# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ic19402
_database_code_depnum_ccdc_archive 'CCDC 1954817'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2020-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N3'
_chemical_formula_weight         363.45

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                   11.6501(4)
_cell_length_b                   10.8130(3)
_cell_length_c                   16.4196(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.886(4)
_cell_angle_gamma                90
_cell_volume                     1979.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4543
_cell_measurement_theta_min      3.8210
_cell_measurement_theta_max      29.0090

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            10903
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4442
_reflns_number_gt                3276
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0944P)²+1.4059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4442
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003

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 0.79410(15) 0.41789(15) 0.35123(10) 0.0259(4) Uani 1 1 d . . . . .
N2 N 0.66748(16) 0.54616(16) 0.39735(11) 0.0281(4) Uani 1 1 d . . . . .
H2 H 0.615(2) 0.553(2) 0.4218(17) 0.042 Uiso 1 1 d . U . . .
N3 N 0.51839(18) 0.36492(17) 0.51346(13) 0.0385(5) Uani 1 1 d . . . . .
C1 C 0.85407(17) 0.30797(18) 0.35683(12) 0.0253(4) Uani 1 1 d . . . . .
C2 C 0.9407(2) 0.2971(2) 0.31214(14) 0.0329(5) Uani 1 1 d . . . . .
H2A H 0.950075 0.361933 0.275529 0.039 Uiso 1 1 calc R U . . .
C3 C 1.0114(2) 0.1934(2) 0.32138(15) 0.0367(5) Uani 1 1 d . . . . .
H3A H 1.070342 0.187740 0.291948 0.044 Uiso 1 1 calc R U . . .
C4 C 0.9972(2) 0.0958(2) 0.37386(14) 0.0347(5) Uani 1 1 d . . . . .
H4A H 1.048474 0.025735 0.381178 0.042 Uiso 1 1 calc R U . . .
C5 C 0.91045(18) 0.10056(19) 0.41451(13) 0.0289(4) Uani 1 1 d . . . . .
H5A H 0.899616 0.032551 0.448157 0.035 Uiso 1 1 calc R U . . .
C6 C 0.83632(17) 0.20662(17) 0.40676(12) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.74710(17) 0.21986(17) 0.45042(11) 0.0234(4) Uani 1 1 d . . . . .
C8 C 0.68991(17) 0.33252(18) 0.44564(12) 0.0240(4) Uani 1 1 d . . . . .
C9 C 0.71903(17) 0.43325(17) 0.39666(11) 0.0236(4) Uani 1 1 d . . . . .
C10 C 0.71628(18) 0.11544(18) 0.49914(12) 0.0260(4) Uani 1 1 d . . . . .
C11 C 0.6765(2) 0.0039(2) 0.45819(14) 0.0332(5) Uani 1 1 d . . . . .
H11A H 0.670304 -0.005566 0.399550 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6459(2) -0.0932(2) 0.50266(17) 0.0437(6) Uani 1 1 d . . . . .
H12A H 0.617874 -0.168771 0.474309 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6559(2) -0.0806(2) 0.58801(17) 0.0472(6) Uani 1 1 d . . . . .
H13A H 0.634702 -0.147540 0.618256 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6969(2) 0.0291(2) 0.62976(15) 0.0435(6) Uani 1 1 d . . . . .
H14A H 0.704461 0.037136 0.688712 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7268(2) 0.1273(2) 0.58543(13) 0.0328(5) Uani 1 1 d . . . . .
H15A H 0.754471 0.202809 0.614024 0.039 Uiso 1 1 calc R U . . .
C16 C 0.59542(19) 0.34922(18) 0.48471(13) 0.0274(4) Uani 1 1 d . . . . .
C17 C 0.69137(18) 0.65107(17) 0.35144(12) 0.0251(4) Uani 1 1 d . . . . .
