# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 2232747'
loop_
_audit_author_name
_audit_author_address
'Yanqing Ge'
;shandong first medical university
China
;
_audit_update_record             
;
2022-12-25 deposited with the CCDC.	2023-08-06 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            'C21 H17 N3'
_chemical_formula_weight         311.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.9292(10)
_cell_length_b                   10.0244(11)
_cell_length_c                   10.3443(12)
_cell_angle_alpha                64.673(2)
_cell_angle_beta                 88.556(2)
_cell_angle_gamma                76.213(2)
_cell_volume                     809.69(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2260
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.63

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.982
_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      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            4135
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2830
_reflns_number_gt                2337
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0587P)²+0.1240P] 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         2830
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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 0.35416(11) 0.29681(12) 0.21233(11) 0.0359(3) Uani 1 1 d . . . . .
N2 N 0.20842(13) 0.28326(16) 0.20239(15) 0.0558(4) Uani 1 1 d . . . . .
C2 C 0.33515(14) 0.54456(14) 0.21890(13) 0.0341(3) Uani 1 1 d . . . . .
C14 C 0.30859(13) 0.31118(14) 0.44155(13) 0.0344(3) Uani 1 1 d . . . . .
C8 C 0.56954(13) 0.32259(14) 0.33660(14) 0.0341(3) Uani 1 1 d . . . . .
C1 C 0.39179(13) 0.37007(14) 0.30368(13) 0.0325(3) Uani 1 1 d . . . . .
N3 N 0.20232(15) 0.22696(17) 0.10955(16) 0.0605(4) Uani 1 1 d . . . . .
C13 C 0.64124(15) 0.22241(16) 0.47166(15) 0.0410(3) Uani 1 1 d . . . . .
H13 H 0.5816 0.1809 0.5464 0.049 Uiso 1 1 calc R U . . .
C3 C 0.20801(15) 0.61353(16) 0.11792(15) 0.0435(3) Uani 1 1 d . . . . .
H3 H 0.1576 0.5532 0.0968 0.052 Uiso 1 1 calc R U . . .
C19 C 0.23482(15) 0.40618(16) 0.50128(15) 0.0432(3) Uani 1 1 d . . . . .
H19 H 0.2322 0.5094 0.4562 0.052 Uiso 1 1 calc R U . . .
C9 C 0.66300(15) 0.38387(16) 0.22771(15) 0.0430(3) Uani 1 1 d . . . . .
H9 H 0.6175 0.4532 0.1363 0.052 Uiso 1 1 calc R U . . .
C15 C 0.31040(15) 0.15706(15) 0.51218(15) 0.0444(3) Uani 1 1 d . . . . .
H15 H 0.3597 0.0912 0.4738 0.053 Uiso 1 1 calc R U . . .
C7 C 0.40600(16) 0.63886(15) 0.24818(14) 0.0423(3) Uani 1 1 d . . . . .
H7 H 0.4914 0.5960 0.3154 0.051 Uiso 1 1 calc R U . . .
C20 C 0.43996(16) 0.24919(16) 0.12462(15) 0.0442(3) Uani 1 1 d . . . . .
H20 H 0.5437 0.2467 0.1105 0.053 Uiso 1 1 calc R U . . .
C6 C 0.35145(18) 0.79549(16) 0.17883(16) 0.0502(4) Uani 1 1 d . . . . .
H6 H 0.4002 0.8569 0.2000 0.060 Uiso 1 1 calc R U . . .
C12 C 0.80119(16) 0.18291(19) 0.49719(17) 0.0532(4) Uani 1 1 d . . . . .
H12 H 0.8474 0.1155 0.5889 0.064 Uiso 1 1 calc R U . . .
C10 C 0.82215(16) 0.34295(18) 0.25382(17) 0.0507(4) Uani 1 1 d . . . . .
H10 H 0.8828 0.3838 0.1797 0.061 Uiso 1 1 calc R U . . .
C11 C 0.89160(16) 0.24212(19) 0.38885(18) 0.0550(4) Uani 1 1 d . . . . .
