# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2102218'
loop_
_audit_author_name
_audit_author_address
'fengcheng jia'
;wuhan institute of technology
China
;
_audit_update_record             
;
2021-08-08 deposited with the CCDC.	2021-10-04 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         ?
_chemical_formula_sum            'C15 H11 N'
_chemical_formula_weight         205.25

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   17.526
_cell_length_b                   22.025
_cell_length_c                   5.561
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2146.7
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3108
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      18.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56737
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_av_R_equivalents  0.1516
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.485
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3779
_reflns_number_gt                1899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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)+(0.1165P)²+1.2183P] 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_abs_structure_details 
;
 Flack x determined using 572 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3779
_refine_ls_number_parameters     241
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.2063
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2158
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.5533(3) 0.8421(3) 0.5478(10) 0.078(3) Uani 1 1 d DG . . . .
C2 C 0.5443(4) 0.9046(3) 0.5261(12) 0.091(3) Uani 1 1 d G . . . .
H2 H 0.5694 0.9255 0.4044 0.109 Uiso 1 1 calc R U . . .
C3 C 0.4978(4) 0.93577(19) 0.6865(15) 0.092(3) Uani 1 1 d G . . . .
H3 H 0.4918 0.9776 0.6719 0.111 Uiso 1 1 calc R U . . .
C4 C 0.4602(4) 0.9045(3) 0.8685(13) 0.092(3) Uani 1 1 d G . . . .
H4 H 0.4291 0.9254 0.9757 0.111 Uiso 1 1 calc R U . . .
C5 C 0.4692(3) 0.8420(3) 0.8902(10) 0.075(3) Uani 1 1 d G . . . .
H5 H 0.4441 0.8211 1.0120 0.090 Uiso 1 1 calc R U . . .
C6 C 0.5157(3) 0.81085(19) 0.7299(11) 0.063(2) Uani 1 1 d DG . . . .
C7 C 0.5357(4) 0.74785(16) 0.7034(15) 0.065(2) Uani 1 1 d D . . . .
C8 C 0.5832(5) 0.7444(4) 0.5124(19) 0.075(3) Uani 1 1 d D . . . .
N1 N 0.6057(5) 0.6835(4) 0.4597(16) 0.098(3) Uani 1 1 d D . . . .
H1 H 0.6355 0.6707 0.3478 0.118 Uiso 1 1 calc R U . . .
C10 C 0.5664(3) 0.6491(3) 0.6384(8) 0.074(3) Uani 1 1 d DG . . . .
C11 C 0.5235(3) 0.68677(19) 0.7865(9) 0.060(2) Uani 1 1 d DG . . . .
C12 C 0.4797(3) 0.6620(3) 0.9703(10) 0.082(3) Uani 1 1 d G . . . .
H12 H 0.4510 0.6872 1.0693 0.099 Uiso 1 1 calc R U . . .
C13 C 0.4788(4) 0.5995(3) 1.0061(13) 0.100(3) Uani 1 1 d G . . . .
H13 H 0.4495 0.5830 1.1291 0.120 Uiso 1 1 calc R U . . .
C14 C 0.5218(4) 0.5619(2) 0.8581(15) 0.099(3) Uani 1 1 d G . . . .
H14 H 0.5212 0.5201 0.8821 0.119 Uiso 1 1 calc R U . . .
C15 C 0.5655(4) 0.5866(3) 0.6743(12) 0.088(3) Uani 1 1 d G . . . .
H15 H 0.5943 0.5614 0.5752 0.106 Uiso 1 1 calc R U . . .
C16 C 0.3195(3) 0.7780(3) 0.3507(10) 0.063(2) Uani 1 1 d DG . . . .
C17 C 0.3226(3) 0.8411(3) 0.3478(12) 0.078(3) Uani 1 1 d G . . . .
H17 H 0.3515 0.8617 0.4620 0.094 Uiso 1 1 calc R U . . .
C18 C 0.2825(4) 0.87343(17) 0.1741(14) 0.083(3) Uani 1 1 d G . . . .
H18 H 0.2846 0.9156 0.1722 0.100 Uiso 1 1 calc R U . . .
C19 C 0.2394(3) 0.8427(3) 0.0034(12) 0.081(3) Uani 1 1 d G . . . .
H19 H 0.2126 0.8643 -0.1128 0.098 Uiso 1 1 calc R U . . .
C20 C 0.2362(3) 0.7796(3) 0.0063(10) 0.072(3) Uani 1 1 d G . . . .
H20 H 0.2074 0.7591 -0.1080 0.087 Uiso 1 1 calc R U . . .