C18 C 0.80666(18) 0.70086(18) 0.37039(13) 0.0288(5) Uani 1 1 d . . . . .
C19 C 0.82630(19) 0.79867(18) 0.32103(13) 0.0310(5) Uani 1 1 d . . . . .
H19A H 0.905120 0.831234 0.332388 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7352(2) 0.85055(18) 0.25582(13) 0.0303(5) Uani 1 1 d . . . . .
C21 C 0.62017(19) 0.80456(18) 0.24276(13) 0.0293(5) Uani 1 1 d . . . . .
H21A H 0.555665 0.842468 0.201074 0.035 Uiso 1 1 calc R U . . .
C22 C 0.59601(18) 0.70449(18) 0.28880(12) 0.0269(4) Uani 1 1 d . . . . .
C23 C 0.9092(2) 0.6530(2) 0.44282(16) 0.0445(6) Uani 1 1 d . . . . .
H23A H 0.880827 0.584571 0.471070 0.067 Uiso 1 1 calc R U . . .
H23B H 0.973715 0.623686 0.420509 0.067 Uiso 1 1 calc R U . . .
H23C H 0.939408 0.719683 0.483868 0.067 Uiso 1 1 calc R U . . .
C24 C 0.7598(2) 0.9526(2) 0.20006(17) 0.0445(6) Uani 1 1 d . . . . .
H24A H 0.845454 0.973128 0.218477 0.067 Uiso 1 1 calc R U . . .
H24B H 0.737106 0.924726 0.140720 0.067 Uiso 1 1 calc R U . . .
H24C H 0.712902 1.025998 0.204880 0.067 Uiso 1 1 calc R U . . .
C25 C 0.4701(2) 0.6553(2) 0.27013(15) 0.0398(5) Uani 1 1 d . . . . .
H25A H 0.469112 0.585498 0.307986 0.060 Uiso 1 1 calc R U . . .
H25B H 0.417149 0.720782 0.279452 0.060 Uiso 1 1 calc R U . . .
H25C H 0.442147 0.627609 0.210804 0.060 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 C9 1.315(2) . ?
N1 C1 1.368(3) . ?
N2 C9 1.362(3) . ?
N2 C17 1.433(3) . ?
N3 C16 1.142(3) . ?
C1 C2 1.415(3) . ?
C1 C6 1.419(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.365(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.431(3) . ?
C7 C8 1.380(3) . ?
C7 C10 1.487(3) . ?
C8 C16 1.438(3) . ?
C8 C9 1.451(3) . ?
C10 C15 1.392(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.379(4) . ?
C13 C14 1.384(4) . ?
C14 C15 1.389(3) . ?
C17 C18 1.396(3) . ?
C17 C22 1.401(3) . ?
C18 C19 1.391(3) . ?
C18 C23 1.511(3) . ?
C19 C20 1.388(3) . ?
C20 C21 1.387(3) . ?
C20 C24 1.514(3) . ?
C21 C22 1.395(3) . ?
C22 C25 1.506(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
C9 N1 C1 118.85(16) . . ?
C9 N2 C17 123.47(17) . . ?
N1 C1 C2 117.68(17) . . ?
N1 C1 C6 123.53(17) . . ?
C2 C1 C6 118.76(18) . . ?
C3 C2 C1 120.36(19) . . ?
C2 C3 C4 120.6(2) . . ?
C5 C4 C3 120.51(19) . . ?
C4 C5 C6 120.33(19) . . ?
C5 C6 C1 119.26(18) . . ?
C5 C6 C7 123.20(17) . . ?
C1 C6 C7 117.46(17) . . ?
C8 C7 C6 117.95(17) . . ?
C8 C7 C10 120.87(17) . . ?
C6 C7 C10 121.18(17) . . ?
C7 C8 C16 120.34(17) . . ?
C7 C8 C9 120.49(17) . . ?
C16 C8 C9 119.06(17) . . ?
N1 C9 N2 119.05(17) . . ?
N1 C9 C8 121.38(17) . . ?
N2 C9 C8 119.57(17) . . ?
C15 C10 C11 119.32(18) . . ?
C15 C10 C7 120.92(18) . . ?
C11 C10 C7 119.77(17) . . ?
C12 C11 C10 120.2(2) . . ?
C13 C12 C11 120.2(2) . . ?
C12 C13 C14 120.2(2) . . ?
C13 C14 C15 119.9(2) . . ?
C14 C15 C10 120.1(2) . . ?
N3 C16 C8 177.7(2) . . ?
C18 C17 C22 120.75(18) . . ?
C18 C17 N2 120.62(17) . . ?
C22 C17 N2 118.61(18) . . ?
C19 C18 C17 118.28(18) . . ?
C19 C18 C23 119.53(19) . . ?
C17 C18 C23 122.19(19) . . ?
C20 C19 C18 122.57(19) . . ?
C21 C20 C19 117.54(19) . . ?
C21 C20 C24 120.8(2) . . ?
C19 C20 C24 121.6(2) . . ?
C20 C21 C22 122.18(19) . . ?
C21 C22 C17 118.43(19) . . ?
C21 C22 C25 120.11(18) . . ?
C17 C22 C25 121.46(18) . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.055

