# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1988014'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Ma'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-03-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_audit_creation_date             2019-09-24
_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         'C23 H15 N3'
_chemical_formula_sum            'C23 H15 N3'
_chemical_formula_weight         333.38
_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 0.0033 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/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                   8.4001(4)
_cell_length_b                   27.6987(14)
_cell_length_c                   7.4900(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.621(2)
_cell_angle_gamma                90
_cell_volume                     1718.20(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8556
_cell_measurement_temperature    283(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_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            ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             696
_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  0.0543
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27768
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.942
_diffrn_ambient_temperature      283.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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                2657
_reflns_number_total             3947
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.215
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.030(4)
_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     237
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0500
_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)+(0.0664P)²+0.4994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C002(H002), C003(H003), C004(H004), C007(H007), C00B(H00B), C00G(H00G),
 C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00C,H00D)
;
_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
N001 N 0.38525(16) 0.58643(5) 0.2469(2) 0.0462(4) Uani 1 1 d . . . . .
C002 C 0.3651(2) 0.49990(6) 0.2967(2) 0.0454(4) Uani 1 1 d . . . . .
H002 H 0.2635 0.5043 0.3280 0.054 Uiso 1 1 calc R . . . .
C003 C 0.4294(2) 0.45429(7) 0.2958(2) 0.0469(4) Uani 1 1 d . . . . .
H003 H 0.3676 0.4280 0.3200 0.056 Uiso 1 1 calc R . . . .
C004 C 0.6722(2) 0.48683(6) 0.2187(2) 0.0469(4) Uani 1 1 d . . . . .
H004 H 0.7773 0.4829 0.1970 0.056 Uiso 1 1 calc R . . . .
C005 C 0.5856(2) 0.44642(6) 0.2594(2) 0.0451(4) Uani 1 1 d . . . . .
C006 C 0.4518(2) 0.53958(6) 0.2509(2) 0.0436(4) Uani 1 1 d . . . . .
C007 C 0.6056(2) 0.53225(7) 0.2099(2) 0.0467(4) Uani 1 1 d . . . . .
H007 H 0.6637 0.5583 0.1763 0.056 Uiso 1 1 calc R . . . .
C008 C 0.4667(2) 0.62917(6) 0.3091(2) 0.0470(4) Uani 1 1 d . . . . .
C009 C 0.2227(2) 0.59832(7) 0.1835(2) 0.0473(4) Uani 1 1 d . . . . .
N00A N 1.0361(2) 0.44352(7) 0.4616(3) 0.0801(6) Uani 1 1 d . . . . .
C00B C 0.0967(2) 0.56944(8) 0.0981(3) 0.0533(5) Uani 1 1 d . . . . .
H00B H 0.1108 0.5366 0.0812 0.064 Uiso 1 1 calc R . . . .
C00C C 0.6508(2) 0.39709(6) 0.2616(2) 0.0473(4) Uani 1 1 d . . . . .
C00D C 0.2009(2) 0.64786(7) 0.2085(3) 0.0524(5) Uani 1 1 d . . . . .
C00E C 0.8075(2) 0.38614(7) 0.3243(3) 0.0509(4) Uani 1 1 d . . . . .
C00F C 0.9307(2) 0.41949(7) 0.4013(3) 0.0568(5) Uani 1 1 d . . . . .
C00G C 0.6286(2) 0.63697(7) 0.3828(3) 0.0553(5) Uani 1 1 d . . . . .
H00G H 0.7029 0.6118 0.3959 0.066 Uiso 1 1 calc R . . . .
C00H C 0.3555(2) 0.66746(7) 0.2900(3) 0.0527(5) Uani 1 1 d . . . . .
C00I C -0.0500(2) 0.59171(9) 0.0396(3) 0.0628(6) Uani 1 1 d . . . . .
H00I H -0.1355 0.5734 -0.0199 0.075 Uiso 1 1 calc R . . . .
C00J C 0.8654(3) 0.33741(8) 0.3217(3) 0.0624(5) Uani 1 1 d . . . . .
C00K C 0.5375(2) 0.35728(7) 0.1889(3) 0.0612(5) Uani 1 1 d . . . . .
H00A H 0.4674 0.3501 0.2743 0.092 Uiso 1 1 calc GR . . . .
H00C H 0.5985 0.3290 0.1697 0.092 Uiso 1 1 calc GR . . . .
H00D H 0.4742 0.3672 0.0762 0.092 Uiso 1 1 calc GR . . . .
