# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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. 
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#######################################################################

data_KH29b
_database_code_depnum_ccdc_archive 'CCDC 2076287'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N3'
_chemical_formula_weight         249.31

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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   23.99(2)
_cell_length_b                   38.69(4)
_cell_length_c                   5.573(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5172(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8957
_cell_measurement_theta_min      3.397
_cell_measurement_theta_max      27.428

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8957
_diffrn_reflns_av_unetI/netI     0.1416
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.397
_diffrn_reflns_theta_max         27.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             2733
_reflns_number_gt                1510
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.854
_reflns_Friedel_fraction_full    0.901

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0681P)²+0.7886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   7.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2733
_refine_ls_number_parameters     176
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1794
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.051
_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 0.6476(3) 0.51061(15) 0.7024(13) 0.0244(12) Uani 0.5 1 d D . P A 1
N2 N 0.6594(3) 0.53315(17) 0.8753(13) 0.0244(12) Uani 0.5 1 d D . P A 1
N3 N 0.6238(4) 0.55922(19) 0.8299(17) 0.0325(19) Uani 0.5 1 d D . P A 1
C1 C 0.5048(4) 0.5491(3) 0.2061(18) 0.0393(17) Uiso 0.5 1 d DG . P A 1
H1 H 0.530936 0.530733 0.214639 0.047 Uiso 0.5 1 d R U P A 1
C2 C 0.4652(5) 0.5479(3) 0.022(2) 0.0418(18) Uiso 0.5 1 d D . P A 1
H2 H 0.465112 0.530699 -0.100005 0.050 Uiso 0.5 1 d R U P A 1
C3 C 0.4252(5) 0.5725(3) -0.004(2) 0.0298(16) Uiso 0.5 1 d D . P A 1
H3 H 0.397616 0.574548 -0.124916 0.036 Uiso 0.5 1 d R U P A 1
C4 C 0.4262(6) 0.5981(4) 0.176(2) 0.0342(15) Uiso 0.5 1 d D . P A 1
H4 H 0.401674 0.617347 0.175615 0.041 Uiso 0.5 1 d R U P A 1
C5 C 0.4666(5) 0.6014(3) 0.360(2) 0.0354(17) Uiso 0.5 1 d D . P A 1
H5 H 0.469439 0.620355 0.467667 0.042 Uiso 0.5 1 d R U P A 1
C6 C 0.5078(4) 0.5759(2) 0.3769(17) 0.0310(16) Uiso 0.5 1 d D . P A 1
C7 C 0.5498(4) 0.5785(3) 0.5649(19) 0.0405(15) Uani 0.5 1 d D . P A 1
H7 H 0.549899 0.599490 0.653826 0.049 Uiso 0.5 1 calc R U P A 1
C8 C 0.5897(3) 0.5542(2) 0.6307(15) 0.0325(16) Uani 0.5 1 d D . P A 1
C9 C 0.6067(3) 0.5216(2) 0.5506(18) 0.031(2) Uani 0.5 1 d D . P A 1
H9 H 0.592447 0.509474 0.415825 0.037 Uiso 0.5 1 d R U P A 1
C10 C 0.6774(4) 0.4783(2) 0.6922(15) 0.0272(14) Uiso 0.5 1 d DG . P A 1
C11 C 0.6703(4) 0.4560(2) 0.502(2) 0.0342(16) Uiso 0.5 1 d DG . P A 1
H11 H 0.660220 0.464293 0.348257 0.041 Uiso 0.5 1 d R U P A 1
C12 C 0.6975(5) 0.4245(3) 0.513(2) 0.0362(16) Uiso 0.5 1 d D . P A 1
H12 H 0.692747 0.408925 0.382629 0.043 Uiso 0.5 1 d R U P A 1
C13 C 0.7321(5) 0.4169(3) 0.715(2) 0.0286(14) Uiso 0.5 1 d D . P A 1
H13 H 0.751343 0.395534 0.699956 0.034 Uiso 0.5 1 d R U P A 1
C14 C 0.7389(7) 0.4392(4) 0.905(3) 0.0373(15) Uiso 0.5 1 d D . P A 1
H14 H 0.760868 0.433451 1.041060 0.045 Uiso 0.5 1 calc R U P A 1
C15 C 0.7122(6) 0.4703(3) 0.885(2) 0.0368(15) Uiso 0.5 1 d D . P A 1
H15 H 0.716386 0.485369 1.018551 0.044 Uiso 0.5 1 d R U P A 1
C16 C 0.6226(16) 0.5896(9) 0.991(6) 0.038(3) Uani 0.5 1 d D . P A 1
H16A H 0.633461 0.610308 0.901164 0.057 Uiso 0.5 1 calc R U P A 1
H16B H 0.648791 0.585995 1.123911 0.057 Uiso 0.5 1 calc R U P A 1
H16C H 0.584909 0.592638 1.055227 0.057 Uiso 0.5 1 calc R U P A 1
N1A N 0.5489(3) 0.55891(19) 0.5005(13) 0.0405(15) Uani 0.5 1 d D . P B 2
N2A N 0.5632(4) 0.5838(2) 0.6488(15) 0.0405(15) Uani 0.5 1 d D . P B 2
N3A N 0.6057(4) 0.56924(19) 0.7747(17) 0.0325(19) Uani 0.5 1 d D . P B 2
C1A C 0.6667(5) 0.4631(2) 0.5647(18) 0.0342(16) Uiso 0.5 1 d DG . P B 2
H1A H 0.640689 0.472455 0.454031 0.041 Uiso 0.5 1 d R U P B 2
C2A C 0.6896(5) 0.4305(3) 0.520(3) 0.0362(16) Uiso 0.5 1 d D . P B 2
H2A H 0.680283 0.417695 0.380444 0.043 Uiso 0.5 1 d R U P B 2
C3A C 0.7256(5) 0.4150(3) 0.675(2) 0.0286(14) Uiso 0.5 1 d D . P B 2
H3A H 0.738517 0.391735 0.672935 0.034 Uiso 0.5 1 d R U P B 2
C4A C 0.7413(7) 0.4353(4) 0.873(3) 0.0373(15) Uiso 0.5 1 d D . P B 2
H4A H 0.769076 0.428486 0.984421 0.045 Uiso 0.5 1 d R U P B 2
C5A C 0.7184(5) 0.4680(3) 0.930(2) 0.0368(15) Uiso 0.5 1 d D . P B 2
H5A H 0.730263 0.481548 1.062173 0.044 Uiso 0.5 1 d R U P B 2
C6A C 0.6804(4) 0.4827(2) 0.7686(16) 0.0272(14) Uiso 0.5 1 d D . P B 2
C7A C 0.6592(4) 0.5171(2) 0.827(2) 0.0244(12) Uani 0.5 1 d D . P B 2
H7A H 0.675647 0.528174 0.961482 0.029 Uiso 0.5 1 calc R U P B 2
C8A C 0.6181(3) 0.5356(2) 0.7089(17) 0.0325(16) Uani 0.5 1 d D . P B 2
C9A C 0.5796(3) 0.5292(2) 0.5266(19) 0.031(2) Uani 0.5 1 d D . P B 2
H9A H 0.575410 0.508364 0.438018 0.037 Uiso 0.5 1 d R U P B 2
C10A C 0.5048(4) 0.5654(2) 0.3320(17) 0.0310(16) Uiso 0.5 1 d DG . P B 2
C11A C 0.4981(5) 0.5437(3) 0.1388(18) 0.0393(17) Uiso 0.5 1 d DG . P B 2
H11A H 0.523734 0.525610 0.108462 0.047 Uiso 0.5 1 d R U P B 2
C12A C 0.4538(5) 0.5503(3) -0.014(2) 0.0418(18) Uiso 0.5 1 d D . P B 2
H12A H 0.448256 0.534183 -0.141009 0.050 Uiso 0.5 1 d R U P B 2
C13A C 0.4177(5) 0.5789(3) 0.031(2) 0.0298(16) Uiso 0.5 1 d D . P B 2
H13A H 0.387851 0.580895 -0.079944 0.036 Uiso 0.5 1 d R U P B 2
C14A C 0.4261(6) 0.6015(4) 0.219(2) 0.0342(15) Uiso 0.5 1 d D . P B 2
H14A H 0.398533 0.618827 0.241941 0.041 Uiso 0.5 1 d R U P B 2
C15A C 0.4686(5) 0.5929(3) 0.372(2) 0.0354(17) Uiso 0.5 1 d D . P B 2
H15A H 0.470582 0.607241 0.510158 0.042 Uiso 0.5 1 d R U P B 2
C16A C 0.6306(16) 0.5893(9) 0.974(6) 0.038(3) Uani 0.5 1 d D . P B 2
H16D H 0.670758 0.591809 0.946534 0.057 Uiso 0.5 1 calc R U P B 2
H16E H 0.624253 0.577146 1.125480 0.057 Uiso 0.5 1 calc R U P B 2
H16F H 0.613266 0.612208 0.980628 0.057 Uiso 0.5 1 calc R U P B 2


_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 1.330(8) . ?
N1 C9 1.365(9) . ?
N1 C10 1.440(10) . ?
N2 N3 1.346(9) . ?
N3 C8 1.393(8) . ?
N3 C16 1.480(14) . ?
C1 C2 1.400(14) . ?
C1 C6 1.409(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.358(15) . ?
C2 H2 0.9501 . ?
C3 C4 1.408(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.457(11) . ?
C7 C8 1.391(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(12) . ?
C10 C15 1.396(13) . ?
C11 C12 1.386(14) . ?
C11 H11 0.9475 . ?
C12 C13 1.430(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1A N2A 1.316(8) . ?
N1A C9A 1.373(10) . ?
N1A C10A 1.436(10) . ?
N2A N3A 1.360(9) . ?
N3A C8A 1.385(8) . ?
N3A C16A 1.479(14) . ?
C1A C2A 1.396(14) . ?
C1A C6A 1.405(12) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.360(15) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.406(17) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.416(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.399(13) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.462(11) . ?
C7A C8A 1.382(11) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.395(8) . ?
C9A H9A 0.9499 . ?
C10A C11A 1.376(12) . ?
C10A C15A 1.391(13) . ?
C11A C12A 1.386(14) . ?
C11A H11A 0.9468 . ?
C12A C13A 1.429(15) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.378(17) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.369(17) . ?
C14A H14A 0.9501 . ?
C15A H15A 0.9501 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?

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 C9 113.4(6) . . ?
N2 N1 C10 119.4(7) . . ?
C9 N1 C10 127.2(7) . . ?
N1 N2 N3 102.7(6) . . ?
N2 N3 C8 114.8(6) . . ?
N2 N3 C16 119.5(19) . . ?
C8 N3 C16 125.7(18) . . ?
C2 C1 C6 123.8(9) . . ?
C2 C1 H1 117.4 . . ?
C6 C1 H1 118.8 . . ?
C3 C2 C1 122.1(10) . . ?
C3 C2 H2 114.6 . . ?
C1 C2 H2 123.3 . . ?
C2 C3 C4 114.0(10) . . ?
C2 C3 H3 128.7 . . ?
C4 C3 H3 117.3 . . ?
C3 C4 C5 126.1(11) . . ?
C3 C4 H4 122.7 . . ?
C5 C4 H4 110.7 . . ?
C6 C5 C4 117.9(10) . . ?
C6 C5 H5 116.8 . . ?
C4 C5 H5 125.1 . . ?
C5 C6 C1 115.9(8) . . ?
C5 C6 C7 119.2(8) . . ?
C1 C6 C7 125.0(8) . . ?
C8 C7 C6 128.2(10) . . ?
C8 C7 H7 115.9 . . ?
C6 C7 H7 115.9 . . ?
C7 C8 N3 121.4(7) . . ?
C7 C8 C9 136.6(8) . . ?
N3 C8 C9 102.0(6) . . ?
N1 C9 C8 107.1(6) . . ?
N1 C9 H9 126.5 . . ?
C8 C9 H9 126.4 . . ?
C11 C10 C15 121.8(8) . . ?
C11 C10 N1 120.8(8) . . ?
C15 C10 N1 117.3(8) . . ?
C10 C11 C12 117.4(9) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 117.1 . . ?
C11 C12 C13 119.2(10) . . ?
C11 C12 H12 118.0 . . ?
C13 C12 H12 122.8 . . ?
C14 C13 C12 123.1(10) . . ?
C14 C13 H13 123.8 . . ?
C12 C13 H13 113.0 . . ?
C15 C14 C13 115.8(11) . . ?
C15 C14 H14 122.1 . . ?
C13 C14 H14 122.1 . . ?
C14 C15 C10 122.5(11) . . ?
C14 C15 H15 115.3 . . ?
C10 C15 H15 122.0 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2A N1A C9A 114.0(6) . . ?
N2A N1A C10A 118.3(7) . . ?
C9A N1A C10A 127.6(7) . . ?
N1A N2A N3A 102.5(6) . . ?
N2A N3A C8A 114.5(6) . . ?
N2A N3A C16A 118.1(19) . . ?
C8A N3A C16A 127.3(19) . . ?
C2A C1A C6A 122.6(9) . . ?
C2A C1A H1A 119.2 . . ?
C6A C1A H1A 118.1 . . ?
C3A C2A C1A 122.5(11) . . ?
C3A C2A H2A 116.0 . . ?
C1A C2A H2A 121.6 . . ?
C2A C3A C4A 114.7(10) . . ?
C2A C3A H3A 128.3 . . ?
C4A C3A H3A 116.7 . . ?
C3A C4A C5A 124.9(11) . . ?
C3A C4A H4A 123.2 . . ?
C5A C4A H4A 111.9 . . ?
C6A C5A C4A 118.2(10) . . ?
C6A C5A H5A 118.1 . . ?
C4A C5A H5A 123.4 . . ?
C5A C6A C1A 116.8(8) . . ?
C5A C6A C7A 117.0(8) . . ?
C1A C6A C7A 126.2(8) . . ?
C8A C7A C6A 127.8(9) . . ?
C8A C7A H7A 116.1 . . ?
C6A C7A H7A 116.1 . . ?
C7A C8A N3A 120.8(7) . . ?
C7A C8A C9A 136.6(8) . . ?
N3A C8A C9A 102.6(6) . . ?
N1A C9A C8A 106.5(6) . . ?
N1A C9A H9A 126.8 . . ?
C8A C9A H9A 126.7 . . ?
C11A C10A C15A 121.3(8) . . ?
C11A C10A N1A 119.4(8) . . ?
C15A C10A N1A 119.3(9) . . ?
C10A C11A C12A 117.4(9) . . ?
C10A C11A H11A 121.0 . . ?
C12A C11A H11A 121.6 . . ?
C11A C12A C13A 119.8(10) . . ?
C11A C12A H12A 116.3 . . ?
C13A C12A H12A 123.8 . . ?
C14A C13A C12A 122.6(10) . . ?
C14A C13A H13A 123.7 . . ?
C12A C13A H13A 113.7 . . ?
C15A C14A C13A 115.3(11) . . ?
C15A C14A H14A 127.3 . . ?
C13A C14A H14A 116.5 . . ?
C14A C15A C10A 123.4(10) . . ?
C14A C15A H15A 113.6 . . ?
C10A C15A H15A 122.9 . . ?
N3A C16A H16D 109.5 . . ?
N3A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
N3A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?