C21 C 0.2763(3) 0.74732(17) 0.1799(11) 0.058(2) Uani 1 1 d DG . . . .
C22 C 0.2829(4) 0.68370(15) 0.2344(13) 0.058(2) Uani 1 1 d D . . . .
C23 C 0.3291(5) 0.6796(3) 0.4305(17) 0.066(3) Uani 1 1 d D . . . .
C24 C 0.3409(5) 0.6172(3) 0.5203(17) 0.067(2) Uani 1 1 d D . . . .
H24A H 0.3230 0.6124 0.6843 0.081 Uiso 1 1 calc R U . . .
H24B H 0.3940 0.6049 0.5100 0.081 Uiso 1 1 calc R U . . .
C25 C 0.2920(3) 0.5836(3) 0.3456(10) 0.070(2) Uani 1 1 d DG . . . .
C26 C 0.2584(3) 0.62284(19) 0.1808(11) 0.063(2) Uani 1 1 d DG . . . .
C27 C 0.2090(3) 0.6002(3) 0.0069(11) 0.080(3) Uani 1 1 d G . . . .
H27 H 0.1866 0.6265 -0.1033 0.096 Uiso 1 1 calc R U . . .
C28 C 0.1933(3) 0.5384(3) -0.0023(13) 0.095(3) Uani 1 1 d G . . . .
H28 H 0.1603 0.5233 -0.1187 0.114 Uiso 1 1 calc R U . . .
C29 C 0.2269(4) 0.4992(2) 0.1624(16) 0.102(4) Uani 1 1 d G . . . .
H29 H 0.2164 0.4579 0.1563 0.122 Uiso 1 1 calc R U . . .
C30 C 0.2763(4) 0.5218(3) 0.3364(13) 0.095(3) Uani 1 1 d G . . . .
H30 H 0.2988 0.4956 0.4466 0.114 Uiso 1 1 calc R U . . .
C9 C 0.5996(5) 0.8023(3) 0.4000(19) 0.073(3) Uani 1 1 d D . . . .
H9A H 0.5836 0.8031 0.2330 0.088 Uiso 1 1 calc R U . . .
H9B H 0.6534 0.8125 0.4104 0.088 Uiso 1 1 calc R U . . .
N2 N 0.3542(4) 0.7370(3) 0.5075(15) 0.075(2) Uani 1 1 d D . . . .
H2A H 0.3842 0.7451 0.6254 0.089 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C9 1.451(8) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.438(3) . ?
C7 C8 1.352(12) . ?
C7 C11 1.438(3) . ?
C8 C9 1.450(9) . ?
C8 N1 1.429(9) . ?
N1 C10 1.426(8) . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C16 N2 1.395(7) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.438(3) . ?
C22 C23 1.362(11) . ?
C22 C26 1.438(3) . ?
C23 N2 1.404(8) . ?
C23 C24 1.478(9) . ?
C24 C25 1.492(8) . ?
C25 C26 1.3900 . ?
C25 C30 1.3900 . ?
C26 C27 1.3900 . ?
C27 C28 1.3900 . ?
C28 C29 1.3900 . ?
C29 C30 1.3900 . ?

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
C2 C1 C6 120.0 . . ?
C2 C1 C9 127.8(6) . . ?
C6 C1 C9 112.2(6) . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 133.2(5) . . ?
C1 C6 C7 106.8(5) . . ?
C8 C7 C11 106.9(6) . . ?
C8 C7 C6 106.5(6) . . ?
C11 C7 C6 146.4(7) . . ?
C7 C8 C9 114.3(7) . . ?
C7 C8 N1 112.6(7) . . ?
C9 C8 N1 133.1(8) . . ?
C10 N1 C8 102.9(7) . . ?
C11 C10 C15 120.0 . . ?
C11 C10 N1 110.9(5) . . ?
C15 C10 N1 129.1(5) . . ?
C10 C11 C12 120.0 . . ?
C10 C11 C7 106.7(5) . . ?
C12 C11 C7 133.3(5) . . ?
C13 C12 C11 120.0 . . ?
C12 C13 C14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C14 C15 C10 120.0 . . ?
N2 C16 C17 129.6(5) . . ?
N2 C16 C21 110.4(5) . . ?
C17 C16 C21 120.0 . . ?
C16 C17 C18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C19 C20 C21 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 C22 133.3(5) . . ?
C16 C21 C22 106.7(5) . . ?
C23 C22 C21 106.3(5) . . ?
C23 C22 C26 106.4(5) . . ?
C21 C22 C26 147.2(7) . . ?