H11 H 0.9988 0.2145 0.4063 0.066 Uiso 1 1 calc R U . . .
C5 C 0.22621(19) 0.86117(17) 0.07914(16) 0.0540(4) Uani 1 1 d . . . . .
H5 H 0.1898 0.9667 0.0329 0.065 Uiso 1 1 calc R U . . .
C16 C 0.24042(17) 0.10049(18) 0.63792(17) 0.0538(4) Uani 1 1 d . . . . .
H16 H 0.2430 -0.0027 0.6837 0.065 Uiso 1 1 calc R U . . .
C21 C 0.34259(19) 0.20556(18) 0.06095(18) 0.0559(4) Uani 1 1 d . . . . .
H21 H 0.3689 0.1668 -0.0060 0.067 Uiso 1 1 calc R U . . .
C17 C 0.16653(18) 0.1973(2) 0.69571(16) 0.0582(4) Uani 1 1 d . . . . .
H17 H 0.1184 0.1598 0.7801 0.070 Uiso 1 1 calc R U . . .
C4 C 0.15509(18) 0.77062(18) 0.04816(17) 0.0552(4) Uani 1 1 d . . . . .
H4 H 0.0706 0.8148 -0.0202 0.066 Uiso 1 1 calc R U . . .
C18 C 0.16437(18) 0.34901(19) 0.62821(16) 0.0552(4) Uani 1 1 d . . . . .
H18 H 0.1155 0.4141 0.6675 0.066 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 C20 1.3413(17) . ?
N1 N2 1.3511(15) . ?
N1 C1 1.5076(15) . ?
N2 N3 1.3133(17) . ?
C2 C7 1.3875(18) . ?
C2 C3 1.3877(18) . ?
C2 C1 1.5403(17) . ?
C14 C19 1.3808(18) . ?
C14 C15 1.3943(19) . ?
C14 C1 1.5393(17) . ?
C8 C13 1.3815(19) . ?
C8 C9 1.3955(18) . ?
C8 C1 1.5460(16) . ?
N3 C21 1.342(2) . ?
C13 C12 1.3879(18) . ?
C13 H13 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9300 . ?
C19 C18 1.391(2) . ?
C19 H19 0.9300 . ?
C9 C10 1.3811(19) . ?
C9 H9 0.9300 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9300 . ?
C7 C6 1.3808(19) . ?
C7 H7 0.9300 . ?
C20 C21 1.356(2) . ?
C20 H20 0.9300 . ?
C6 C5 1.369(2) . ?
C6 H6 0.9300 . ?
C12 C11 1.369(2) . ?
C12 H12 0.9300 . ?
C10 C11 1.376(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C5 C4 1.365(2) . ?
C5 H5 0.9300 . ?
C16 C17 1.381(2) . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C17 C18 1.370(2) . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C18 H18 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
C20 N1 N2 109.81(11) . . ?
C20 N1 C1 130.83(10) . . ?
N2 N1 C1 119.14(10) . . ?
N3 N2 N1 107.56(11) . . ?
C7 C2 C3 117.56(12) . . ?
C7 C2 C1 120.10(11) . . ?
C3 C2 C1 122.24(11) . . ?
C19 C14 C15 118.10(12) . . ?
C19 C14 C1 121.87(11) . . ?
C15 C14 C1 120.00(11) . . ?
C13 C8 C9 117.83(11) . . ?
C13 C8 C1 122.51(11) . . ?
C9 C8 C1 119.65(11) . . ?
N1 C1 C14 107.32(9) . . ?
N1 C1 C2 108.83(10) . . ?
C14 C1 C2 111.25(9) . . ?
N1 C1 C8 107.49(9) . . ?
C14 C1 C8 111.63(10) . . ?
C2 C1 C8 110.17(10) . . ?
N2 N3 C21 108.18(12) . . ?