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
C9 N1 N2 N3 0.5(11) . . . . ?
C10 N1 N2 N3 -179.3(9) . . . . ?
N1 N2 N3 C8 -0.6(12) . . . . ?
N1 N2 N3 C16 178(2) . . . . ?
C6 C1 C2 C3 -1.5(18) . . . . ?
C1 C2 C3 C4 -2.4(18) . . . . ?
C2 C3 C4 C5 5(2) . . . . ?
C3 C4 C5 C6 -4(2) . . . . ?
C4 C5 C6 C1 -0.2(16) . . . . ?
C4 C5 C6 C7 -179.8(12) . . . . ?
C2 C1 C6 C5 2.8(15) . . . . ?
C2 C1 C6 C7 -177.6(12) . . . . ?
C5 C6 C7 C8 171.4(11) . . . . ?
C1 C6 C7 C8 -8.1(18) . . . . ?
C6 C7 C8 N3 -173.9(11) . . . . ?
C6 C7 C8 C9 3(2) . . . . ?
N2 N3 C8 C7 178.3(10) . . . . ?
C16 N3 C8 C7 0(3) . . . . ?
N2 N3 C8 C9 0.4(12) . . . . ?
C16 N3 C8 C9 -178(2) . . . . ?
N2 N1 C9 C8 -0.3(12) . . . . ?
C10 N1 C9 C8 179.5(8) . . . . ?
C7 C8 C9 N1 -177.5(11) . . . . ?
N3 C8 C9 N1 -0.1(11) . . . . ?
N2 N1 C10 C11 -173.4(9) . . . . ?
C9 N1 C10 C11 6.9(15) . . . . ?
N2 N1 C10 C15 8.4(13) . . . . ?
C9 N1 C10 C15 -171.3(11) . . . . ?
C15 C10 C11 C12 2.4(17) . . . . ?
N1 C10 C11 C12 -175.7(10) . . . . ?
C10 C11 C12 C13 -1.2(18) . . . . ?
C11 C12 C13 C14 1(2) . . . . ?
C12 C13 C14 C15 -3(2) . . . . ?
C13 C14 C15 C10 4(2) . . . . ?
C11 C10 C15 C14 -4(2) . . . . ?
N1 C10 C15 C14 174.4(13) . . . . ?
C9A N1A N2A N3A 0.5(12) . . . . ?
C10A N1A N2A N3A -178.7(9) . . . . ?
N1A N2A N3A C8A -0.3(13) . . . . ?
N1A N2A N3A C16A -176(2) . . . . ?
C6A C1A C2A C3A 2(2) . . . . ?
C1A C2A C3A C4A -5(2) . . . . ?
C2A C3A C4A C5A 7(2) . . . . ?
C3A C4A C5A C6A -5(2) . . . . ?
C4A C5A C6A C1A 1.9(18) . . . . ?
C4A C5A C6A C7A -177.4(12) . . . . ?
C2A C1A C6A C5A -0.4(17) . . . . ?
C2A C1A C6A C7A 178.7(11) . . . . ?
C5A C6A C7A C8A -173.7(11) . . . . ?
C1A C6A C7A C8A 7.1(17) . . . . ?
C6A C7A C8A N3A -174.8(11) . . . . ?
C6A C7A C8A C9A 8.1(19) . . . . ?
N2A N3A C8A C7A -178.0(10) . . . . ?
C16A N3A C8A C7A -3(3) . . . . ?
N2A N3A C8A C9A 0.0(13) . . . . ?
C16A N3A C8A C9A 175(2) . . . . ?
N2A N1A C9A C8A -0.5(12) . . . . ?
C10A N1A C9A C8A 178.6(9) . . . . ?
C7A C8A C9A N1A 177.8(11) . . . . ?
N3A C8A C9A N1A 0.3(11) . . . . ?
N2A N1A C10A C11A 164.1(10) . . . . ?
C9A N1A C10A C11A -15.1(15) . . . . ?
N2A N1A C10A C15A -18.1(14) . . . . ?
C9A N1A C10A C15A 162.7(11) . . . . ?
C15A C10A C11A C12A 0.0(16) . . . . ?
N1A C10A C11A C12A 177.8(11) . . . . ?
C10A C11A C12A C13A 0.5(17) . . . . ?
C11A C12A C13A C14A 2.3(19) . . . . ?
C12A C13A C14A C15A -5(2) . . . . ?
C13A C14A C15A C10A 6(2) . . . . ?
C11A C10A C15A C14A -3.4(19) . . . . ?
N1A C10A C15A C14A 178.8(12) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_wl465
_database_code_depnum_ccdc_archive 'CCDC 2076289'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 N3'
_chemical_formula_weight         305.41

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.464(3)
_cell_length_b                   7.518(2)
_cell_length_c                   12.116(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.972(13)
_cell_angle_gamma                90
_cell_volume                     860.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13047
_cell_measurement_theta_min      3.904
_cell_measurement_theta_max      27.525

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13047
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.904
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             3709
_reflns_number_gt                2861
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.866
_reflns_Friedel_fraction_full    0.916

_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0412P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.049(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3709
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.005
_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 0.54925(16) 0.7098(3) 0.34344(13) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.94452(19) 0.5619(3) 0.54855(17) 0.0300(5) Uani 1 1 d . . . . .
H1 H 0.938398 0.504086 0.478761 0.036 Uiso 1 1 calc R U . . .
N2 N 0.53563(17) 0.6439(3) 0.23923(13) 0.0313(5) Uani 1 1 d . . . . .
C2 C 1.0628(2) 0.5342(3) 0.61836(18) 0.0355(5) Uani 1 1 d . . . . .
H2 H 1.135106 0.456677 0.595690 0.043 Uiso 1 1 calc R U . . .
C3 C 1.0784(2) 0.6168(3) 0.72062(18) 0.0360(6) Uani 1 1 d . . . . .
H3 H 1.159633 0.596215 0.768337 0.043 Uiso 1 1 calc R U . . .
N3 N 0.65170(16) 0.5476(3) 0.23360(13) 0.0288(4) Uani 1 1 d . . . . .
C4 C 0.9720(2) 0.7301(3) 0.75089(16) 0.0349(6) Uani 1 1 d . . . . .
H4 H 0.981145 0.790317 0.819826 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8527(2) 0.7570(3) 0.68249(16) 0.0311(5) Uani 1 1 d . . . . .
H5 H 0.781183 0.834564 0.706404 0.037 Uiso 1 1 calc R U . . .
C6 C 0.83283(19) 0.6735(3) 0.57791(16) 0.0251(5) Uani 1 1 d . . . . .
C7 C 0.70513(19) 0.7087(3) 0.51138(15) 0.0263(5) Uani 1 1 d . . . . .
H7 H 0.635309 0.776981 0.545782 0.032 Uiso 1 1 calc R U . . .
C8 C 0.67140(19) 0.6560(3) 0.40433(16) 0.0259(5) Uani 1 1 d . . . . .
C9 C 0.7366(2) 0.5471(3) 0.32667(15) 0.0280(5) Uani 1 1 d . . . . .
H9 H 0.823741 0.485239 0.337824 0.034 Uiso 1 1 calc R U . . .
C11 C 0.68040(19) 0.4586(3) 0.13105(16) 0.0267(5) Uani 1 1 d . . . . .
C12 C 0.7677(2) 0.5463(3) 0.05944(16) 0.0309(5) Uani 1 1 d . . . . .
C13 C 0.8065(2) 0.4523(3) -0.03318(17) 0.0341(6) Uani 1 1 d . . . . .
H13 H 0.867625 0.507191 -0.082832 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7585(2) 0.2808(3) -0.05520(17) 0.0344(6) Uani 1 1 d . . . . .
C15 C 0.6643(2) 0.2059(3) 0.01537(17) 0.0345(5) Uani 1 1 d . . . . .
H15 H 0.625598 0.092155 -0.002036 0.041 Uiso 1 1 calc R U . . .
C16 C 0.6243(2) 0.2915(3) 0.11091(17) 0.0315(5) Uani 1 1 d . . . . .
C17 C 0.8152(3) 0.7329(3) 0.0801(2) 0.0459(7) Uani 1 1 d . . . . .
H17A H 0.880947 0.767906 0.024130 0.069 Uiso 1 1 calc R U . . .
H17B H 0.862837 0.741202 0.153675 0.069 Uiso 1 1 calc R U . . .
H17C H 0.732935 0.812271 0.076075 0.069 Uiso 1 1 calc R U . . .
C18 C 0.8086(2) 0.1779(4) -0.15164(19) 0.0485(7) Uani 1 1 d . . . . .
H18A H 0.728974 0.112384 -0.186981 0.073 Uiso 1 1 calc R U . . .
H18B H 0.882303 0.093904 -0.125925 0.073 Uiso 1 1 calc R U . . .
H18C H 0.847201 0.260231 -0.205102 0.073 Uiso 1 1 calc R U . . .
C19 C 0.5264(2) 0.2038(4) 0.1880(2) 0.0478(7) Uani 1 1 d . . . . .
H19A H 0.508998 0.080673 0.164469 0.072 Uiso 1 1 calc R U . . .
H19B H 0.436519 0.268784 0.186557 0.072 Uiso 1 1 calc R U . . .
H19C H 0.569666 0.204792 0.263235 0.072 Uiso 1 1 calc R U . . .
C20 C 0.4357(2) 0.8219(3) 0.38086(17) 0.0319(5) Uani 1 1 d . . . . .
H20A H 0.382308 0.872205 0.315688 0.038 Uiso 1 1 calc R U . . .
H20B H 0.477267 0.922213 0.424372 0.038 Uiso 1 1 calc R U . . .
C21 C 0.3344(2) 0.7213(3) 0.45106(18) 0.0353(5) Uani 1 1 d . . . . .
H21A H 0.293148 0.621452 0.408564 0.053 Uiso 1 1 calc R U . . .
H21B H 0.258759 0.801425 0.472414 0.053 Uiso 1 1 calc R U . . .
H21C H 0.385681 0.676167 0.517589 0.053 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 N2 1.356(2) . ?
N1 C8 1.398(3) . ?
N1 C20 1.457(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.409(3) . ?
C1 H1 0.9500 . ?
N2 N3 1.320(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
N3 C9 1.350(2) . ?
N3 C11 1.449(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.418(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.442(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.413(3) . ?
C9 H9 0.9500 . ?
C11 C16 1.380(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.391(3) . ?
C12 C17 1.490(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 C18 1.498(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C19 1.502(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.516(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 C8 114.95(16) . . ?
N2 N1 C20 117.70(16) . . ?
C8 N1 C20 127.31(16) . . ?
C2 C1 C6 121.95(19) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
N3 N2 N1 102.06(15) . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
N2 N3 C9 114.80(16) . . ?
N2 N3 C11 119.40(16) . . ?
C9 N3 C11 125.76(16) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 122.6(2) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C5 114.99(18) . . ?
C1 C6 C7 125.87(18) . . ?
C5 C6 C7 119.13(18) . . ?
C8 C7 C6 128.33(18) . . ?
C8 C7 H7 115.8 . . ?
C6 C7 H7 115.8 . . ?
C7 C8 N1 123.96(17) . . ?
C7 C8 C9 134.86(18) . . ?
N1 C8 C9 101.19(16) . . ?
N3 C9 C8 107.00(17) . . ?
N3 C9 H9 126.5 . . ?
C8 C9 H9 126.5 . . ?
C16 C11 C12 123.71(18) . . ?
C16 C11 N3 118.98(18) . . ?
C12 C11 N3 117.28(19) . . ?
C13 C12 C11 116.8(2) . . ?
C13 C12 C17 121.6(2) . . ?
C11 C12 C17 121.6(2) . . ?
C14 C13 C12 121.9(2) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C15 C14 C13 118.2(2) . . ?
C15 C14 C18 120.7(2) . . ?
C13 C14 C18 121.1(2) . . ?
C14 C15 C16 122.4(2) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C11 C16 C15 116.63(19) . . ?
C11 C16 C19 122.24(19) . . ?
C15 C16 C19 121.1(2) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 112.61(18) . . ?
N1 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N1 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C8 N1 N2 N3 -0.4(2) . . . . ?
C20 N1 N2 N3 -178.51(17) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
N1 N2 N3 C9 0.4(2) . . . . ?
N1 N2 N3 C11 -177.51(18) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C7 -179.98(19) . . . . ?
C1 C6 C7 C8 -6.4(3) . . . . ?
C5 C6 C7 C8 173.0(2) . . . . ?
C6 C7 C8 N1 -174.34(19) . . . . ?
C6 C7 C8 C9 4.9(4) . . . . ?
N2 N1 C8 C7 179.72(19) . . . . ?
C20 N1 C8 C7 -2.4(3) . . . . ?
N2 N1 C8 C9 0.3(2) . . . . ?
C20 N1 C8 C9 178.13(19) . . . . ?
N2 N3 C9 C8 -0.3(3) . . . . ?
C11 N3 C9 C8 177.5(2) . . . . ?
C7 C8 C9 N3 -179.3(2) . . . . ?
N1 C8 C9 N3 0.0(2) . . . . ?
N2 N3 C11 C16 -86.8(2) . . . . ?
C9 N3 C11 C16 95.5(2) . . . . ?
N2 N3 C11 C12 95.1(2) . . . . ?
C9 N3 C11 C12 -82.6(3) . . . . ?
C16 C11 C12 C13 -4.4(3) . . . . ?
N3 C11 C12 C13 173.55(17) . . . . ?
C16 C11 C12 C17 174.5(2) . . . . ?
N3 C11 C12 C17 -7.5(3) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C17 C12 C13 C14 -177.6(2) . . . . ?
C12 C13 C14 C15 2.9(3) . . . . ?
C12 C13 C14 C18 -176.2(2) . . . . ?
C13 C14 C15 C16 -4.6(3) . . . . ?
C18 C14 C15 C16 174.6(2) . . . . ?
C12 C11 C16 C15 2.9(3) . . . . ?
N3 C11 C16 C15 -175.03(18) . . . . ?
C12 C11 C16 C19 -177.7(2) . . . . ?
N3 C11 C16 C19 4.3(3) . . . . ?
C14 C15 C16 C11 1.7(3) . . . . ?
C14 C15 C16 C19 -177.6(2) . . . . ?
N2 N1 C20 C21 99.1(2) . . . . ?
C8 N1 C20 C21 -78.7(3) . . . . ?

