 0.08828(8) 0.0620(4) Uani 1 1 d . . .
H11 H 0.4821 0.6755 0.0740 0.074 Uiso 1 1 calc R . .
C2 C 0.6895(2) 0.6061(3) 0.49075(9) 0.0735(5) Uani 1 1 d . . .
N3 N 0.6668(2) 0.6279(3) 0.54432(9) 0.1077(7) 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 C8 1.4026(17) . ?
N1 C5 1.4030(16) . ?
N1 C3 1.4155(15) . ?
N2 C12 1.3293(19) . ?
N2 C5 1.3320(18) . ?
C3 C7 1.3894(19) . ?
C3 C4 1.3954(19) . ?
C4 C16 1.3970(19) . ?
C4 C10 1.4461(19) . ?
C5 C6 1.3941(18) . ?
C6 C11 1.370(2) . ?
C7 C14 1.3832(19) . ?
C8 C18 1.3920(19) . ?
C8 C10 1.4022(18) . ?
C9 C12 1.382(2) . ?
C9 C11 1.388(2) . ?
C9 C2 1.437(2) . ?
C10 C15 1.385(2) . ?
C13 C16 1.374(2) . ?
C13 C14 1.384(2) . ?
C15 C17 1.376(2) . ?
C17 C1 1.388(2) . ?
C18 C1 1.379(2) . ?
C2 N3 1.140(2) . ?

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
C8 N1 C5 126.78(11) . . ?
C8 N1 C3 108.11(10) . . ?
C5 N1 C3 125.00(11) . . ?
C12 N2 C5 117.36(12) . . ?
C7 C3 C4 121.60(12) . . ?
C7 C3 N1 129.79(12) . . ?
C4 C3 N1 108.50(11) . . ?
C3 C4 C16 119.61(13) . . ?
C3 C4 C10 107.43(11) . . ?
C16 C4 C10 132.90(13) . . ?
N2 C5 C6 123.08(13) . . ?
N2 C5 N1 115.53(11) . . ?
C6 C5 N1 121.38(13) . . ?
C11 C6 C5 118.69(14) . . ?
C14 C7 C3 117.13(14) . . ?
C18 C8 C10 120.98(13) . . ?
C18 C8 N1 130.30(13) . . ?
C10 C8 N1 108.63(11) . . ?
C12 C9 C11 118.28(13) . . ?
C12 C9 C2 119.14(15) . . ?
C11 C9 C2 122.57(14) . . ?
C15 C10 C8 119.83(13) . . ?
C15 C10 C4 132.86(13) . . ?
C8 C10 C4 107.30(12) . . ?
C6 C11 C9 118.84(13) . . ?
N2 C12 C9 123.73(14) . . ?
C16 C13 C14 120.22(13) . . ?
C7 C14 C13 122.26(14) . . ?
C17 C15 C10 119.41(15) . . ?
C13 C16 C4 119.17(14) . . ?
C15 C17 C1 120.23(15) . . ?
C1 C18 C8 117.74(14) . . ?
C18 C1 C17 121.80(15) . . ?
N3 C2 C9 178.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2048686'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Ma'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_audit_creation_date             2019-11-12
_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         'C18 H11 N3'
_chemical_formula_sum            'C18 H11 N3'
_chemical_formula_weight         269.30
_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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.664(3)
_cell_length_b                   11.881(2)
_cell_length_c                   15.315(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2668.2(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8098
_cell_measurement_temperature    162(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.3887
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17004
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.001
_diffrn_ambient_temperature      162.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2307
_reflns_number_total             2343
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.288
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.288
_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)+(0.0290P)²+1.5136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1174
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
;
_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
N1 N 0.20483(11) 0.41364(13) 0.10217(10) 0.0283(4) Uani 1 1 d . . . . .
N2 N 0.32466(11) 0.34734(14) 0.18733(11) 0.0313(4) Uani 1 1 d . . . . .
C3 C 0.24228(13) 0.32719(16) 0.15404(12) 0.0254(4) Uani 1 1 d . . . . .
C4 C 0.11244(14) 0.55801(16) 0.05857(13) 0.0313(5) Uani 1 1 d . . . . .
C5 C 0.10780(15) 0.20357(16) 0.12930(14) 0.0318(5) Uani 1 1 d . . . . .
C6 C 0.19496(13) 0.22640(16) 0.16879(12) 0.0273(4) Uani 1 1 d . . . . .
C7 C 0.23465(14) 0.14592(17) 0.22299(13) 0.0318(5) Uani 1 1 d . . . . .
H7 H 0.204021 0.077174 0.234964 0.038 Uiso 1 1 calc R . . . .
C8 C 0.33771(15) 0.45387(18) 0.00125(13) 0.0354(5) Uani 1 1 d . . . . .
