# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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 1899181'
loop_
_audit_author_name
_audit_author_address
'He Zhao'
;South China University of Technology
China
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2020-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 N3'
_chemical_formula_sum            'C33 H25 N3'
_chemical_formula_weight         463.56

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                   10.7120(10)
_cell_length_b                   26.2639(17)
_cell_length_c                   9.6385(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.352(11)
_cell_angle_gamma                90
_cell_volume                     2470.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5748
_cell_measurement_theta_min      3.740
_cell_measurement_theta_max      29.441

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17981
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.740
_diffrn_reflns_theta_max         29.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5748
_reflns_number_gt                3890
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.7742P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5748
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.40785(15) 0.25069(5) 0.75545(18) 0.0429(4) Uani 1 1 d . . . . .
N2 N 0.21768(14) 0.22174(5) 0.50713(17) 0.0427(4) Uani 1 1 d . . . . .
N3 N 0.20492(16) 0.02493(5) 0.28577(17) 0.0444(4) Uani 1 1 d . . . . .
C1 C 0.33365(17) 0.21765(7) 0.6407(2) 0.0391(4) Uani 1 1 d . . . . .
C2 C 0.38305(17) 0.16849(6) 0.6689(2) 0.0372(4) Uani 1 1 d . . . . .
C3 C 0.49940(17) 0.16968(7) 0.81448(19) 0.0376(4) Uani 1 1 d . . . . .
C4 C 0.59192(18) 0.13400(7) 0.9099(2) 0.0443(4) Uani 1 1 d . . . . .
H4A H 0.5876 0.1001 0.8800 0.053 Uiso 1 1 calc R U . . .
C5 C 0.6902(2) 0.14967(9) 1.0496(2) 0.0561(5) Uani 1 1 d . . . . .
H5A H 0.7513 0.1259 1.1136 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6994(2) 0.20015(9) 1.0959(2) 0.0612(6) Uani 1 1 d . . . . .
H6A H 0.7662 0.2095 1.1904 0.073 Uiso 1 1 calc R U . . .
C7 C 0.6112(2) 0.23655(8) 1.0042(2) 0.0546(5) Uani 1 1 d . . . . .
H7A H 0.6183 0.2704 1.0350 0.066 Uiso 1 1 calc R U . . .
C8 C 0.51132(17) 0.22127(7) 0.8643(2) 0.0414(4) Uani 1 1 d . . . . .
C9 C 0.4012(2) 0.30579(7) 0.7575(3) 0.0564(6) Uani 1 1 d . . . . .
H9A H 0.4659 0.3182 0.8540 0.085 Uiso 1 1 calc R U . . .
H9B H 0.4229 0.3195 0.6776 0.085 Uiso 1 1 calc R U . . .
H9C H 0.3105 0.3162 0.7421 0.085 Uiso 1 1 calc R U . . .
C10 C 0.13056(18) 0.26477(7) 0.4443(2) 0.0419(4) Uani 1 1 d . . . . .
C11 C 0.0010(2) 0.26485(9) 0.4407(3) 0.0587(6) Uani 1 1 d . . . . .
H11A H -0.0295 0.2376 0.4800 0.070 Uiso 1 1 calc R U . . .
C12 C -0.0839(3) 0.30675(12) 0.3766(3) 0.0818(9) Uani 1 1 d . . . . .
H12A H -0.1727 0.3071 0.3711 0.098 Uiso 1 1 calc R U . . .
C13 C -0.0373(4) 0.34705(12) 0.3222(3) 0.0953(11) Uani 1 1 d . . . . .
H13A H -0.0937 0.3751 0.2821 0.114 Uiso 1 1 calc R U . . .
C14 C 0.0907(4) 0.34648(10) 0.3261(3) 0.0892(9) Uani 1 1 d . . . . .
H14A H 0.1214 0.3740 0.2879 0.107 Uiso 1 1 calc R U . . .
C15 C 0.1757(3) 0.30514(9) 0.3868(3) 0.0641(6) Uani 1 1 d . . . . .
H15A H 0.2632 0.3047 0.3886 0.077 Uiso 1 1 calc R U . . .