C22 C23 N2 111.8(6) . . ?
C22 C23 C24 114.5(6) . . ?
N2 C23 C24 133.7(8) . . ?
C23 C24 C25 99.3(6) . . ?
C26 C25 C30 120.0 . . ?
C26 C25 C24 111.4(5) . . ?
C30 C25 C24 128.6(5) . . ?
C27 C26 C25 120.0 . . ?
C27 C26 C22 131.6(5) . . ?
C25 C26 C22 108.4(5) . . ?
C26 C27 C28 120.0 . . ?
C27 C28 C29 120.0 . . ?
C30 C29 C28 120.0 . . ?
C29 C30 C25 120.0 . . ?
C8 C9 C1 100.1(7) . . ?
C16 N2 C23 104.8(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0 . . . . ?
C9 C1 C2 C3 -179.4(7) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 -179.3(8) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C9 C1 C6 C5 179.5(6) . . . . ?
C2 C1 C6 C7 179.4(6) . . . . ?
C9 C1 C6 C7 -1.1(7) . . . . ?
C5 C6 C7 C8 179.5(6) . . . . ?
C1 C6 C7 C8 0.2(7) . . . . ?
C5 C6 C7 C11 4.4(18) . . . . ?
C1 C6 C7 C11 -174.9(12) . . . . ?
C11 C7 C8 C9 178.0(8) . . . . ?
C6 C7 C8 C9 0.8(10) . . . . ?
C11 C7 C8 N1 -0.8(10) . . . . ?
C6 C7 C8 N1 -178.0(8) . . . . ?
C7 C8 N1 C10 0.4(10) . . . . ?
C9 C8 N1 C10 -178.1(9) . . . . ?
C8 N1 C10 C11 0.1(8) . . . . ?
C8 N1 C10 C15 178.9(6) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
N1 C10 C11 C12 178.9(6) . . . . ?
C15 C10 C11 C7 -179.5(6) . . . . ?
N1 C10 C11 C7 -0.6(7) . . . . ?
C8 C7 C11 C10 0.9(7) . . . . ?
C6 C7 C11 C10 175.9(12) . . . . ?
C8 C7 C11 C12 -178.5(6) . . . . ?
C6 C7 C11 C12 -3.5(18) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C7 C11 C12 C13 179.3(8) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
N1 C10 C15 C14 -178.6(7) . . . . ?
N2 C16 C17 C18 -179.4(7) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C19 C20 C21 C22 177.9(7) . . . . ?
N2 C16 C21 C20 179.5(5) . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
N2 C16 C21 C22 1.1(6) . . . . ?
C17 C16 C21 C22 -178.4(5) . . . . ?
C20 C21 C22 C23 -178.5(5) . . . . ?
C16 C21 C22 C23 -0.4(7) . . . . ?
C20 C21 C22 C26 -4.2(16) . . . . ?
C16 C21 C22 C26 173.9(11) . . . . ?
C21 C22 C23 N2 -0.5(8) . . . . ?
C26 C22 C23 N2 -177.3(6) . . . . ?
C21 C22 C23 C24 178.0(7) . . . . ?
C26 C22 C23 C24 1.2(9) . . . . ?
C22 C23 C24 C25 -1.0(9) . . . . ?
N2 C23 C24 C25 177.2(9) . . . . ?
C23 C24 C25 C26 0.3(7) . . . . ?
C23 C24 C25 C30 -177.7(5) . . . . ?
C30 C25 C26 C27 0.0 . . . . ?
C24 C25 C26 C27 -178.3(6) . . . . ?
C30 C25 C26 C22 178.6(6) . . . . ?
C24 C25 C26 C22 0.3(6) . . . . ?
C23 C22 C26 C27 177.5(5) . . . . ?
C21 C22 C26 C27 3.2(15) . . . . ?
C23 C22 C26 C25 -0.9(7) . . . . ?
C21 C22 C26 C25 -175.2(11) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C22 C26 C27 C28 -178.2(7) . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C29 C30 C25 0.0 . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
C24 C25 C30 C29 177.9(7) . . . . ?
C7 C8 C9 C1 -1.4(10) . . . . ?
N1 C8 C9 C1 177.1(10) . . . . ?
C2 C1 C9 C8 -179.1(5) . . . . ?
C6 C1 C9 C8 1.5(8) . . . . ?
C17 C16 N2 C23 178.0(5) . . . . ?
C21 C16 N2 C23 -1.4(7) . . . . ?
C22 C23 N2 C16 1.2(8) . . . . ?
C24 C23 N2 C16 -177.0(9) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.048