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.030



####################################################################### 
# 
# 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_wl479
_database_code_depnum_ccdc_archive 'CCDC 2076292'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 F N3'
_chemical_formula_weight         267.30

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   11.0959(5)
_cell_length_b                   15.0897(7)
_cell_length_c                   16.0556(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2688.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    149(2)
_cell_measurement_reflns_used    20602
_cell_measurement_theta_min      2.700
_cell_measurement_theta_max      27.503

_exptl_crystal_description       block
_exptl_crystal_colour            'dark blue purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6866
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      149(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20602
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.700
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6147
_reflns_number_gt                5227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.996

_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0489P)²] 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 2025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6147
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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
F1 F 0.45892(10) 0.58330(9) 0.58842(8) 0.0524(3) Uani 1 1 d . . . . .
N1 N -0.03192(14) 0.53967(10) 0.90594(9) 0.0316(4) Uani 1 1 d . . . . .
C1 C -0.26390(16) 0.38103(12) 0.73203(11) 0.0303(4) Uani 1 1 d . . . . .
H1 H -0.184775 0.390739 0.711342 0.036 Uiso 1 1 calc R U . . .
F2 F 1.32584(13) 0.66048(9) 0.40475(8) 0.0562(4) Uani 1 1 d . . . . .
N2 N 0.07903(14) 0.56213(10) 0.87942(9) 0.0321(4) Uani 1 1 d . . . . .
C2 C -0.34696(16) 0.33762(13) 0.68203(11) 0.0331(4) Uani 1 1 d . . . . .
H2 H -0.323090 0.317536 0.628430 0.040 Uiso 1 1 calc R U . . .
N3 N 0.08517(13) 0.52258(10) 0.80611(9) 0.0291(3) Uani 1 1 d . . . . .
C3 C -0.46384(17) 0.32297(13) 0.70860(13) 0.0365(4) Uani 1 1 d . . . . .
H3 H -0.520585 0.293820 0.673776 0.044 Uiso 1 1 calc R U . . .
N4 N 0.80876(13) 0.64909(10) 0.70488(9) 0.0307(3) Uani 1 1 d . . . . .
C4 C -0.49602(18) 0.35210(13) 0.78778(14) 0.0406(5) Uani 1 1 d . . . . .
H4 H -0.575999 0.343094 0.807131 0.049 Uiso 1 1 calc R U . . .
N5 N 0.86921(13) 0.63022(10) 0.63446(9) 0.0320(4) Uani 1 1 d . . . . .
C5 C -0.41353(17) 0.39380(13) 0.83846(12) 0.0375(5) Uani 1 1 d . . . . .
H5 H -0.437935 0.411566 0.892663 0.045 Uiso 1 1 calc R U . . .
N6 N 0.97168(13) 0.67366(10) 0.64455(9) 0.0282(3) Uani 1 1 d . . . . .
C6 C -0.29334(16) 0.41129(12) 0.81282(11) 0.0305(4) Uani 1 1 d . . . . .
C7 C -0.21509(17) 0.45937(12) 0.86753(11) 0.0322(4) Uani 1 1 d . . . . .
H7 H -0.246652 0.474011 0.920779 0.039 Uiso 1 1 calc R U . . .
C8 C -0.09785(17) 0.48694(12) 0.85106(11) 0.0293(4) Uani 1 1 d . . . . .
C9 C -0.01522(16) 0.47690(12) 0.78518(11) 0.0289(4) Uani 1 1 d . . . . .
H9 H -0.027655 0.444175 0.735371 0.035 Uiso 1 1 calc R U . . .
C10 C 0.18903(15) 0.53622(12) 0.75462(11) 0.0293(4) Uani 1 1 d . . . . .
C11 C 0.24372(15) 0.61864(12) 0.75306(12) 0.0308(4) Uani 1 1 d . . . . .
H11 H 0.217730 0.664075 0.789868 0.037 Uiso 1 1 calc R U . . .
C12 C 0.33694(16) 0.63439(13) 0.69720(12) 0.0361(4) Uani 1 1 d . . . . .
H12 H 0.375818 0.690433 0.694928 0.043 Uiso 1 1 calc R U . . .
C13 C 0.37112(16) 0.56667(14) 0.64550(13) 0.0382(5) Uani 1 1 d . . . . .
C14 C 0.31988(17) 0.48352(14) 0.64786(13) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.347509 0.437976 0.611741 0.048 Uiso 1 1 calc R U . . .
C15 C 0.22779(17) 0.46757(13) 0.70356(13) 0.0357(4) Uani 1 1 d . . . . .
H15 H 0.191514 0.410657 0.706955 0.043 Uiso 1 1 calc R U . . .
C16 C -0.0757(2) 0.57671(13) 0.98381(11) 0.0377(5) Uani 1 1 d . . . . .
H16A H -0.149484 0.610647 0.973382 0.057 Uiso 1 1 calc R U . . .
H16B H -0.014173 0.615857 1.007535 0.057 Uiso 1 1 calc R U . . .
H16C H -0.093010 0.528591 1.023024 0.057 Uiso 1 1 calc R U . . .
C17 C 1.00664(17) 0.80108(12) 0.90027(11) 0.0316(4) Uani 1 1 d . . . . .
H17 H 1.054993 0.783487 0.854322 0.038 Uiso 1 1 calc R U . . .
C18 C 1.06018(19) 0.84629(13) 0.96576(11) 0.0370(5) Uani 1 1 d . . . . .
H18 H 1.143834 0.859436 0.963275 0.044 Uiso 1 1 calc R U . . .
C19 C 0.9940(2) 0.87276(13) 1.03496(12) 0.0415(5) Uani 1 1 d . . . . .
H19 H 1.031114 0.903122 1.080019 0.050 Uiso 1 1 calc R U . . .
C20 C 0.8715(2) 0.85313(13) 1.03577(12) 0.0432(5) Uani 1 1 d . . . . .
H20 H 0.824160 0.870587 1.082268 0.052 Uiso 1 1 calc R U . . .
C21 C 0.8173(2) 0.80906(13) 0.97086(12) 0.0376(5) Uani 1 1 d . . . . .
H21 H 0.733254 0.797433 0.973766 0.045 Uiso 1 1 calc R U . . .
C22 C 0.88216(16) 0.78033(12) 0.89972(11) 0.0292(4) Uani 1 1 d . . . . .
C23 C 0.82149(16) 0.73290(12) 0.83509(11) 0.0309(4) Uani 1 1 d . . . . .
H23 H 0.739189 0.718944 0.844766 0.037 Uiso 1 1 calc R U . . .
C24 C 0.86951(15) 0.70505(12) 0.75991(11) 0.0284(4) Uani 1 1 d . . . . .
C25 C 0.97825(16) 0.71896(12) 0.71683(11) 0.0284(4) Uani 1 1 d . . . . .
H25 H 1.044282 0.753895 0.735275 0.034 Uiso 1 1 calc R U . . .
C26 C 1.06191(17) 0.66996(12) 0.58058(10) 0.0291(4) Uani 1 1 d . . . . .
C27 C 1.1263(2) 0.74640(13) 0.56241(11) 0.0385(5) Uani 1 1 d . . . . .
H27 H 1.108963 0.800245 0.590629 0.046 Uiso 1 1 calc R U . . .
C28 C 1.2158(2) 0.74324(15) 0.50291(12) 0.0435(5) Uani 1 1 d . . . . .
H28 H 1.261506 0.794561 0.489542 0.052 Uiso 1 1 calc R U . . .
C29 C 1.2374(2) 0.66393(14) 0.46341(12) 0.0400(5) Uani 1 1 d . . . . .
C30 C 1.17487(18) 0.58793(13) 0.48049(11) 0.0365(4) Uani 1 1 d . . . . .
H30 H 1.192530 0.534422 0.451811 0.044 Uiso 1 1 calc R U . . .
C31 C 1.08515(17) 0.59069(13) 0.54057(11) 0.0318(4) Uani 1 1 d . . . . .
H31 H 1.040420 0.538948 0.554001 0.038 Uiso 1 1 calc R U . . .
C32 C 0.68589(16) 0.61705(14) 0.71394(14) 0.0399(5) Uani 1 1 d . . . . .
H32A H 0.629900 0.667199 0.711259 0.060 Uiso 1 1 calc R U . . .
H32B H 0.677267 0.587073 0.767761 0.060 Uiso 1 1 calc R U . . .
H32C H 0.667678 0.575292 0.668925 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
F1 C13 1.361(2) . ?
N1 N2 1.346(2) . ?
N1 C8 1.394(2) . ?
N1 C16 1.453(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.414(2) . ?
C1 H1 0.9500 . ?
F2 C29 1.361(2) . ?
N2 N3 1.321(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
N3 C9 1.352(2) . ?
N3 C10 1.433(2) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
N4 N5 1.345(2) . ?
N4 C24 1.396(2) . ?
N4 C32 1.454(2) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
N5 N6 1.322(2) . ?
C5 C6 1.420(3) . ?
C5 H5 0.9500 . ?
N6 C25 1.349(2) . ?
N6 C26 1.435(2) . ?
C6 C7 1.432(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.387(3) . ?
C17 C22 1.416(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.418(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.429(3) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.406(2) . ?
C25 H25 0.9500 . ?
C26 C31 1.382(3) . ?
C26 C27 1.388(3) . ?
C27 C28 1.379(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.368(3) . ?
C30 C31 1.387(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

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 C8 115.07(14) . . ?
N2 N1 C16 118.76(15) . . ?
C8 N1 C16 125.99(16) . . ?
C2 C1 C6 122.03(17) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
N3 N2 N1 102.42(14) . . ?
C3 C2 C1 121.34(18) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N2 N3 C9 114.15(15) . . ?
N2 N3 C10 119.36(15) . . ?
C9 N3 C10 126.32(14) . . ?
C2 C3 C4 118.16(19) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
N5 N4 C24 114.79(14) . . ?
N5 N4 C32 118.78(16) . . ?
C24 N4 C32 126.21(16) . . ?
C5 C4 C3 120.90(19) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N6 N5 N4 102.76(14) . . ?
C4 C5 C6 122.54(18) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
N5 N6 C25 113.77(15) . . ?
N5 N6 C26 119.52(14) . . ?
C25 N6 C26 126.71(15) . . ?
C1 C6 C5 115.02(17) . . ?
C1 C6 C7 125.89(17) . . ?
C5 C6 C7 119.05(17) . . ?
C8 C7 C6 127.00(17) . . ?
C8 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
C7 C8 N1 122.76(16) . . ?
C7 C8 C9 136.02(17) . . ?
N1 C8 C9 101.21(15) . . ?
N3 C9 C8 107.15(15) . . ?
N3 C9 H9 126.4 . . ?
C8 C9 H9 126.4 . . ?
C11 C10 C15 121.57(17) . . ?
C11 C10 N3 119.48(16) . . ?
C15 C10 N3 118.83(17) . . ?
C10 C11 C12 119.46(18) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.00(19) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
F1 C13 C12 117.94(19) . . ?
F1 C13 C14 118.80(17) . . ?
C12 C13 C14 123.25(19) . . ?
C13 C14 C15 118.84(18) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C10 118.81(18) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 122.08(18) . . ?
C18 C17 H17 119.0 . . ?
C22 C17 H17 119.0 . . ?
C17 C18 C19 121.40(19) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 117.52(19) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C21 C20 C19 121.55(18) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 122.4(2) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C17 C22 C21 114.99(18) . . ?
C17 C22 C23 125.07(16) . . ?
C21 C22 C23 119.93(17) . . ?
C24 C23 C22 127.14(17) . . ?
C24 C23 H23 116.4 . . ?
C22 C23 H23 116.4 . . ?
C23 C24 N4 123.34(16) . . ?
C23 C24 C25 135.52(17) . . ?
N4 C24 C25 101.14(15) . . ?
N6 C25 C24 107.53(15) . . ?
N6 C25 H25 126.2 . . ?
C24 C25 H25 126.2 . . ?
C31 C26 C27 121.70(17) . . ?
C31 C26 N6 119.77(16) . . ?
C27 C26 N6 118.50(17) . . ?
C28 C27 C26 119.19(19) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C29 C28 C27 118.3(2) . . ?
C29 C28 H28 120.8 . . ?
C27 C28 H28 120.8 . . ?
F2 C29 C30 118.18(19) . . ?
F2 C29 C28 118.53(19) . . ?
C30 C29 C28 123.29(19) . . ?
C29 C30 C31 118.57(19) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C26 C31 C30 118.90(18) . . ?
C26 C31 H31 120.6 . . ?
C30 C31 H31 120.6 . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