C16 C 0.19230(17) 0.17258(6) 0.4440(2) 0.0382(4) Uani 1 1 d . . . . .
C17 C 0.29372(16) 0.13828(6) 0.54174(19) 0.0357(4) Uani 1 1 d . . . . .
C18 C 0.29373(17) 0.08843(7) 0.4917(2) 0.0380(4) Uani 1 1 d . . . . .
H18A H 0.3574 0.0650 0.5537 0.046 Uiso 1 1 calc R U . . .
C19 C 0.19792(18) 0.07390(6) 0.3483(2) 0.0396(4) Uani 1 1 d . . . . .
C20 C 0.09858(19) 0.10830(7) 0.2564(2) 0.0448(4) Uani 1 1 d . . . . .
H20A H 0.0339 0.0976 0.1622 0.054 Uiso 1 1 calc R U . . .
C21 C 0.09455(18) 0.15775(7) 0.3026(2) 0.0445(5) Uani 1 1 d . . . . .
H21A H 0.0283 0.1805 0.2410 0.053 Uiso 1 1 calc R U . . .
C22 C 0.24109(19) 0.02425(7) 0.1593(2) 0.0426(4) Uani 1 1 d . . . . .
C23 C 0.1774(2) -0.00945(8) 0.0409(2) 0.0555(5) Uani 1 1 d . . . . .
H23A H 0.1127 -0.0322 0.0455 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2090(3) -0.00962(11) -0.0834(3) 0.0778(8) Uani 1 1 d . . . . .
H24A H 0.1654 -0.0325 -0.1624 0.093 Uiso 1 1 calc R U . . .
C25 C 0.3028(4) 0.02318(13) -0.0920(4) 0.1039(11) Uani 1 1 d . . . . .
H25A H 0.3232 0.0232 -0.1769 0.125 Uiso 1 1 calc R U . . .
C26 C 0.3675(4) 0.05638(13) 0.0254(5) 0.1226(14) Uani 1 1 d . . . . .
H26A H 0.4330 0.0787 0.0204 0.147 Uiso 1 1 calc R U . . .
C27 C 0.3369(3) 0.05725(10) 0.1510(3) 0.0832(8) Uani 1 1 d . . . . .
H27A H 0.3811 0.0801 0.2298 0.100 Uiso 1 1 calc R U . . .
C28 C 0.22532(19) -0.01927(7) 0.3758(2) 0.0416(4) Uani 1 1 d . . . . .
C29 C 0.1427(3) -0.02891(8) 0.4507(3) 0.0635(6) Uani 1 1 d . . . . .
H29A H 0.0747 -0.0058 0.4437 0.076 Uiso 1 1 calc R U . . .
C30 C 0.1600(3) -0.07288(10) 0.5364(3) 0.0767(8) Uani 1 1 d . . . . .
H30A H 0.1037 -0.0791 0.5867 0.092 Uiso 1 1 calc R U . . .
C31 C 0.2604(3) -0.10738(9) 0.5473(3) 0.0764(8) Uani 1 1 d . . . . .
H31A H 0.2724 -0.1368 0.6050 0.092 Uiso 1 1 calc R U . . .
C32 C 0.3418(3) -0.09799(10) 0.4730(3) 0.0743(7) Uani 1 1 d . . . . .
H32A H 0.4093 -0.1213 0.4797 0.089 Uiso 1 1 calc R U . . .
C33 C 0.3256(2) -0.05462(8) 0.3883(3) 0.0573(5) Uani 1 1 d . . . . .
H33A H 0.3825 -0.0488 0.3387 0.069 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
N1 C1 1.372(2) . ?
N1 C8 1.403(2) . ?
N1 C9 1.449(2) . ?
N2 C1 1.376(2) . ?
N2 C16 1.405(2) . ?
N2 C10 1.431(2) . ?
N3 C28 1.411(2) . ?
N3 C22 1.423(2) . ?
N3 C19 1.435(2) . ?
C1 C2 1.379(2) . ?
C2 C3 1.443(2) . ?
C2 C17 1.442(2) . ?