C8 C13 C12 120.85(13) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C4 C3 C2 121.08(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C14 C19 C18 120.65(13) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C10 C9 C8 120.91(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C16 C15 C14 121.23(13) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C6 C7 C2 120.91(13) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N1 C20 C21 105.00(12) . . ?
N1 C20 H20 127.5 . . ?
C21 C20 H20 127.5 . . ?
C5 C6 C7 120.58(14) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C11 C12 C13 120.70(14) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C11 C10 C9 120.42(14) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.27(13) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C4 C5 C6 119.52(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C15 C16 C17 119.87(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N3 C21 C20 109.45(13) . . ?
N3 C21 H21 125.3 . . ?
C20 C21 H21 125.3 . . ?
C18 C17 C16 119.72(14) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C5 C4 C3 120.36(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C17 C18 C19 120.44(14) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?

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
C20 N1 N2 N3 0.24(17) . . . . ?
C1 N1 N2 N3 175.45(12) . . . . ?
C20 N1 C1 C14 -144.89(13) . . . . ?
N2 N1 C1 C14 41.08(14) . . . . ?
C20 N1 C1 C2 94.61(15) . . . . ?
N2 N1 C1 C2 -79.42(13) . . . . ?
C20 N1 C1 C8 -24.69(18) . . . . ?
N2 N1 C1 C8 161.28(11) . . . . ?
C19 C14 C1 N1 -138.52(11) . . . . ?
C15 C14 C1 N1 43.47(14) . . . . ?
C19 C14 C1 C2 -19.57(15) . . . . ?
C15 C14 C1 C2 162.42(11) . . . . ?
C19 C14 C1 C8 103.94(13) . . . . ?
C15 C14 C1 C8 -74.06(14) . . . . ?
C7 C2 C1 N1 -153.72(11) . . . . ?
C3 C2 C1 N1 30.09(15) . . . . ?
C7 C2 C1 C14 88.24(13) . . . . ?
C3 C2 C1 C14 -87.95(14) . . . . ?
C7 C2 C1 C8 -36.11(15) . . . . ?
C3 C2 C1 C8 147.70(12) . . . . ?
C13 C8 C1 N1 -109.29(13) . . . . ?
C9 C8 C1 N1 71.77(14) . . . . ?
C13 C8 C1 C14 8.15(16) . . . . ?
C9 C8 C1 C14 -170.79(11) . . . . ?
C13 C8 C1 C2 132.27(12) . . . . ?
C9 C8 C1 C2 -46.67(15) . . . . ?
N1 N2 N3 C21 -0.19(18) . . . . ?
C9 C8 C13 C12 -0.80(19) . . . . ?
C1 C8 C13 C12 -179.76(12) . . . . ?
C7 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 C4 176.90(12) . . . . ?
C15 C14 C19 C18 -0.10(19) . . . . ?
C1 C14 C19 C18 -178.14(12) . . . . ?
C13 C8 C9 C10 1.34(19) . . . . ?
C1 C8 C9 C10 -179.67(12) . . . . ?
C19 C14 C15 C16 0.15(19) . . . . ?
C1 C14 C15 C16 178.23(12) . . . . ?
C3 C2 C7 C6 -0.1(2) . . . . ?
C1 C2 C7 C6 -176.43(12) . . . . ?
N2 N1 C20 C21 -0.20(16) . . . . ?
C1 N1 C20 C21 -174.66(13) . . . . ?
C2 C7 C6 C5 -0.2(2) . . . . ?
C8 C13 C12 C11 -0.2(2) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C13 C12 C11 C10 0.6(2) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C7 C6 C5 C4 -0.1(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
N2 N3 C21 C20 0.07(19) . . . . ?
N1 C20 C21 N3 0.08(18) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C6 C5 C4 C3 0.7(2) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C14 C19 C18 C17 -0.3(2) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2278460'
loop_
_audit_author_name
_audit_author_address
TPA
;shandong first medical university
China
;
_audit_update_record             
;
2023-07-01 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_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         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_chemical_absolute_configuration ?