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
C8 N1 N2 N3 -0.40(19) . . . . ?
C16 N1 N2 N3 -175.76(15) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
N1 N2 N3 C9 0.09(18) . . . . ?
N1 N2 N3 C10 175.60(14) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C24 N4 N5 N6 0.89(19) . . . . ?
C32 N4 N5 N6 175.78(15) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
N4 N5 N6 C25 -0.44(18) . . . . ?
N4 N5 N6 C26 -179.73(14) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -177.61(17) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 176.54(17) . . . . ?
C1 C6 C7 C8 1.7(3) . . . . ?
C5 C6 C7 C8 -175.90(18) . . . . ?
C6 C7 C8 N1 174.75(17) . . . . ?
C6 C7 C8 C9 -3.8(3) . . . . ?
N2 N1 C8 C7 -178.42(15) . . . . ?
C16 N1 C8 C7 -3.4(3) . . . . ?
N2 N1 C8 C9 0.54(19) . . . . ?
C16 N1 C8 C9 175.51(16) . . . . ?
N2 N3 C9 C8 0.2(2) . . . . ?
C10 N3 C9 C8 -174.91(16) . . . . ?
C7 C8 C9 N3 178.3(2) . . . . ?
N1 C8 C9 N3 -0.44(18) . . . . ?
N2 N3 C10 C11 -36.7(2) . . . . ?
C9 N3 C10 C11 138.23(18) . . . . ?
N2 N3 C10 C15 147.21(16) . . . . ?
C9 N3 C10 C15 -37.9(2) . . . . ?
C15 C10 C11 C12 2.2(3) . . . . ?
N3 C10 C11 C12 -173.75(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 F1 177.27(16) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
F1 C13 C14 C15 -177.61(16) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C11 C10 C15 C14 -2.6(3) . . . . ?
N3 C10 C15 C14 173.43(16) . . . . ?
C22 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C18 C17 C22 C21 -0.1(3) . . . . ?
C18 C17 C22 C23 -179.02(17) . . . . ?
C20 C21 C22 C17 -0.5(3) . . . . ?
C20 C21 C22 C23 178.48(16) . . . . ?
C17 C22 C23 C24 -5.3(3) . . . . ?
C21 C22 C23 C24 175.81(17) . . . . ?
C22 C23 C24 N4 171.31(16) . . . . ?
C22 C23 C24 C25 -8.5(3) . . . . ?
N5 N4 C24 C23 179.17(15) . . . . ?
C32 N4 C24 C23 4.7(3) . . . . ?
N5 N4 C24 C25 -0.96(19) . . . . ?
C32 N4 C24 C25 -175.41(16) . . . . ?
N5 N6 C25 C24 -0.1(2) . . . . ?
C26 N6 C25 C24 179.09(15) . . . . ?
C23 C24 C25 N6 -179.54(19) . . . . ?
N4 C24 C25 N6 0.62(18) . . . . ?
N5 N6 C26 C31 -41.0(2) . . . . ?
C25 N6 C26 C31 139.82(18) . . . . ?
N5 N6 C26 C27 140.95(17) . . . . ?
C25 N6 C26 C27 -38.2(3) . . . . ?
C31 C26 C27 C28 0.0(3) . . . . ?
N6 C26 C27 C28 178.02(18) . . . . ?
C26 C27 C28 C29 0.3(3) . . . . ?
C27 C28 C29 F2 -179.87(19) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
F2 C29 C30 C31 179.56(17) . . . . ?
C28 C29 C30 C31 0.0(3) . . . . ?
C27 C26 C31 C30 -0.3(3) . . . . ?
N6 C26 C31 C30 -178.31(16) . . . . ?
C29 C30 C31 C26 0.3(3) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_wl438
_database_code_depnum_ccdc_archive 'CCDC 2076293'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N5'
_chemical_formula_weight         317.39

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                   8.704(3)
_cell_length_b                   15.441(5)
_cell_length_c                   12.626(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.212(17)
_cell_angle_gamma                90
_cell_volume                     1696.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18038
_cell_measurement_theta_min      2.638
_cell_measurement_theta_max      27.460

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18038
_diffrn_reflns_av_unetI/netI     0.1079
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3847
_reflns_number_gt                2386
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0372P)²+0.1692P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3847
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.1859(2) 0.31778(12) 0.00238(15) 0.0387(5) Uani 1 1 d . . . . .
H1A H 0.197954 0.279260 0.060630 0.046 Uiso 1 1 calc R U . . .
N1 N 0.3158(2) 0.60016(10) 0.15964(13) 0.0455(5) Uani 1 1 d . . . . .
N2 N 0.3390(2) 0.64040(11) 0.25137(13) 0.0461(5) Uani 1 1 d . . . . .
C2 C 0.1713(2) 0.28457(13) -0.09836(15) 0.0422(5) Uani 1 1 d . . . . .
H2A H 0.173494 0.223713 -0.109294 0.051 Uiso 1 1 calc R U . . .
N3 N 0.28859(17) 0.58577(10) 0.32589(12) 0.0333(4) Uani 1 1 d . . . . .
C3 C 0.1535(2) 0.34028(13) -0.18406(16) 0.0432(5) Uani 1 1 d . . . . .
H3A H 0.143139 0.317509 -0.253749 0.052 Uiso 1 1 calc R U . . .
C4 C 0.1507(2) 0.42869(14) -0.16813(16) 0.0436(5) Uani 1 1 d . . . . .
H4A H 0.139284 0.466707 -0.226927 0.052 Uiso 1 1 calc R U . . .
N4 N 0.15166(17) 0.39243(10) 0.21256(12) 0.0340(4) Uani 1 1 d . . . . .
C5 C 0.1645(2) 0.46212(12) -0.06640(15) 0.0384(5) Uani 1 1 d . . . . .
H5A H 0.161260 0.523025 -0.055997 0.046 Uiso 1 1 calc R U . . .
N5 N 0.17381(16) 0.43509(10) 0.30831(11) 0.0329(4) Uani 1 1 d . . . . .
C6 C 0.18322(19) 0.40725(11) 0.02098(14) 0.0312(4) Uani 1 1 d . . . . .
C7 C 0.19590(19) 0.44061(12) 0.12952(14) 0.0310(4) Uani 1 1 d . . . . .
C8 C 0.2489(2) 0.52052(11) 0.17160(14) 0.0327(4) Uani 1 1 d . . . . .
C9 C 0.23306(18) 0.51118(11) 0.27943(14) 0.0284(4) Uani 1 1 d . . . . .
C10 C 0.3112(2) 0.60549(11) 0.43647(14) 0.0313(4) Uani 1 1 d . . . . .
C11 C 0.1823(2) 0.61197(11) 0.49966(15) 0.0320(4) Uani 1 1 d . . . . .
C12 C 0.2058(2) 0.62405(12) 0.60742(15) 0.0363(5) Uani 1 1 d . . . . .
H12A H 0.119485 0.628501 0.651867 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3534(2) 0.62987(12) 0.65241(16) 0.0376(5) Uani 1 1 d . . . . .
C14 C 0.4781(2) 0.62552(12) 0.58609(17) 0.0405(5) Uani 1 1 d . . . . .
H14A H 0.578637 0.631534 0.615963 0.049 Uiso 1 1 calc R U . . .
C15 C 0.4615(2) 0.61270(12) 0.47768(17) 0.0374(5) Uani 1 1 d . . . . .
C16 C 0.0220(2) 0.60736(14) 0.45271(16) 0.0443(5) Uani 1 1 d . . . . .
H16A H -0.052745 0.609506 0.509642 0.066 Uiso 1 1 calc R U . . .
H16B H 0.009384 0.553097 0.413218 0.066 Uiso 1 1 calc R U . . .
H16C H 0.004964 0.656480 0.404732 0.066 Uiso 1 1 calc R U . . .
C17 C 0.3773(3) 0.63922(14) 0.77089(17) 0.0545(6) Uani 1 1 d . . . . .
H17A H 0.284841 0.664087 0.801723 0.082 Uiso 1 1 calc R U . . .
H17B H 0.465142 0.677447 0.785449 0.082 Uiso 1 1 calc R U . . .
H17C H 0.397499 0.582172 0.802235 0.082 Uiso 1 1 calc R U . . .
C18 C 0.6002(2) 0.60522(14) 0.40906(19) 0.0534(6) Uani 1 1 d . . . . .
H18A H 0.586070 0.556767 0.359680 0.080 Uiso 1 1 calc R U . . .
H18B H 0.691798 0.595000 0.453794 0.080 Uiso 1 1 calc R U . . .
H18C H 0.613052 0.659024 0.369043 0.080 Uiso 1 1 calc R U . . .
C19 C 0.3635(4) 0.64479(15) 0.06318(18) 0.0814(10) Uani 1 1 d . . . . .
H19A H 0.416092 0.603769 0.017091 0.122 Uiso 1 1 calc R U . . .
H19B H 0.433530 0.692266 0.082212 0.122 Uiso 1 1 calc R U . . .
H19C H 0.272801 0.668135 0.025796 0.122 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 1.375(3) . ?
C1 C6 1.402(2) . ?
C1 H1A 0.9500 . ?
N1 N2 1.326(2) . ?
N1 C8 1.370(2) . ?
N1 C19 1.467(3) . ?
N2 N3 1.344(2) . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9500 . ?
N3 C9 1.376(2) . ?
N3 C10 1.438(2) . ?
C3 C4 1.380(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9500 . ?
N4 C7 1.348(2) . ?
N4 N5 1.387(2) . ?
C5 C6 1.398(2) . ?
C5 H5A 0.9500 . ?
N5 C9 1.337(2) . ?
C6 C7 1.466(2) . ?
C7 C8 1.417(2) . ?
C8 C9 1.379(2) . ?
C10 C11 1.394(3) . ?
C10 C15 1.402(3) . ?
C11 C12 1.384(3) . ?
C11 C16 1.506(2) . ?
C12 C13 1.396(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(3) . ?
C13 C17 1.513(3) . ?
C14 C15 1.388(3) . ?
C14 H14A 0.9500 . ?
C15 C18 1.505(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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 121.41(17) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
N2 N1 C8 112.42(16) . . ?
N2 N1 C19 117.67(16) . . ?
C8 N1 C19 129.90(17) . . ?
N1 N2 N3 105.75(15) . . ?
C1 C2 C3 119.77(19) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
N2 N3 C9 110.11(15) . . ?
N2 N3 C10 120.43(15) . . ?
C9 N3 C10 129.11(15) . . ?
C4 C3 C2 120.08(19) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.11(18) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C7 N4 N5 112.28(14) . . ?
C4 C5 C6 120.77(18) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C9 N5 N4 103.12(14) . . ?
C5 C6 C1 117.85(17) . . ?
C5 C6 C7 122.01(17) . . ?
C1 C6 C7 120.12(16) . . ?
N4 C7 C8 106.56(15) . . ?
N4 C7 C6 121.06(16) . . ?
C8 C7 C6 132.38(16) . . ?
N1 C8 C9 104.74(15) . . ?
N1 C8 C7 151.17(18) . . ?
C9 C8 C7 103.92(15) . . ?
N5 C9 N3 138.91(17) . . ?
N5 C9 C8 114.11(16) . . ?
N3 C9 C8 106.97(15) . . ?
C11 C10 C15 122.53(18) . . ?
C11 C10 N3 118.37(15) . . ?
C15 C10 N3 119.00(17) . . ?
C12 C11 C10 117.89(16) . . ?
C12 C11 C16 120.67(18) . . ?
C10 C11 C16 121.44(17) . . ?
C11 C12 C13 121.63(19) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
C14 C13 C12 118.45(18) . . ?
C14 C13 C17 120.59(18) . . ?
C12 C13 C17 121.0(2) . . ?
C13 C14 C15 122.42(17) . . ?
C13 C14 H14A 118.8 . . ?
C15 C14 H14A 118.8 . . ?
C14 C15 C10 117.04(18) . . ?
C14 C15 C18 120.69(17) . . ?
C10 C15 C18 122.25(19) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C8 N1 N2 N3 0.9(2) . . . . ?
C19 N1 N2 N3 -178.9(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
N1 N2 N3 C9 -0.3(2) . . . . ?
N1 N2 N3 C10 173.58(15) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C7 N4 N5 C9 0.12(18) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 -179.09(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 178.77(17) . . . . ?
N5 N4 C7 C8 -0.76(19) . . . . ?
N5 N4 C7 C6 179.54(14) . . . . ?
C5 C6 C7 N4 152.49(17) . . . . ?
C1 C6 C7 N4 -25.9(2) . . . . ?
C5 C6 C7 C8 -27.1(3) . . . . ?
C1 C6 C7 C8 154.48(19) . . . . ?
N2 N1 C8 C9 -1.2(2) . . . . ?
C19 N1 C8 C9 178.6(2) . . . . ?
N2 N1 C8 C7 -174.6(3) . . . . ?
C19 N1 C8 C7 5.2(5) . . . . ?
N4 C7 C8 N1 174.5(3) . . . . ?
C6 C7 C8 N1 -5.9(5) . . . . ?
N4 C7 C8 C9 1.05(19) . . . . ?
C6 C7 C8 C9 -179.30(17) . . . . ?
N4 N5 C9 N3 -177.5(2) . . . . ?
N4 N5 C9 C8 0.62(19) . . . . ?
N2 N3 C9 N5 177.8(2) . . . . ?
C10 N3 C9 N5 4.6(3) . . . . ?
N2 N3 C9 C8 -0.43(19) . . . . ?
C10 N3 C9 C8 -173.60(16) . . . . ?
N1 C8 C9 N5 -177.80(15) . . . . ?
C7 C8 C9 N5 -1.1(2) . . . . ?
N1 C8 C9 N3 0.93(19) . . . . ?
C7 C8 C9 N3 177.67(14) . . . . ?
N2 N3 C10 C11 121.23(19) . . . . ?
C9 N3 C10 C11 -66.2(2) . . . . ?
N2 N3 C10 C15 -62.2(2) . . . . ?
C9 N3 C10 C15 110.3(2) . . . . ?
C15 C10 C11 C12 -1.5(3) . . . . ?
N3 C10 C11 C12 174.92(16) . . . . ?
C15 C10 C11 C16 177.64(17) . . . . ?
N3 C10 C11 C16 -6.0(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C16 C11 C12 C13 -178.98(18) . . . . ?
C11 C12 C13 C14 1.7(3) . . . . ?
C11 C12 C13 C17 -177.34(18) . . . . ?
C12 C13 C14 C15 -2.2(3) . . . . ?
C17 C13 C14 C15 176.77(18) . . . . ?
C13 C14 C15 C10 1.0(3) . . . . ?
C13 C14 C15 C18 -177.81(17) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
N3 C10 C15 C14 -175.43(16) . . . . ?
C11 C10 C15 C18 179.70(17) . . . . ?
N3 C10 C15 C18 3.3(3) . . . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_wl490
_database_code_depnum_ccdc_archive 'CCDC 2076290'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N3'
_chemical_formula_weight         353.45