N00L N 0.9132(3) 0.29877(7) 0.3227(4) 0.0894(7) Uani 1 1 d . . . . .
C00M C 0.6744(3) 0.68330(8) 0.4354(3) 0.0678(6) Uani 1 1 d . . . . .
H00M H 0.7818 0.6893 0.4839 0.081 Uiso 1 1 calc R . . . .
C00N C -0.0732(3) 0.64035(9) 0.0670(3) 0.0734(7) Uani 1 1 d . . . . .
H00N H -0.1742 0.6540 0.0278 0.088 Uiso 1 1 calc R . . . .
C00O C 0.0510(3) 0.66894(9) 0.1515(3) 0.0687(6) Uani 1 1 d . . . . .
H00O H 0.0349 0.7017 0.1701 0.082 Uiso 1 1 calc R . . . .
C00P C 0.4055(3) 0.71362(8) 0.3461(4) 0.0710(6) Uani 1 1 d . . . . .
H00P H 0.3320 0.7390 0.3349 0.085 Uiso 1 1 calc R . . . .
C00Q C 0.5649(3) 0.72132(8) 0.4183(4) 0.0780(7) Uani 1 1 d . . . . .
H00Q H 0.5997 0.7521 0.4559 0.094 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
N001 C006 1.411(2) . ?
N001 C008 1.407(2) . ?
N001 C009 1.408(2) . ?
C002 C003 1.374(2) . ?
C002 C006 1.393(2) . ?
C003 C005 1.401(3) . ?
C004 C005 1.396(2) . ?
C004 C007 1.374(2) . ?
C005 C00C 1.471(2) . ?
C006 C007 1.392(2) . ?
C008 C00G 1.397(3) . ?
C008 C00H 1.405(3) . ?
C009 C00B 1.394(2) . ?
C009 C00D 1.401(3) . ?
N00A C00F 1.140(2) . ?
C00B C00I 1.382(3) . ?
C00C C00E 1.356(2) . ?
C00C C00K 1.498(2) . ?
C00D C00H 1.445(3) . ?
C00D C00O 1.389(3) . ?
C00E C00F 1.434(3) . ?
C00E C00J 1.436(3) . ?
C00G C00M 1.378(3) . ?
C00H C00P 1.389(3) . ?
C00I C00N 1.382(3) . ?
C00J N00L 1.143(3) . ?
C00M C00Q 1.390(3) . ?
C00N C00O 1.377(3) . ?
C00P C00Q 1.375(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
C008 N001 C006 126.71(14) . . ?
C008 N001 C009 107.79(14) . . ?
C009 N001 C006 125.48(14) . . ?
C003 C002 C006 120.18(16) . . ?
C002 C003 C005 121.68(16) . . ?
C007 C004 C005 121.42(17) . . ?
C003 C005 C00C 120.11(16) . . ?
C004 C005 C003 117.20(16) . . ?
C004 C005 C00C 122.68(16) . . ?
C002 C006 N001 120.64(15) . . ?
C007 C006 N001 120.56(16) . . ?
C007 C006 C002 118.80(16) . . ?
C004 C007 C006 120.58(16) . . ?
C00G C008 N001 130.43(17) . . ?
C00G C008 C00H 120.71(17) . . ?
C00H C008 N001 108.85(15) . . ?
C00B C009 N001 129.78(18) . . ?
C00B C009 C00D 121.16(17) . . ?
C00D C009 N001 108.96(15) . . ?
C00I C00B C009 117.2(2) . . ?
C005 C00C C00K 117.83(16) . . ?
C00E C00C C005 123.35(16) . . ?
C00E C00C C00K 118.82(17) . . ?
C009 C00D C00H 107.22(16) . . ?
C00O C00D C009 120.18(18) . . ?
C00O C00D C00H 132.6(2) . . ?
C00C C00E C00F 126.05(18) . . ?
C00C C00E C00J 121.10(17) . . ?
C00F C00E C00J 112.84(17) . . ?
N00A C00F C00E 175.2(2) . . ?
C00M C00G C008 117.62(19) . . ?
C008 C00H C00D 107.15(16) . . ?
C00P C00H C008 120.12(18) . . ?
C00P C00H C00D 132.73(19) . . ?
C00N C00I C00B 121.93(19) . . ?
N00L C00J C00E 178.7(2) . . ?
C00G C00M C00Q 122.1(2) . . ?
C00O C00N C00I 120.9(2) . . ?
C00N C00O C00D 118.5(2) . . ?
C00Q C00P C00H 119.2(2) . . ?
C00P C00Q C00M 120.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