_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 0.0030 0.0020 '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 0.0060 0.0030 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.183(11)
_cell_length_b                   14.884(11)
_cell_length_c                   7.260(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1437
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.22
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4520
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1079 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.6062.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7907
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.683
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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         0.759
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                1706
_reflns_number_total             2747
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -8.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.1019
_refine_ls_restrained_S_all      1.045
_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)+(0.1997P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2735
_refine_ls_wR_factor_ref         0.3050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C20, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C21, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C8(H8), C2(H2), C18(H18), C14(H14), C12(H12),
 C11(H11), C17(H17), C6(H6), C3(H3), C16(H16), C4(H4), C5(H5), C10(H10),
 C15(H15), C9(H9)
3.b Fitted pentagon refined as free rotating group:
 N1(N2,C20,C21,C22)
;
_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
N1 N 0.2026(3) 0.1768(3) 0.6139(7) 0.0502(17) Uani 1 1 d . . . . .
N2 N 0.1687(4) 0.2628(3) 0.5672(8) 0.077(3) Uani 1 1 d G . . . .
C20 C 0.1077(4) 0.2884(4) 0.7058(11) 0.092(3) Uani 1 1 d G U . . .
H20 H 0.0758 0.3417 0.7093 0.110 Uiso 1 1 calc R . . . .
C21 C 0.1040(4) 0.2183(6) 0.8383(8) 0.102(3) Uani 1 1 d G U . . .
H21 H 0.0692 0.2176 0.9437 0.123 Uiso 1 1 calc R . . . .
C22 C 0.1626(4) 0.1493(5) 0.7815(8) 0.095(4) Uani 1 1 d G U . . .
H22 H 0.1730 0.0956 0.8432 0.114 Uiso 1 1 calc R . . . .
C13 C 0.2106(5) 0.0631(4) 0.3689(9) 0.0420(17) Uani 1 1 d . . . . .
C1 C 0.3249(5) 0.0752(4) 0.6213(10) 0.0419(17) Uani 1 1 d . . . . .
C23 C 0.2630(4) 0.1263(4) 0.4940(11) 0.0389(16) Uani 1 1 d . . . . .
C7 C 0.3143(4) 0.1922(4) 0.3704(10) 0.0410(17) Uani 1 1 d . . . . .
C8 C 0.4006(5) 0.2123(5) 0.3984(12) 0.051(2) Uani 1 1 d . . . . .
H8 H 0.4311 0.1851 0.4945 0.062 Uiso 1 1 calc R . . . .
C2 C 0.3664(6) 0.1200(6) 0.7661(10) 0.057(2) Uani 1 1 d . . . . .
H2 H 0.3543 0.1808 0.7817 0.069 Uiso 1 1 calc R . . . .
C18 C 0.2518(6) 0.0201(6) 0.2267(11) 0.062(2) Uani 1 1 d . . . . .
H18 H 0.3112 0.0302 0.2035 0.074 Uiso 1 1 calc R . . . .
C14 C 0.1218(5) 0.0488(6) 0.3921(13) 0.061(2) Uani 1 1 d . . . . .
H14 H 0.0919 0.0797 0.4842 0.073 Uiso 1 1 calc R . . . .
C12 C 0.2723(6) 0.2316(6) 0.2244(12) 0.063(2) Uani 1 1 d . . . . .
H12 H 0.2139 0.2173 0.1995 0.076 Uiso 1 1 calc R . . . .
C11 C 0.3168(8) 0.2933(6) 0.1120(15) 0.079(3) Uani 1 1 d . . . . .
H11 H 0.2878 0.3204 0.0138 0.094 Uiso 1 1 calc R . . . .
C17 C 0.2035(8) -0.0398(7) 0.1159(14) 0.080(3) Uani 1 1 d . . . . .
H17 H 0.2318 -0.0710 0.0221 0.096 Uiso 1 1 calc R . . . .
C6 C 0.3402(5) -0.0168(5) 0.6057(13) 0.055(2) Uani 1 1 d . . . . .