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      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                   11.110(7)
_cell_length_b                   12.493(9)
_cell_length_c                   14.899(12)
_cell_angle_alpha                75.149(18)
_cell_angle_beta                 73.50(2)
_cell_angle_gamma                87.94(4)
_cell_volume                     1915(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8795
_cell_measurement_theta_min      1.913
_cell_measurement_theta_max      27.626

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_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  0.583718
_exptl_absorpt_correction_T_max  0.745556
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8795
_diffrn_reflns_av_unetI/netI     0.2662
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.913
_diffrn_reflns_theta_max         27.626
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8795
_reflns_number_gt                3711
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 3-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²] 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         8795
_refine_ls_number_parameters     495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2094
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.895
_refine_ls_shift/su_max          0.005
_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 -0.4615(3) 0.8730(2) 0.28067(19) 0.0295(7) Uani 1 1 d . . . . .
C1 C -0.1626(3) 0.6257(3) 0.2404(2) 0.0302(9) Uani 1 1 d . . . . .
H1 H -0.164587 0.657575 0.292224 0.036 Uiso 1 1 calc R U . . .
N2 N -0.5222(3) 0.8704(2) 0.3756(2) 0.0309(7) Uani 1 1 d . . . . .
C2 C -0.0916(3) 0.5340(3) 0.2302(3) 0.0357(10) Uani 1 1 d . . . . .
H2 H -0.047398 0.503045 0.276180 0.043 Uiso 1 1 calc R U . . .
N3 N -0.4679(3) 0.7869(2) 0.42235(19) 0.0276(7) Uani 1 1 d . . . . .
C3 C -0.0835(3) 0.4866(3) 0.1552(3) 0.0375(10) Uani 1 1 d . . . . .
H3 H -0.035507 0.422855 0.149665 0.045 Uiso 1 1 calc R U . . .
N4 N 0.1263(3) 0.7379(2) 0.2962(2) 0.0325(8) Uani 1 1 d . . . . .
C4 C -0.1465(3) 0.5336(3) 0.0879(2) 0.0363(10) Uani 1 1 d . . . . .
H4 H -0.139735 0.503408 0.034320 0.044 Uiso 1 1 calc R U . . .
N5 N 0.1090(3) 0.6936(2) 0.3938(2) 0.0358(8) Uani 1 1 d . . . . .
C5 C -0.2195(3) 0.6244(3) 0.0978(2) 0.0297(9) Uani 1 1 d . . . . .
H5 H -0.262257 0.655116 0.050778 0.036 Uiso 1 1 calc R U . . .
N6 N 0.0212(3) 0.7558(2) 0.4324(2) 0.0303(7) Uani 1 1 d . . . . .
C6 C -0.2321(3) 0.6724(3) 0.1752(2) 0.0264(9) Uani 1 1 d . . . . .
C7 C -0.3131(3) 0.7657(3) 0.1832(2) 0.0279(9) Uani 1 1 d . . . . .
H7 H -0.323706 0.813384 0.125302 0.033 Uiso 1 1 calc R U . . .
C8 C -0.3746(3) 0.7888(3) 0.2689(3) 0.0265(8) Uani 1 1 d . . . . .
C9 C -0.3813(3) 0.7376(3) 0.3659(2) 0.0284(9) Uani 1 1 d . . . . .
H9 H -0.332339 0.678014 0.387590 0.034 Uiso 1 1 calc R U . . .
C10 C -0.5000(3) 0.7604(3) 0.5265(2) 0.0259(8) Uani 1 1 d . . . . .
C11 C -0.5832(3) 0.6709(3) 0.5793(2) 0.0283(9) Uani 1 1 d . . . . .
C12 C -0.6037(3) 0.6414(3) 0.6791(2) 0.0323(9) Uani 1 1 d . . . . .
H12 H -0.660052 0.580805 0.717587 0.039 Uiso 1 1 calc R U . . .
C13 C -0.5442(3) 0.6981(3) 0.7235(2) 0.0279(9) Uani 1 1 d . . . . .
C14 C -0.4639(3) 0.7876(3) 0.6681(2) 0.0299(9) Uani 1 1 d . . . . .
H14 H -0.425074 0.827581 0.699462 0.036 Uiso 1 1 calc R U . . .
C15 C -0.4384(3) 0.8206(3) 0.5688(2) 0.0278(9) Uani 1 1 d . . . . .
C16 C -0.6491(3) 0.6084(3) 0.5318(2) 0.0406(10) Uani 1 1 d . . . . .
H16A H -0.693636 0.660355 0.492230 0.061 Uiso 1 1 calc R U . . .
H16B H -0.709402 0.553518 0.581688 0.061 Uiso 1 1 calc R U . . .
H16C H -0.587132 0.570570 0.490497 0.061 Uiso 1 1 calc R U . . .
C17 C -0.5641(3) 0.6628(3) 0.8314(2) 0.0394(10) Uani 1 1 d . . . . .
H17A H -0.486869 0.631992 0.844953 0.059 Uiso 1 1 calc R U . . .
H17B H -0.632696 0.606445 0.861118 0.059 Uiso 1 1 calc R U . . .
H17C H -0.585652 0.727166 0.858274 0.059 Uiso 1 1 calc R U . . .
C18 C -0.3481(3) 0.9158(3) 0.5104(2) 0.0431(10) Uani 1 1 d . . . . .
H18A H -0.334168 0.921786 0.441250 0.065 Uiso 1 1 calc R U . . .
H18B H -0.268158 0.903432 0.526254 0.065 Uiso 1 1 calc R U . . .
H18C H -0.382910 0.984482 0.525271 0.065 Uiso 1 1 calc R U . . .
C19 C -0.5004(3) 0.9538(3) 0.2085(2) 0.0292(9) Uani 1 1 d . . . . .
C20 C -0.4103(3) 1.0114(3) 0.1268(2) 0.0352(10) Uani 1 1 d . . . . .
H20 H -0.323826 0.996633 0.117867 0.042 Uiso 1 1 calc R U . . .
C21 C -0.4492(4) 1.0912(3) 0.0581(2) 0.0436(10) Uani 1 1 d . . . . .
H21 H -0.388741 1.131489 0.001356 0.052 Uiso 1 1 calc R U . . .
C22 C -0.5739(4) 1.1123(3) 0.0713(3) 0.0464(11) Uani 1 1 d . . . . .
H22 H -0.599213 1.167052 0.023557 0.056 Uiso 1 1 calc R U . . .
C23 C -0.6631(4) 1.0550(3) 0.1530(3) 0.0466(11) Uani 1 1 d . . . . .
H23 H -0.749290 1.071160 0.161873 0.056 Uiso 1 1 calc R U . . .
C24 C -0.6272(4) 0.9738(3) 0.2223(3) 0.0393(10) Uani 1 1 d . . . . .
H24 H -0.688289 0.932568 0.278112 0.047 Uiso 1 1 calc R U . . .
C25 C -0.1234(3) 1.0191(3) 0.2247(3) 0.0381(10) Uani 1 1 d . . . . .
H25 H -0.161341 0.966475 0.284022 0.046 Uiso 1 1 calc R U . . .
C26 C -0.1812(4) 1.1182(3) 0.2002(3) 0.0482(11) Uani 1 1 d . . . . .
H26 H -0.256601 1.133550 0.243727 0.058 Uiso 1 1 calc R U . . .
C27 C -0.1302(4) 1.1944(3) 0.1136(4) 0.0562(13) Uani 1 1 d . . . . .
H27 H -0.169132 1.262877 0.097730 0.067 Uiso 1 1 calc R U . . .
C28 C -0.0225(4) 1.1710(3) 0.0500(3) 0.0544(12) Uani 1 1 d . . . . .
H28 H 0.011792 1.222505 -0.010737 0.065 Uiso 1 1 calc R U . . .
C29 C 0.0354(4) 1.0742(3) 0.0737(2) 0.0408(9) Uani 1 1 d . . . . .
H29 H 0.109089 1.059566 0.028118 0.049 Uiso 1 1 calc R U . . .
C30 C -0.0095(3) 0.9947(3) 0.1633(3) 0.0314(9) Uani 1 1 d . . . . .
C31 C 0.0615(3) 0.8963(3) 0.1854(3) 0.0350(9) Uani 1 1 d . . . . .
H31 H 0.119241 0.876092 0.132321 0.042 Uiso 1 1 calc R U . . .
C32 C 0.0526(3) 0.8307(3) 0.2752(2) 0.0272(9) Uani 1 1 d . . . . .
C33 C -0.0178(3) 0.8363(3) 0.3693(3) 0.0325(9) Uani 1 1 d . . . . .
H33 H -0.080723 0.887407 0.384859 0.039 Uiso 1 1 calc R U . . .
C34 C -0.0298(3) 0.7312(3) 0.5362(2) 0.0262(8) Uani 1 1 d . . . . .
C35 C 0.0196(3) 0.7922(3) 0.5857(2) 0.0311(9) Uani 1 1 d . . . . .
C36 C -0.0363(3) 0.7721(3) 0.6844(2) 0.0307(9) Uani 1 1 d . . . . .
H36 H -0.005082 0.811543 0.720331 0.037 Uiso 1 1 calc R U . . .
C37 C -0.1361(3) 0.6963(3) 0.7325(2) 0.0262(9) Uani 1 1 d . . . . .
C38 C -0.1798(3) 0.6373(3) 0.6804(2) 0.0300(9) Uani 1 1 d . . . . .
H38 H -0.247501 0.584492 0.713461 0.036 Uiso 1 1 calc R U . . .
C39 C -0.1277(3) 0.6530(3) 0.5814(2) 0.0260(9) Uani 1 1 d . . . . .
C40 C 0.1274(3) 0.8753(3) 0.5354(3) 0.0465(11) Uani 1 1 d . . . . .
H40A H 0.191357 0.845184 0.488991 0.070 Uiso 1 1 calc R U . . .
H40B H 0.164055 0.891159 0.583428 0.070 Uiso 1 1 calc R U . . .
H40C H 0.097107 0.943815 0.501071 0.070 Uiso 1 1 calc R U . . .
C41 C -0.1964(3) 0.6788(3) 0.8392(2) 0.0352(9) Uani 1 1 d . . . . .
H41A H -0.279569 0.710615 0.850045 0.053 Uiso 1 1 calc R U . . .
H41B H -0.143851 0.715170 0.866538 0.053 Uiso 1 1 calc R U . . .
H41C H -0.204964 0.599241 0.870853 0.053 Uiso 1 1 calc R U . . .
C42 C -0.1784(3) 0.5883(3) 0.5277(2) 0.0419(10) Uani 1 1 d . . . . .
H42A H -0.270004 0.579989 0.553873 0.063 Uiso 1 1 calc R U . . .
H42B H -0.142240 0.514950 0.535256 0.063 Uiso 1 1 calc R U . . .
H42C H -0.156191 0.627547 0.458906 0.063 Uiso 1 1 calc R U . . .
C43 C 0.2217(3) 0.6924(3) 0.2312(2) 0.0302(9) Uani 1 1 d . . . . .
C44 C 0.1993(3) 0.6750(3) 0.1505(2) 0.0324(9) Uani 1 1 d . . . . .
H44 H 0.120809 0.692502 0.137752 0.039 Uiso 1 1 calc R U . . .
C45 C 0.2920(4) 0.6317(3) 0.0878(2) 0.0375(10) Uani 1 1 d . . . . .
H45 H 0.277657 0.620835 0.030845 0.045 Uiso 1 1 calc R U . . .
C46 C 0.4045(4) 0.6042(3) 0.1064(3) 0.0395(10) Uani 1 1 d . . . . .
H46 H 0.467376 0.573865 0.062794 0.047 Uiso 1 1 calc R U . . .
C47 C 0.4264(3) 0.6207(3) 0.1889(3) 0.0410(10) Uani 1 1 d . . . . .
H47 H 0.503849 0.600762 0.202567 0.049 Uiso 1 1 calc R U . . .
C48 C 0.3351(3) 0.6661(3) 0.2515(3) 0.0340(10) Uani 1 1 d . . . . .
H48 H 0.349897 0.679185 0.307570 0.041 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 N2 1.376(3) . ?
N1 C8 1.412(4) . ?
N1 C19 1.427(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.409(4) . ?
N2 N3 1.326(3) . ?
C2 C3 1.373(5) . ?
N3 C9 1.332(4) . ?
N3 C10 1.440(4) . ?
C3 C4 1.381(4) . ?
N4 N5 1.377(4) . ?
N4 C32 1.416(4) . ?
N4 C43 1.428(4) . ?
C4 C5 1.385(4) . ?
N5 N6 1.320(3) . ?
C5 C6 1.401(4) . ?
N6 C33 1.340(4) . ?
N6 C34 1.442(4) . ?
C6 C7 1.455(4) . ?
C7 C8 1.364(4) . ?
C8 C9 1.404(4) . ?
C10 C11 1.391(4) . ?
C10 C15 1.399(4) . ?
C11 C12 1.389(4) . ?
C11 C16 1.505(4) . ?
C12 C13 1.377(4) . ?
C13 C14 1.382(4) . ?
C13 C17 1.506(4) . ?
C14 C15 1.378(4) . ?
C15 C18 1.496(4) . ?
C19 C20 1.383(4) . ?
C19 C24 1.388(5) . ?
C20 C21 1.388(4) . ?
C21 C22 1.369(5) . ?
C22 C23 1.377(5) . ?
C23 C24 1.387(4) . ?
C25 C26 1.387(4) . ?
C25 C30 1.410(5) . ?
C26 C27 1.374(5) . ?
C27 C28 1.374(5) . ?
C28 C29 1.361(5) . ?
C29 C30 1.412(4) . ?
C30 C31 1.454(4) . ?
C31 C32 1.357(4) . ?
C32 C33 1.416(4) . ?
C34 C39 1.384(4) . ?
C34 C35 1.404(4) . ?
C35 C36 1.383(4) . ?
C35 C40 1.502(5) . ?
C36 C37 1.385(4) . ?
C37 C38 1.383(4) . ?
C37 C41 1.501(4) . ?
C38 C39 1.388(4) . ?
C39 C42 1.493(4) . ?
C43 C44 1.365(4) . ?
C43 C48 1.386(4) . ?
C44 C45 1.378(4) . ?
C45 C46 1.369(5) . ?
C46 C47 1.384(5) . ?
C47 C48 1.383(4) . ?