H8 H 0.374938 0.393710 0.021218 0.042 Uiso 1 1 calc R . . . .
N9 N 0.03700(13) 0.18347(16) 0.10080(13) 0.0433(5) Uani 1 1 d . . . . .
C10 C 0.31889(14) 0.16751(17) 0.25892(13) 0.0330(5) Uani 1 1 d . . . . .
H10 H 0.346951 0.114913 0.297144 0.040 Uiso 1 1 calc R . . . .
C11 C 0.19507(15) 0.56126(16) 0.00739(13) 0.0322(5) Uani 1 1 d . . . . .
C12 C 0.12087(13) 0.46774(16) 0.11726(13) 0.0283(4) Uani 1 1 d . . . . .
C13 C 0.25183(14) 0.47321(16) 0.03654(12) 0.0293(5) Uani 1 1 d . . . . .
C14 C 0.36155(14) 0.26740(17) 0.23803(14) 0.0342(5) Uani 1 1 d . . . . .
H14 H 0.420797 0.280380 0.261011 0.041 Uiso 1 1 calc R . . . .
C15 C 0.03409(16) 0.62521(18) 0.06144(15) 0.0417(6) Uani 1 1 d . . . . .
H15 H 0.026327 0.685649 0.021519 0.050 Uiso 1 1 calc R . . . .
C16 C 0.36683(17) 0.52582(19) -0.06418(14) 0.0428(6) Uani 1 1 d . . . . .
H16 H 0.425392 0.515287 -0.089426 0.051 Uiso 1 1 calc R . . . .
C17 C 0.05585(14) 0.44637(17) 0.18125(14) 0.0342(5) Uani 1 1 d . . . . .
H17 H 0.063614 0.387175 0.222279 0.041 Uiso 1 1 calc R . . . .
C18 C -0.02075(15) 0.51476(18) 0.18287(17) 0.0426(6) Uani 1 1 d . . . . .
H18 H -0.066611 0.501675 0.225492 0.051 Uiso 1 1 calc R . . . .
C19 C 0.22609(18) 0.63247(18) -0.05871(14) 0.0425(6) Uani 1 1 d . . . . .
H19 H 0.189069 0.692599 -0.079090 0.051 Uiso 1 1 calc R . . . .
C20 C -0.03178(16) 0.60201(19) 0.12344(17) 0.0470(6) Uani 1 1 d . . . . .
H20 H -0.085550 0.646531 0.125430 0.056 Uiso 1 1 calc R . . . .
C21 C 0.31110(19) 0.6143(2) -0.09387(14) 0.0482(6) Uani 1 1 d . . . . .
H21 H 0.332571 0.662250 -0.139016 0.058 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.410(2) . ?
N1 C12 1.408(2) . ?
N1 C13 1.409(2) . ?
N2 C3 1.333(2) . ?
N2 C14 1.341(3) . ?
C3 C6 1.402(3) . ?
C4 C11 1.444(3) . ?
C4 C12 1.405(3) . ?
C4 C15 1.400(3) . ?
C5 C6 1.440(3) . ?
C5 N9 1.151(3) . ?
C6 C7 1.394(3) . ?
C7 H7 0.9500 . ?
C7 C10 1.376(3) . ?
C8 H8 0.9500 . ?
C8 C13 1.390(3) . ?
C8 C16 1.385(3) . ?
C10 H10 0.9500 . ?
C10 C14 1.379(3) . ?
C11 C13 1.409(3) . ?
C11 C19 1.396(3) . ?
C12 C17 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C20 1.382(3) . ?
C16 H16 0.9500 . ?
C16 C21 1.407(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C18 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C21 1.375(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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 C3 125.50(16) . . ?
C12 N1 C13 108.39(16) . . ?
C13 N1 C3 125.26(16) . . ?
C3 N2 C14 117.38(17) . . ?
N2 C3 N1 115.96(17) . . ?
N2 C3 C6 122.71(18) . . ?
C6 C3 N1 121.33(17) . . ?
C12 C4 C11 107.10(17) . . ?
C15 C4 C11 133.7(2) . . ?
C15 C4 C12 119.2(2) . . ?
N9 C5 C6 177.3(2) . . ?
C3 C6 C5 122.18(18) . . ?
C7 C6 C3 118.36(18) . . ?
C7 C6 C5 119.45(18) . . ?
C6 C7 H7 120.5 . . ?
C10 C7 C6 119.02(19) . . ?
C10 C7 H7 120.5 . . ?
C13 C8 H8 121.3 . . ?
C16 C8 H8 121.3 . . ?
C16 C8 C13 117.3(2) . . ?
C7 C10 H10 120.8 . . ?