H6 H 0.3132 -0.0504 0.5136 0.066 Uiso 1 1 calc R . . . .
C3 C 0.4230(6) 0.0807(7) 0.8856(13) 0.069(2) Uani 1 1 d . . . . .
H3 H 0.4504 0.1135 0.9783 0.082 Uiso 1 1 calc R . . . .
C16 C 0.1163(9) -0.0524(7) 0.1441(19) 0.092(4) Uani 1 1 d . . . . .
H16 H 0.0843 -0.0904 0.0676 0.110 Uiso 1 1 calc R . . . .
C4 C 0.4386(6) -0.0103(7) 0.8643(16) 0.079(3) Uani 1 1 d . . . . .
H4 H 0.4780 -0.0394 0.9421 0.095 Uiso 1 1 calc R . . . .
C5 C 0.3970(6) -0.0571(6) 0.7314(13) 0.064(2) Uani 1 1 d . . . . .
H5 H 0.4065 -0.1187 0.7235 0.077 Uiso 1 1 calc R . . . .
C10 C 0.4010(9) 0.3130(7) 0.1467(18) 0.089(4) Uani 1 1 d . . . . .
H10 H 0.4303 0.3549 0.0739 0.107 Uiso 1 1 calc R . . . .
C15 C 0.0766(8) -0.0098(8) 0.2826(17) 0.086(3) Uani 1 1 d . . . . .
H15 H 0.0171 -0.0201 0.3050 0.103 Uiso 1 1 calc R . . . .
C9 C 0.4434(8) 0.2730(6) 0.2848(14) 0.073(3) Uani 1 1 d . . . . .
H9 H 0.5025 0.2860 0.3053 0.088 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 N2 1.4200 . ?
N1 C22 1.4200 . ?
N1 C23 1.471(8) . ?
N2 C20 1.4200 . ?
C20 C21 1.4200 . ?
C21 C22 1.4200 . ?
C13 C23 1.530(10) . ?
C13 C18 1.366(11) . ?
C13 C14 1.376(11) . ?
C1 C23 1.522(10) . ?
C1 C2 1.395(10) . ?
C1 C6 1.394(10) . ?
C23 C7 1.540(9) . ?
C7 C8 1.360(10) . ?
C7 C12 1.369(11) . ?
C8 C9 1.386(11) . ?
C2 C3 1.354(11) . ?
C18 C17 1.407(13) . ?
C14 C15 1.365(13) . ?
C12 C11 1.402(13) . ?
C11 C10 1.336(15) . ?
C17 C16 1.353(15) . ?
C6 C5 1.391(12) . ?
C3 C4 1.383(13) . ?
C16 C15 1.332(16) . ?
C4 C5 1.347(13) . ?
C10 C9 1.332(15) . ?

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
N2 N1 C23 123.1(5) . . ?
C22 N1 N2 108.0 . . ?
C22 N1 C23 128.8(5) . . ?
C20 N2 N1 108.0 . . ?
N2 C20 C21 108.0 . . ?
C22 C21 C20 108.0 . . ?
N1 C22 C21 108.0 . . ?
C18 C13 C23 119.9(7) . . ?
C18 C13 C14 118.0(7) . . ?
C14 C13 C23 122.1(7) . . ?
C2 C1 C23 119.9(6) . . ?
C2 C1 C6 117.1(7) . . ?
C6 C1 C23 123.0(7) . . ?
N1 C23 C13 110.0(5) . . ?
N1 C23 C1 106.3(6) . . ?
N1 C23 C7 109.5(5) . . ?
C13 C23 C7 108.0(6) . . ?
C1 C23 C13 112.0(6) . . ?
C1 C23 C7 111.1(5) . . ?
C8 C7 C23 122.7(6) . . ?
C8 C7 C12 118.0(7) . . ?
C12 C7 C23 119.3(7) . . ?
C7 C8 C9 120.4(8) . . ?
C3 C2 C1 124.2(8) . . ?
C13 C18 C17 119.3(9) . . ?
C15 C14 C13 121.3(9) . . ?