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 C8 114.2(3) . . ?
N2 N1 C19 116.6(3) . . ?
C8 N1 C19 129.0(3) . . ?
C2 C1 C6 120.9(3) . . ?
N3 N2 N1 101.5(2) . . ?
C3 C2 C1 121.7(3) . . ?
N2 N3 C9 115.0(3) . . ?
N2 N3 C10 119.4(3) . . ?
C9 N3 C10 125.4(3) . . ?
C2 C3 C4 118.5(3) . . ?
N5 N4 C32 113.4(3) . . ?
N5 N4 C43 117.2(3) . . ?
C32 N4 C43 129.1(3) . . ?
C3 C4 C5 120.5(3) . . ?
N6 N5 N4 102.1(3) . . ?
C4 C5 C6 122.0(3) . . ?
N5 N6 C33 115.7(3) . . ?
N5 N6 C34 119.6(3) . . ?
C33 N6 C34 124.6(3) . . ?
C5 C6 C1 116.3(3) . . ?
C5 C6 C7 119.4(3) . . ?
C1 C6 C7 124.3(3) . . ?
C8 C7 C6 123.9(3) . . ?
C7 C8 C9 133.4(3) . . ?
C7 C8 N1 125.7(3) . . ?
C9 C8 N1 100.7(3) . . ?
N3 C9 C8 108.4(3) . . ?
C11 C10 C15 123.4(3) . . ?
C11 C10 N3 118.3(3) . . ?
C15 C10 N3 118.2(3) . . ?
C12 C11 C10 116.8(3) . . ?
C12 C11 C16 121.0(3) . . ?
C10 C11 C16 122.2(3) . . ?
C13 C12 C11 121.6(3) . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 C17 121.0(3) . . ?
C14 C13 C17 119.5(3) . . ?
C15 C14 C13 121.9(3) . . ?
C14 C15 C10 116.7(3) . . ?
C14 C15 C18 120.8(3) . . ?
C10 C15 C18 122.5(3) . . ?
C20 C19 C24 121.5(3) . . ?
C20 C19 N1 119.0(3) . . ?
C24 C19 N1 119.5(3) . . ?
C19 C20 C21 118.5(4) . . ?
C22 C21 C20 120.6(4) . . ?
C21 C22 C23 120.7(3) . . ?
C22 C23 C24 120.0(4) . . ?
C23 C24 C19 118.7(4) . . ?
C26 C25 C30 121.4(4) . . ?
C27 C26 C25 120.5(4) . . ?
C26 C27 C28 119.6(4) . . ?
C29 C28 C27 120.3(4) . . ?
C28 C29 C30 122.8(4) . . ?
C25 C30 C29 115.3(3) . . ?
C25 C30 C31 125.3(3) . . ?
C29 C30 C31 119.4(3) . . ?
C32 C31 C30 125.7(3) . . ?
C31 C32 N4 125.1(3) . . ?
C31 C32 C33 133.1(3) . . ?
N4 C32 C33 101.6(3) . . ?
N6 C33 C32 107.1(3) . . ?
C39 C34 C35 123.3(3) . . ?
C39 C34 N6 118.8(3) . . ?
C35 C34 N6 117.7(3) . . ?
C36 C35 C34 116.6(3) . . ?
C36 C35 C40 120.9(3) . . ?
C34 C35 C40 122.5(3) . . ?
C35 C36 C37 122.1(3) . . ?
C38 C37 C36 118.9(3) . . ?
C38 C37 C41 120.6(3) . . ?
C36 C37 C41 120.6(3) . . ?
C37 C38 C39 121.9(3) . . ?
C34 C39 C38 117.1(3) . . ?
C34 C39 C42 122.7(3) . . ?
C38 C39 C42 120.2(3) . . ?
C44 C43 C48 121.2(3) . . ?
C44 C43 N4 119.3(3) . . ?
C48 C43 N4 119.5(3) . . ?
C43 C44 C45 119.0(4) . . ?
C46 C45 C44 121.0(4) . . ?
C45 C46 C47 119.8(4) . . ?
C48 C47 C46 119.8(4) . . ?
C47 C48 C43 119.1(3) . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_wl489a
_database_code_depnum_ccdc_archive 'CCDC 2076291'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 N3 O'
_chemical_formula_weight         335.44

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'
O O 0.0106 0.0060 '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                   8.327(7)
_cell_length_b                   14.460(10)
_cell_length_c                   29.68(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.26(3)
_cell_angle_gamma                90
_cell_volume                     3568(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    58380
_cell_measurement_theta_min      1.567
_cell_measurement_theta_max      25.332