C7 C10 C14 118.34(19) . . ?
C14 C10 H10 120.8 . . ?
C13 C11 C4 107.69(17) . . ?
C19 C11 C4 133.1(2) . . ?
C19 C11 C13 119.2(2) . . ?
C4 C12 N1 108.68(17) . . ?
C17 C12 N1 129.19(18) . . ?
C17 C12 C4 122.00(19) . . ?
N1 C13 C11 108.05(18) . . ?
C8 C13 N1 129.61(18) . . ?
C8 C13 C11 122.32(19) . . ?
N2 C14 C10 124.12(19) . . ?
N2 C14 H14 117.9 . . ?
C10 C14 H14 117.9 . . ?
C4 C15 H15 120.6 . . ?
C20 C15 C4 118.8(2) . . ?
C20 C15 H15 120.6 . . ?
C8 C16 H16 119.5 . . ?
C8 C16 C21 121.0(2) . . ?
C21 C16 H16 119.5 . . ?
C12 C17 H17 121.3 . . ?
C18 C17 C12 117.5(2) . . ?
C18 C17 H17 121.3 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C20 121.3(2) . . ?
C20 C18 H18 119.3 . . ?
C11 C19 H19 120.5 . . ?
C21 C19 C11 119.0(2) . . ?
C21 C19 H19 120.5 . . ?
C15 C20 C18 121.2(2) . . ?
C15 C20 H20 119.4 . . ?
C18 C20 H20 119.4 . . ?
C16 C21 H21 119.4 . . ?
C19 C21 C16 121.2(2) . . ?
C19 C21 H21 119.4 . . ?

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
N1 C3 C6 C5 2.6(3) . . . . ?
N1 C3 C6 C7 -177.97(17) . . . . ?
N1 C12 C17 C18 178.44(19) . . . . ?
N2 C3 C6 C5 -177.17(18) . . . . ?
N2 C3 C6 C7 2.3(3) . . . . ?
C3 N1 C12 C4 172.70(17) . . . . ?
C3 N1 C12 C17 -3.3(3) . . . . ?
C3 N1 C13 C8 8.4(3) . . . . ?
C3 N1 C13 C11 -172.89(17) . . . . ?
C3 N2 C14 C10 -1.3(3) . . . . ?
C3 C6 C7 C10 -0.9(3) . . . . ?
C4 C11 C13 N1 2.0(2) . . . . ?
C4 C11 C13 C8 -179.13(18) . . . . ?
C4 C11 C19 C21 178.5(2) . . . . ?
C4 C12 C17 C18 2.9(3) . . . . ?
C4 C15 C20 C18 0.8(3) . . . . ?
C5 C6 C7 C10 178.60(18) . . . . ?
C6 C7 C10 C14 -1.4(3) . . . . ?
C7 C10 C14 N2 2.7(3) . . . . ?
C8 C16 C21 C19 0.3(3) . . . . ?
C11 C4 C12 N1 -1.6(2) . . . . ?
C11 C4 C12 C17 174.77(18) . . . . ?
C11 C4 C15 C20 -176.1(2) . . . . ?
C11 C19 C21 C16 -0.2(3) . . . . ?
C12 N1 C3 N2 -122.5(2) . . . . ?
C12 N1 C3 C6 57.7(3) . . . . ?
C12 N1 C13 C8 178.3(2) . . . . ?
C12 N1 C13 C11 -3.0(2) . . . . ?
C12 C4 C11 C13 -0.3(2) . . . . ?
C12 C4 C11 C19 -178.5(2) . . . . ?
C12 C4 C15 C20 1.4(3) . . . . ?
C12 C17 C18 C20 -0.6(3) . . . . ?
C13 N1 C3 N2 45.6(3) . . . . ?
C13 N1 C3 C6 -134.1(2) . . . . ?
C13 N1 C12 C4 2.9(2) . . . . ?
C13 N1 C12 C17 -173.14(19) . . . . ?
C13 C8 C16 C21 -0.5(3) . . . . ?
C13 C11 C19 C21 0.4(3) . . . . ?
C14 N2 C3 N1 179.04(17) . . . . ?
C14 N2 C3 C6 -1.2(3) . . . . ?
C15 C4 C11 C13 177.4(2) . . . . ?
C15 C4 C11 C19 -0.8(4) . . . . ?
C15 C4 C12 N1 -179.69(17) . . . . ?
C15 C4 C12 C17 -3.3(3) . . . . ?
C16 C8 C13 N1 179.19(19) . . . . ?
C16 C8 C13 C11 0.6(3) . . . . ?
C17 C18 C20 C15 -1.2(4) . . . . ?
C19 C11 C13 N1 -179.42(17) . . . . ?
C19 C11 C13 C8 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