C3 C4 1.398(2) . ?
C3 C8 1.426(2) . ?
C4 C5 1.386(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.378(3) . ?
C7 C8 1.391(3) . ?
C10 C15 1.373(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.399(3) . ?
C12 C13 1.365(4) . ?
C13 C14 1.355(4) . ?
C14 C15 1.382(3) . ?
C16 C21 1.389(2) . ?
C16 C17 1.427(2) . ?
C17 C18 1.395(2) . ?
C18 C19 1.392(2) . ?
C19 C20 1.399(3) . ?
C20 C21 1.380(2) . ?
C22 C27 1.371(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.373(3) . ?
C24 C25 1.352(4) . ?
C25 C26 1.369(5) . ?
C26 C27 1.378(4) . ?
C28 C29 1.377(3) . ?
C28 C33 1.387(3) . ?
C29 C30 1.387(3) . ?
C30 C31 1.377(4) . ?
C31 C32 1.360(4) . ?
C32 C33 1.370(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
C1 N1 C8 105.72(14) . . ?
C1 N1 C9 128.83(16) . . ?
C8 N1 C9 124.61(15) . . ?
C1 N2 C16 105.80(13) . . ?
C1 N2 C10 129.56(14) . . ?
C16 N2 C10 124.50(14) . . ?
C28 N3 C22 119.23(14) . . ?
C28 N3 C19 120.03(14) . . ?
C22 N3 C19 116.79(14) . . ?
C2 C1 N1 112.68(15) . . ?
C2 C1 N2 112.47(15) . . ?
N1 C1 N2 134.77(16) . . ?
C1 C2 C3 106.18(15) . . ?
C1 C2 C17 106.35(15) . . ?
C3 C2 C17 147.43(16) . . ?
C4 C3 C8 118.33(16) . . ?
C4 C3 C2 136.00(16) . . ?
C8 C3 C2 105.64(15) . . ?
C5 C4 C3 119.25(18) . . ?
C4 C5 C6 121.32(19) . . ?
C5 C6 C7 121.16(18) . . ?
C8 C7 C6 118.12(19) . . ?
C7 C8 N1 128.39(17) . . ?
C7 C8 C3 121.81(17) . . ?
N1 C8 C3 109.77(14) . . ?
C15 C10 C11 120.57(19) . . ?
C15 C10 N2 120.25(18) . . ?
C11 C10 N2 119.17(19) . . ?
C10 C11 C12 118.6(2) . . ?
C13 C12 C11 120.3(3) . . ?
C14 C13 C12 120.5(2) . . ?
C15 C14 C13 120.2(3) . . ?
C14 C15 C10 119.8(2) . . ?
C21 C16 C17 122.13(16) . . ?
C21 C16 N2 127.98(16) . . ?
C17 C16 N2 109.61(14) . . ?
C18 C17 C16 118.21(15) . . ?
C18 C17 C2 135.68(16) . . ?
C16 C17 C2 105.75(14) . . ?
C19 C18 C17 119.69(16) . . ?
C18 C19 C20 120.56(16) . . ?
C18 C19 N3 121.17(16) . . ?
C20 C19 N3 118.09(15) . . ?
C21 C20 C19 121.38(16) . . ?
C20 C21 C16 118.00(17) . . ?
C27 C22 C23 118.9(2) . . ?
C27 C22 N3 121.13(18) . . ?
C23 C22 N3 119.96(17) . . ?
C24 C23 C22 120.5(2) . . ?
C23 C24 C25 120.5(3) . . ?
C26 C25 C24 119.4(3) . . ?
C25 C26 C27 120.9(3) . . ?
C22 C27 C26 119.7(3) . . ?
C29 C28 C33 118.27(19) . . ?
C29 C28 N3 120.24(17) . . ?
C33 C28 N3 121.47(18) . . ?
C30 C29 C28 120.6(2) . . ?
C29 C30 C31 120.1(2) . . ?
C32 C31 C30 119.4(2) . . ?
C31 C32 C33 120.9(2) . . ?
C32 C33 C28 120.8(2) . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041