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58380
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_av_R_equivalents  0.1689
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.567
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6455
_reflns_number_gt                3804
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0899P)²+15.7023P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0137(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6455
_refine_ls_number_parameters     456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1933
_refine_ls_R_factor_gt           0.1096
_refine_ls_wR_factor_ref         0.2983
_refine_ls_wR_factor_gt          0.2428
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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
O1 O 0.4981(5) 0.7795(3) 0.09815(13) 0.0302(10) Uani 1 1 d . . . . .
N1 N 0.9018(6) 0.7253(3) 0.32840(16) 0.0287(11) Uani 1 1 d . . . . .
C1 C 1.3416(7) 0.5909(4) 0.2786(2) 0.0343(15) Uani 1 1 d . . . . .
H1 H 1.257582 0.596414 0.255760 0.041 Uiso 1 1 calc R U . . .
O2 O 0.8978(5) 0.8034(3) 0.06175(14) 0.0359(11) Uani 1 1 d . . . . .
N2 N 0.7841(6) 0.7486(3) 0.29765(15) 0.0281(11) Uani 1 1 d . . . . .
C2 C 1.4892(7) 0.5590(4) 0.2672(2) 0.0353(15) Uani 1 1 d . . . . .
H2 H 1.505927 0.543407 0.236719 0.042 Uiso 1 1 calc R U . . .
N3 N 0.8380(5) 0.7164(3) 0.26039(15) 0.0251(11) Uani 1 1 d . . . . .
C3 C 1.6141(8) 0.5493(4) 0.2999(2) 0.0411(17) Uani 1 1 d . . . . .
H3 H 1.716676 0.528172 0.291920 0.049 Uiso 1 1 calc R U . . .
N4 N 1.2797(6) 0.8693(3) 0.29520(16) 0.0289(11) Uani 1 1 d . . . . .
C4 C 1.5876(8) 0.5707(4) 0.3439(2) 0.0364(16) Uani 1 1 d . . . . .
H4 H 1.671899 0.563448 0.366557 0.044 Uiso 1 1 calc R U . . .
N5 N 1.2769(6) 0.8438(3) 0.25166(17) 0.0308(12) Uani 1 1 d . . . . .
C5 C 1.4401(7) 0.6025(4) 0.3553(2) 0.0327(14) Uani 1 1 d . . . . .
H5 H 1.424782 0.616137 0.386096 0.039 Uiso 1 1 calc R U . . .
N6 N 1.1359(6) 0.8727(3) 0.23580(15) 0.0267(11) Uani 1 1 d . . . . .
C6 C 1.3107(7) 0.6157(4) 0.3235(2) 0.0286(13) Uani 1 1 d . . . . .
C7 C 1.1644(7) 0.6534(4) 0.3377(2) 0.0281(13) Uani 1 1 d . . . . .
H7 H 1.157597 0.661723 0.369278 0.034 Uiso 1 1 calc R U . . .
C8 C 1.0310(7) 0.6794(4) 0.31091(19) 0.0257(13) Uani 1 1 d . . . . .
C9 C 0.9810(7) 0.6739(4) 0.2651(2) 0.0268(13) Uani 1 1 d . . . . .
H9 H 1.037479 0.645470 0.241816 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7442(7) 0.7311(4) 0.21942(19) 0.0255(13) Uani 1 1 d . . . . .
C11 C 0.6518(7) 0.8102(4) 0.21508(19) 0.0274(13) Uani 1 1 d . . . . .
H11 H 0.648248 0.852505 0.239500 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5649(7) 0.8274(4) 0.17519(19) 0.0276(13) Uani 1 1 d . . . . .
H12 H 0.499251 0.880965 0.172052 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5738(7) 0.7663(4) 0.13975(19) 0.0279(13) Uani 1 1 d . . . . .
C14 C 0.6643(7) 0.6863(4) 0.14421(19) 0.0278(13) Uani 1 1 d . . . . .
H14 H 0.667026 0.643646 0.119900 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7506(7) 0.6691(4) 0.1845(2) 0.0279(13) Uani 1 1 d . . . . .
H15 H 0.814087 0.614686 0.187976 0.033 Uiso 1 1 calc R U . . .
C16 C 0.4331(7) 0.8697(4) 0.0896(2) 0.0318(14) Uani 1 1 d . . . . .
H16A H 0.516629 0.917262 0.096302 0.038 Uiso 1 1 calc R U . . .
H16B H 0.342496 0.881222 0.109040 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3760(8) 0.8746(4) 0.0411(2) 0.0337(14) Uani 1 1 d . . . . .
H17A H 0.300330 0.823073 0.034042 0.040 Uiso 1 1 calc R U . . .
H17B H 0.468817 0.867439 0.021947 0.040 Uiso 1 1 calc R U . . .
C18 C 0.2921(8) 0.9664(4) 0.0302(2) 0.0367(15) Uani 1 1 d . . . . .
H18A H 0.195938 0.971284 0.048150 0.044 Uiso 1 1 calc R U . . .
H18B H 0.365759 1.017556 0.039503 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2408(8) 0.9785(4) -0.0191(2) 0.0360(15) Uani 1 1 d . . . . .
H19A H 0.194003 1.041036 -0.023655 0.043 Uiso 1 1 calc R U . . .
H19B H 0.336943 0.974525 -0.037187 0.043 Uiso 1 1 calc R U . . .
C20 C 0.1194(8) 0.9076(5) -0.0363(2) 0.0409(16) Uani 1 1 d . . . . .
H20A H 0.076771 0.925269 -0.066576 0.061 Uiso 1 1 calc R U . . .
H20B H 0.031156 0.904509 -0.015906 0.061 Uiso 1 1 calc R U . . .
H20C H 0.171420 0.846956 -0.037698 0.061 Uiso 1 1 calc R U . . .
C21 C 0.8829(8) 0.7478(4) 0.37523(19) 0.0351(15) Uani 1 1 d . . . . .
H21A H 0.783102 0.782740 0.377902 0.053 Uiso 1 1 calc R U . . .
H21B H 0.974466 0.785233 0.386696 0.053 Uiso 1 1 calc R U . . .
H21C H 0.878432 0.690619 0.392846 0.053 Uiso 1 1 calc R U . . .
C22 C 0.8407(7) 1.0079(4) 0.3434(2) 0.0315(14) Uani 1 1 d . . . . .
H22 H 0.838480 1.002913 0.311458 0.038 Uiso 1 1 calc R U . . .
C23 C 0.7085(8) 1.0427(4) 0.3629(2) 0.0393(16) Uani 1 1 d . . . . .
H23 H 0.617879 1.062065 0.344418 0.047 Uiso 1 1 calc R U . . .
C24 C 0.7055(8) 1.0498(4) 0.4089(2) 0.0415(17) Uani 1 1 d . . . . .
H24 H 0.612946 1.073272 0.422329 0.050 Uiso 1 1 calc R U . . .
C25 C 0.8396(8) 1.0223(4) 0.4356(2) 0.0384(16) Uani 1 1 d . . . . .
H25 H 0.839351 1.026559 0.467565 0.046 Uiso 1 1 calc R U . . .
C26 C 0.9707(8) 0.9895(4) 0.4158(2) 0.0352(15) Uani 1 1 d . . . . .
H26 H 1.061657 0.972384 0.434697 0.042 Uiso 1 1 calc R U . . .
C27 C 0.9804(7) 0.9790(4) 0.36886(19) 0.0283(13) Uani 1 1 d . . . . .
C28 C 1.1195(7) 0.9409(4) 0.35118(19) 0.0274(13) Uani 1 1 d . . . . .
H28 H 1.209939 0.933833 0.371879 0.033 Uiso 1 1 calc R U . . .
C29 C 1.1401(7) 0.9128(4) 0.30759(19) 0.0256(13) Uani 1 1 d . . . . .
C30 C 1.0482(7) 0.9153(4) 0.26666(19) 0.0267(13) Uani 1 1 d . . . . .
H30 H 0.944389 0.941811 0.261549 0.032 Uiso 1 1 calc R U . . .
C31 C 1.0867(7) 0.8565(4) 0.1896(2) 0.0274(13) Uani 1 1 d . . . . .
C32 C 0.9794(7) 0.9166(4) 0.1682(2) 0.0287(13) Uani 1 1 d . . . . .
H32 H 0.946875 0.971228 0.182971 0.034 Uiso 1 1 calc R U . . .
C33 C 0.9200(7) 0.8969(4) 0.1253(2) 0.0324(14) Uani 1 1 d . . . . .
H33 H 0.844338 0.937375 0.110426 0.039 Uiso 1 1 calc R U . . .
C34 C 0.9700(7) 0.8178(4) 0.10341(19) 0.0288(13) Uani 1 1 d . . . . .
C35 C 1.0821(7) 0.7597(4) 0.1247(2) 0.0292(14) Uani 1 1 d . . . . .
H35 H 1.118241 0.706407 0.109555 0.035 Uiso 1 1 calc R U . . .
C36 C 1.1415(7) 0.7793(4) 0.1679(2) 0.0279(13) Uani 1 1 d . . . . .
H36 H 1.219405 0.740000 0.182619 0.033 Uiso 1 1 calc R U . . .
C37 C 0.9441(8) 0.7213(4) 0.0377(2) 0.0373(15) Uani 1 1 d . . . . .
H37A H 0.930134 0.665557 0.056451 0.045 Uiso 1 1 calc R U . . .
H37B H 1.058271 0.725339 0.030259 0.045 Uiso 1 1 calc R U . . .
C38 C 0.8373(8) 0.7162(5) -0.0046(2) 0.0382(16) Uani 1 1 d . . . . .
H38A H 0.888136 0.675276 -0.026439 0.046 Uiso 1 1 calc R U . . .
H38B H 0.828376 0.778638 -0.018165 0.046 Uiso 1 1 calc R U . . .
C39 C 0.6683(8) 0.6800(4) 0.0029(2) 0.0371(15) Uani 1 1 d . . . . .
H39A H 0.676046 0.614891 0.013028 0.045 Uiso 1 1 calc R U . . .
H39B H 0.621957 0.716423 0.027238 0.045 Uiso 1 1 calc R U . . .
C40 C 0.5557(8) 0.6853(5) -0.0391(2) 0.0439(17) Uani 1 1 d . . . . .
H40A H 0.541410 0.750903 -0.048023 0.053 Uiso 1 1 calc R U . . .
H40B H 0.605063 0.652496 -0.064086 0.053 Uiso 1 1 calc R U . . .
C41 C 0.3934(9) 0.6434(5) -0.0318(3) 0.055(2) Uani 1 1 d . . . . .
H41A H 0.322436 0.652225 -0.058934 0.083 Uiso 1 1 calc R U . . .
H41B H 0.346407 0.673620 -0.006076 0.083 Uiso 1 1 calc R U . . .
H41C H 0.405904 0.577138 -0.025623 0.083 Uiso 1 1 calc R U . . .
C42 C 1.4156(7) 0.8456(4) 0.3247(2) 0.0328(14) Uani 1 1 d . . . . .
H42A H 1.491817 0.808996 0.308129 0.049 Uiso 1 1 calc R U . . .
H42B H 1.379598 0.809286 0.350146 0.049 Uiso 1 1 calc R U . . .
H42C H 1.468431 0.902193 0.336090 0.049 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
O1 C13 1.367(7) . ?
O1 C16 1.429(7) . ?
N1 N2 1.344(6) . ?
N1 C8 1.389(7) . ?
N1 C21 1.445(7) . ?
C1 C2 1.373(9) . ?
C1 C6 1.416(9) . ?
O2 C34 1.360(7) . ?
O2 C37 1.449(7) . ?
N2 N3 1.303(6) . ?
C2 C3 1.389(9) . ?
N3 C9 1.340(7) . ?
N3 C10 1.423(7) . ?
C3 C4 1.371(9) . ?
N4 N5 1.343(7) . ?
N4 C29 1.389(7) . ?
N4 C42 1.433(7) . ?
C4 C5 1.372(9) . ?
N5 N6 1.308(7) . ?
C5 C6 1.405(8) . ?
N6 C30 1.352(7) . ?
N6 C31 1.427(7) . ?
C6 C7 1.420(8) . ?
C7 C8 1.381(8) . ?
C8 C9 1.403(8) . ?
C10 C15 1.375(8) . ?
C10 C11 1.381(8) . ?
C11 C12 1.374(8) . ?
C12 C13 1.379(8) . ?
C13 C14 1.383(8) . ?
C14 C15 1.381(8) . ?
C16 C17 1.492(8) . ?
C17 C18 1.527(8) . ?
C18 C19 1.511(8) . ?
C19 C20 1.508(9) . ?
C22 C23 1.369(9) . ?
C22 C27 1.413(8) . ?
C23 C24 1.369(9) . ?
C24 C25 1.391(9) . ?
C25 C26 1.356(9) . ?
C26 C27 1.407(8) . ?
C27 C28 1.411(8) . ?
C28 C29 1.376(8) . ?
C29 C30 1.399(8) . ?
C31 C32 1.377(8) . ?
C31 C36 1.380(8) . ?
C32 C33 1.369(8) . ?
C33 C34 1.391(8) . ?
C34 C35 1.381(8) . ?
C35 C36 1.377(8) . ?
C37 C38 1.499(8) . ?
C38 C39 1.529(9) . ?
C39 C40 1.517(9) . ?
C40 C41 1.508(10) . ?

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
C13 O1 C16 116.1(4) . . ?
N2 N1 C8 114.6(5) . . ?
N2 N1 C21 118.8(5) . . ?
C8 N1 C21 126.6(5) . . ?
C2 C1 C6 122.0(6) . . ?
C34 O2 C37 117.2(4) . . ?
N3 N2 N1 102.4(4) . . ?
C1 C2 C3 120.4(6) . . ?
N2 N3 C9 115.0(5) . . ?
N2 N3 C10 118.2(5) . . ?
C9 N3 C10 126.7(5) . . ?
C4 C3 C2 119.2(6) . . ?
N5 N4 C29 114.2(5) . . ?
N5 N4 C42 119.5(5) . . ?
C29 N4 C42 126.2(5) . . ?
C3 C4 C5 120.4(6) . . ?
N6 N5 N4 103.0(4) . . ?
C4 C5 C6 122.8(6) . . ?
N5 N6 C30 114.2(5) . . ?
N5 N6 C31 119.7(5) . . ?
C30 N6 C31 126.1(5) . . ?
C5 C6 C1 115.1(6) . . ?
C5 C6 C7 119.3(6) . . ?
C1 C6 C7 125.5(5) . . ?
C8 C7 C6 127.5(6) . . ?
C7 C8 N1 122.0(5) . . ?
C7 C8 C9 136.7(6) . . ?
N1 C8 C9 101.3(5) . . ?
N3 C9 C8 106.7(5) . . ?
C15 C10 C11 121.0(5) . . ?
C15 C10 N3 120.3(5) . . ?
C11 C10 N3 118.6(5) . . ?
C12 C11 C10 119.5(5) . . ?
C11 C12 C13 119.5(5) . . ?
O1 C13 C12 123.8(5) . . ?
O1 C13 C14 115.1(5) . . ?
C12 C13 C14 121.0(5) . . ?
C15 C14 C13 119.1(5) . . ?
C10 C15 C14 119.7(5) . . ?
O1 C16 C17 108.1(5) . . ?
C16 C17 C18 111.3(5) . . ?
C19 C18 C17 114.0(5) . . ?
C20 C19 C18 113.3(5) . . ?
C23 C22 C27 122.6(6) . . ?
C22 C23 C24 120.7(6) . . ?
C23 C24 C25 119.1(6) . . ?
C26 C25 C24 119.5(6) . . ?
C25 C26 C27 124.1(6) . . ?
C26 C27 C28 120.3(6) . . ?
C26 C27 C22 113.9(6) . . ?
C28 C27 C22 125.8(5) . . ?
C29 C28 C27 127.9(6) . . ?
C28 C29 N4 122.3(5) . . ?
C28 C29 C30 135.8(6) . . ?
N4 C29 C30 101.9(5) . . ?
N6 C30 C29 106.7(5) . . ?
C32 C31 C36 121.2(6) . . ?
C32 C31 N6 118.9(5) . . ?
C36 C31 N6 119.8(5) . . ?
C33 C32 C31 119.3(5) . . ?
C32 C33 C34 120.2(5) . . ?
O2 C34 C35 125.1(5) . . ?
O2 C34 C33 114.9(5) . . ?
C35 C34 C33 119.9(5) . . ?
C36 C35 C34 119.9(5) . . ?
C35 C36 C31 119.4(5) . . ?
O2 C37 C38 107.0(5) . . ?
C37 C38 C39 113.7(5) . . ?
C40 C39 C38 113.2(5) . . ?
C41 C40 C39 112.3(6) . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.114



####################################################################### 
# 
# 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_wl478
_database_code_depnum_ccdc_archive 'CCDC 2076288'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 N3'
_chemical_formula_weight         305.41

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.944(4)
_cell_length_b                   9.040(4)
_cell_length_c                   14.465(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.393(12)
_cell_angle_gamma                90
_cell_volume                     1664.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18766
_cell_measurement_theta_min      3.644
_cell_measurement_theta_max      32.342