C7 C12 C11 120.5(9) . . ?
C10 C11 C12 119.7(10) . . ?
C16 C17 C18 120.8(10) . . ?
C5 C6 C1 118.2(8) . . ?
C2 C3 C4 117.4(9) . . ?
C15 C16 C17 119.4(11) . . ?
C5 C4 C3 120.4(9) . . ?
C4 C5 C6 122.5(9) . . ?
C11 C10 C9 120.4(11) . . ?
C16 C15 C14 121.1(11) . . ?
C10 C9 C8 120.9(11) . . ?

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 N2 C20 C21 0.0 . . . . ?
N1 C23 C7 C8 106.0(7) . . . . ?
N1 C23 C7 C12 -74.9(9) . . . . ?
N2 N1 C22 C21 0.0 . . . . ?
N2 N1 C23 C13 -92.7(7) . . . . ?
N2 N1 C23 C1 145.9(6) . . . . ?
N2 N1 C23 C7 25.8(8) . . . . ?
N2 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 N1 0.0 . . . . ?
C22 N1 N2 C20 0.0 . . . . ?
C22 N1 C23 C13 81.8(7) . . . . ?
C22 N1 C23 C1 -39.7(7) . . . . ?
C22 N1 C23 C7 -159.8(5) . . . . ?
C13 C23 C7 C8 -134.2(7) . . . . ?
C13 C23 C7 C12 44.8(9) . . . . ?
C13 C18 C17 C16 2.6(13) . . . . ?
C13 C14 C15 C16 -2.9(15) . . . . ?
C1 C23 C7 C8 -11.1(10) . . . . ?
C1 C23 C7 C12 167.9(7) . . . . ?
C1 C2 C3 C4 -1.8(13) . . . . ?
C1 C6 C5 C4 -1.3(13) . . . . ?
C23 N1 N2 C20 175.4(6) . . . . ?
C23 N1 C22 C21 -175.1(7) . . . . ?
C23 C13 C18 C17 178.2(7) . . . . ?
C23 C13 C14 C15 -178.1(8) . . . . ?
C23 C1 C2 C3 -179.4(8) . . . . ?
C23 C1 C6 C5 -178.9(7) . . . . ?
C23 C7 C8 C9 -179.1(7) . . . . ?
C23 C7 C12 C11 178.6(7) . . . . ?
C7 C8 C9 C10 0.2(13) . . . . ?
C7 C12 C11 C10 0.7(14) . . . . ?
C8 C7 C12 C11 -2.3(12) . . . . ?
C2 C1 C23 N1 -48.7(8) . . . . ?
C2 C1 C23 C13 -168.8(6) . . . . ?
C2 C1 C23 C7 70.4(9) . . . . ?
C2 C1 C6 C5 -1.6(11) . . . . ?
C2 C3 C4 C5 -1.3(13) . . . . ?
C18 C13 C23 N1 169.7(6) . . . . ?
C18 C13 C23 C1 -72.3(9) . . . . ?
C18 C13 C23 C7 50.3(8) . . . . ?
C18 C13 C14 C15 3.1(12) . . . . ?
C18 C17 C16 C15 -2.3(16) . . . . ?
C14 C13 C23 N1 -9.0(9) . . . . ?
C14 C13 C23 C1 109.0(8) . . . . ?
C14 C13 C23 C7 -128.4(7) . . . . ?
C14 C13 C18 C17 -2.9(11) . . . . ?
C12 C7 C8 C9 1.9(11) . . . . ?
C12 C11 C10 C9 1.4(16) . . . . ?
C11 C10 C9 C8 -1.8(16) . . . . ?
C17 C16 C15 C14 2.4(16) . . . . ?
C6 C1 C23 N1 128.5(7) . . . . ?
C6 C1 C23 C13 8.4(10) . . . . ?
C6 C1 C23 C7 -112.4(8) . . . . ?
C6 C1 C2 C3 3.2(11) . . . . ?
C3 C4 C5 C6 2.9(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