_exptl_crystal_description       block
_exptl_crystal_colour            'dark blue purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18766
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.644
_diffrn_reflns_theta_max         32.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5210
_reflns_number_gt                3647
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0849P)²] 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         5210
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.01293(6) 0.27182(11) 0.43005(6) 0.0291(2) Uani 1 1 d . . . . .
C1 C 0.03110(8) 0.73953(14) 0.33158(8) 0.0342(3) Uani 1 1 d . . . . .
H1 H 0.091444 0.709179 0.374978 0.041 Uiso 1 1 calc R U . . .
N2 N 0.10324(7) 0.20680(11) 0.47235(6) 0.0296(2) Uani 1 1 d . . . . .
C2 C 0.03073(9) 0.87758(14) 0.29111(9) 0.0399(3) Uani 1 1 d . . . . .
H2 H 0.090434 0.939784 0.307140 0.048 Uiso 1 1 calc R U . . .
N3 N 0.17338(6) 0.31114(10) 0.46814(6) 0.0253(2) Uani 1 1 d . . . . .
C3 C -0.05546(9) 0.92717(14) 0.22734(8) 0.0376(3) Uani 1 1 d . . . . .
H3 H -0.055450 1.022006 0.199054 0.045 Uiso 1 1 calc R U . . .
C4 C -0.14157(9) 0.83408(14) 0.20617(8) 0.0353(3) Uani 1 1 d . . . . .
H4 H -0.201588 0.866155 0.162998 0.042 Uiso 1 1 calc R U . . .
C5 C -0.14195(8) 0.69615(14) 0.24637(8) 0.0320(3) Uani 1 1 d . . . . .
H5 H -0.202519 0.635598 0.230339 0.038 Uiso 1 1 calc R U . . .
C6 C -0.05479(7) 0.64168(12) 0.31091(7) 0.0269(2) Uani 1 1 d . . . . .
C7 C -0.05855(7) 0.49605(12) 0.34882(7) 0.0283(2) Uani 1 1 d . . . . .
H7 H -0.125595 0.449975 0.339433 0.034 Uiso 1 1 calc R U . . .
C8 C 0.02434(7) 0.41432(12) 0.39767(7) 0.0259(2) Uani 1 1 d . . . . .
C9 C 0.13378(7) 0.43672(12) 0.42547(7) 0.0259(2) Uani 1 1 d . . . . .
H9 H 0.171946 0.523447 0.415906 0.031 Uiso 1 1 calc R U . . .
C10 C 0.28140(8) 0.28115(12) 0.50670(7) 0.0246(2) Uani 1 1 d . . . . .
C11 C 0.35910(8) 0.33772(12) 0.46234(8) 0.0292(2) Uani 1 1 d . . . . .
H11 H 0.341094 0.397651 0.407863 0.035 Uiso 1 1 calc R U . . .
C12 C 0.46329(8) 0.30606(12) 0.49815(8) 0.0286(2) Uani 1 1 d . . . . .
H12 H 0.516426 0.346102 0.467997 0.034 Uiso 1 1 calc R U . . .
C13 C 0.49230(7) 0.21714(11) 0.57714(7) 0.0236(2) Uani 1 1 d . . . . .
C14 C 0.41155(8) 0.16311(13) 0.62041(7) 0.0293(2) Uani 1 1 d . . . . .
H14 H 0.428971 0.102974 0.674854 0.035 Uiso 1 1 calc R U . . .
C15 C 0.30703(8) 0.19480(13) 0.58616(7) 0.0298(2) Uani 1 1 d . . . . .
H15 H 0.253583 0.157525 0.617008 0.036 Uiso 1 1 calc R U . . .
C16 C 0.60712(7) 0.17901(12) 0.61677(7) 0.0255(2) Uani 1 1 d . . . . .
C17 C 0.61736(9) 0.01882(13) 0.65060(9) 0.0376(3) Uani 1 1 d . . . . .
H17A H 0.587150 -0.047140 0.598996 0.056 Uiso 1 1 calc R U . . .
H17B H 0.579773 0.006086 0.703120 0.056 Uiso 1 1 calc R U . . .
H17C H 0.691736 -0.005320 0.671409 0.056 Uiso 1 1 calc R U . . .
C18 C 0.64710(9) 0.28126(13) 0.70019(8) 0.0344(3) Uani 1 1 d . . . . .
H18A H 0.641044 0.384476 0.679201 0.052 Uiso 1 1 calc R U . . .
H18B H 0.720835 0.258478 0.725357 0.052 Uiso 1 1 calc R U . . .
H18C H 0.604974 0.266154 0.749298 0.052 Uiso 1 1 calc R U . . .
C19 C 0.67590(8) 0.19895(15) 0.54160(8) 0.0371(3) Uani 1 1 d . . . . .
H19A H 0.647435 0.139337 0.486269 0.056 Uiso 1 1 calc R U . . .
H19B H 0.747746 0.166791 0.566889 0.056 Uiso 1 1 calc R U . . .
H19C H 0.676421 0.303441 0.523665 0.056 Uiso 1 1 calc R U . . .
C20 C -0.08347(9) 0.18778(14) 0.41821(9) 0.0389(3) Uani 1 1 d . . . . .
H20A H -0.108654 0.169228 0.351185 0.058 Uiso 1 1 calc R U . . .
H20B H -0.136592 0.243816 0.443949 0.058 Uiso 1 1 calc R U . . .
H20C H -0.070567 0.093263 0.451472 0.058 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 N2 1.3522(13) . ?
N1 C8 1.3878(15) . ?
N1 C20 1.4444(14) . ?
C1 C2 1.3781(18) . ?
C1 C6 1.4100(15) . ?
C1 H1 0.9500 . ?
N2 N3 1.3183(12) . ?
C2 C3 1.3875(16) . ?
C2 H2 0.9500 . ?
N3 C9 1.3485(14) . ?
N3 C10 1.4346(13) . ?
C3 C4 1.3861(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3762(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4166(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4304(16) . ?
C7 C8 1.3866(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4155(14) . ?
C9 H9 0.9500 . ?
C10 C15 1.3796(15) . ?
C10 C11 1.3848(14) . ?
C11 C12 1.3845(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3922(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3995(14) . ?
C13 C16 1.5326(14) . ?
C14 C15 1.3842(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.5267(16) . ?
C16 C18 1.5339(15) . ?
C16 C19 1.5351(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 C8 114.85(8) . . ?
N2 N1 C20 118.87(10) . . ?
C8 N1 C20 126.20(9) . . ?
C2 C1 C6 122.41(10) . . ?
C2 C1 H1 118.8 . . ?
C6 C1 H1 118.8 . . ?
N3 N2 N1 102.38(9) . . ?
C1 C2 C3 121.05(11) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
N2 N3 C9 114.55(9) . . ?
N2 N3 C10 118.54(9) . . ?
C9 N3 C10 126.90(9) . . ?
C4 C3 C2 117.96(12) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C5 C4 C3 121.38(10) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 122.03(11) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 115.17(11) . . ?
C1 C6 C7 125.19(9) . . ?
C5 C6 C7 119.64(10) . . ?
C8 C7 C6 127.52(10) . . ?
C8 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
C7 C8 N1 123.16(9) . . ?
C7 C8 C9 135.33(10) . . ?
N1 C8 C9 101.48(9) . . ?
N3 C9 C8 106.73(9) . . ?
N3 C9 H9 126.6 . . ?
C8 C9 H9 126.6 . . ?
C15 C10 C11 120.63(9) . . ?
C15 C10 N3 120.12(9) . . ?
C11 C10 N3 119.24(9) . . ?
C10 C11 C12 119.35(10) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 121.78(9) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 117.13(9) . . ?
C12 C13 C16 122.45(9) . . ?
C14 C13 C16 120.42(9) . . ?
C15 C14 C13 121.89(10) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C10 C15 C14 119.20(9) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C13 110.83(8) . . ?
C17 C16 C18 108.79(9) . . ?
C13 C16 C18 108.99(9) . . ?
C17 C16 C19 108.09(9) . . ?
C13 C16 C19 110.84(9) . . ?
C18 C16 C19 109.26(9) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C8 N1 N2 N3 1.00(11) . . . . ?
C20 N1 N2 N3 177.93(10) . . . . ?
C6 C1 C2 C3 0.02(19) . . . . ?
N1 N2 N3 C9 -0.56(11) . . . . ?
N1 N2 N3 C10 -179.63(8) . . . . ?
C1 C2 C3 C4 0.54(18) . . . . ?
C2 C3 C4 C5 -0.43(18) . . . . ?
C3 C4 C5 C6 -0.26(18) . . . . ?
C2 C1 C6 C5 -0.67(17) . . . . ?
C2 C1 C6 C7 178.58(11) . . . . ?
C4 C5 C6 C1 0.79(16) . . . . ?
C4 C5 C6 C7 -178.51(10) . . . . ?
C1 C6 C7 C8 -12.52(17) . . . . ?
C5 C6 C7 C8 166.70(10) . . . . ?
C6 C7 C8 N1 -178.58(9) . . . . ?
C6 C7 C8 C9 -1.29(19) . . . . ?
N2 N1 C8 C7 177.03(9) . . . . ?
C20 N1 C8 C7 0.36(17) . . . . ?
N2 N1 C8 C9 -1.02(11) . . . . ?
C20 N1 C8 C9 -177.69(10) . . . . ?
N2 N3 C9 C8 -0.04(12) . . . . ?
C10 N3 C9 C8 178.94(9) . . . . ?
C7 C8 C9 N3 -177.08(11) . . . . ?
N1 C8 C9 N3 0.60(10) . . . . ?
N2 N3 C10 C15 -35.43(14) . . . . ?
C9 N3 C10 C15 145.63(11) . . . . ?
N2 N3 C10 C11 143.49(10) . . . . ?
C9 N3 C10 C11 -35.46(15) . . . . ?
C15 C10 C11 C12 0.40(17) . . . . ?
N3 C10 C11 C12 -178.50(9) . . . . ?
C10 C11 C12 C13 0.80(17) . . . . ?
C11 C12 C13 C14 -1.30(17) . . . . ?
C11 C12 C13 C16 179.01(10) . . . . ?
C12 C13 C14 C15 0.65(17) . . . . ?
C16 C13 C14 C15 -179.66(10) . . . . ?
C11 C10 C15 C14 -1.04(17) . . . . ?
N3 C10 C15 C14 177.86(10) . . . . ?
C13 C14 C15 C10 0.50(18) . . . . ?
C12 C13 C16 C17 -141.24(11) . . . . ?
C14 C13 C16 C17 39.08(14) . . . . ?
C12 C13 C16 C18 99.07(12) . . . . ?
C14 C13 C16 C18 -80.61(13) . . . . ?
C12 C13 C16 C19 -21.22(14) . . . . ?
C14 C13 C16 C19 159.10(10) . . . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_wl461a
_database_code_depnum_ccdc_archive 'CCDC 2076296'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.48

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   22.126(7)
_cell_length_b                   22.131(6)
_cell_length_c                   17.067(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.565(13)
_cell_angle_gamma                90
_cell_volume                     8354(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    91833
_cell_measurement_theta_min      1.302
_cell_measurement_theta_max      27.588

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             3136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_T_max  0.7409
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            91833
_diffrn_reflns_av_unetI/netI     0.1053
_diffrn_reflns_av_R_equivalents  0.1243
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.302
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9621
_reflns_number_gt                5312
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0886P)²+13.3408P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9621
_refine_ls_number_parameters     512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0840
_refine_ls_wR_factor_ref         0.2441
_refine_ls_wR_factor_gt          0.2117
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.58255(11) 0.03507(12) 0.19671(14) 0.0426(6) Uani 1 1 d . . . . .
C1 C 0.61406(16) -0.08658(16) 0.40503(18) 0.0498(8) Uani 1 1 d . . . . .
H1A H 0.625409 -0.045870 0.415223 0.060 Uiso 1 1 calc R U . . .
N2 N 0.60767(12) 0.09131(12) 0.20070(15) 0.0445(7) Uani 1 1 d . . . . .
C2 C 0.62271(19) -0.12908(18) 0.4627(2) 0.0631(10) Uani 1 1 d . . . . .
H2A H 0.639261 -0.117149 0.512308 0.076 Uiso 1 1 calc R U . . .
C3 C 0.6077(2) -0.18914(19) 0.4500(2) 0.0712(12) Uani 1 1 d . . . . .
H3A H 0.614775 -0.218497 0.489767 0.085 Uiso 1 1 calc R U . . .
N3 N 0.63382(11) 0.09128(11) 0.27072(14) 0.0403(6) Uani 1 1 d . . . . .
N4 N 0.58188(11) 0.47668(11) 0.29798(13) 0.0357(6) Uani 1 1 d . . . . .
C4 C 0.58225(19) -0.20553(18) 0.3783(2) 0.0659(11) Uani 1 1 d . . . . .
H4A H 0.571078 -0.246420 0.369060 0.079 Uiso 1 1 calc R U . . .
N5 N 0.60557(11) 0.42018(11) 0.29558(14) 0.0375(6) Uani 1 1 d . . . . .
C5 C 0.57299(16) -0.16358(17) 0.3205(2) 0.0548(9) Uani 1 1 d . . . . .
H5A H 0.555434 -0.176106 0.271751 0.066 Uiso 1 1 calc R U . . .
C6 C 0.58875(14) -0.10184(15) 0.33095(18) 0.0446(8) Uani 1 1 d . . . . .
N6 N 0.62829(11) 0.41834(11) 0.22525(13) 0.0353(6) Uani 1 1 d . . . . .
C7 C 0.57769(14) -0.06069(15) 0.26706(18) 0.0439(8) Uani 1 1 d . . . . .
H7A H 0.555536 -0.076399 0.223155 0.053 Uiso 1 1 calc R U . . .
C8 C 0.59532(13) -0.00132(15) 0.26189(17) 0.0401(7) Uani 1 1 d . . . . .
C9 C 0.62827(13) 0.03937(14) 0.31093(17) 0.0390(7) Uani 1 1 d . . . . .
H9A H 0.643541 0.031471 0.362482 0.047 Uiso 1 1 calc R U . . .
C10 C 0.66612(15) 0.14381(14) 0.29865(18) 0.0422(7) Uani 1 1 d . . . . .
C11 C 0.72853(15) 0.14076(14) 0.3063(2) 0.0484(8) Uani 1 1 d . . . . .
C12 C 0.75853(17) 0.19009(15) 0.3395(2) 0.0570(9) Uani 1 1 d . . . . .
H12A H 0.801253 0.188672 0.346415 0.068 Uiso 1 1 calc R U . . .
C13 C 0.7278(2) 0.24104(15) 0.3626(2) 0.0600(10) Uani 1 1 d . . . . .
C14 C 0.6652(2) 0.24261(15) 0.35206(19) 0.0578(10) Uani 1 1 d . . . . .
H14A H 0.643958 0.277885 0.367037 0.069 Uiso 1 1 calc R U . . .
C15 C 0.63307(16) 0.19468(15) 0.32058(18) 0.0498(9) Uani 1 1 d . . . . .
C16 C 0.76379(16) 0.08659(16) 0.2795(3) 0.0663(11) Uani 1 1 d . . . . .
H16A H 0.804533 0.099269 0.265469 0.099 Uiso 1 1 calc R U . . .
H16B H 0.743178 0.068495 0.233667 0.099 Uiso 1 1 calc R U . . .
H16C H 0.766569 0.056810 0.321925 0.099 Uiso 1 1 calc R U . . .
C17 C 0.7615(3) 0.29361(18) 0.3995(3) 0.0872(15) Uani 1 1 d . . . . .
H17A H 0.797570 0.302369 0.369321 0.131 Uiso 1 1 calc R U . . .
H17B H 0.773716 0.283353 0.453499 0.131 Uiso 1 1 calc R U . . .
H17C H 0.735221 0.329221 0.399540 0.131 Uiso 1 1 calc R U . . .
C18 C 0.56570(18) 0.1952(2) 0.3111(2) 0.0708(12) Uani 1 1 d . . . . .
H18A H 0.548924 0.159889 0.337536 0.106 Uiso 1 1 calc R U . . .
H18B H 0.554330 0.193876 0.255258 0.106 Uiso 1 1 calc R U . . .
H18C H 0.549671 0.232158 0.334415 0.106 Uiso 1 1 calc R U . . .
C19 C 0.55005(14) 0.01759(17) 0.12580(18) 0.0488(8) Uani 1 1 d . . . . .
H19A H 0.543091 0.053777 0.092661 0.059 Uiso 1 1 calc R U . . .
H19B H 0.510108 0.001104 0.139490 0.059 Uiso 1 1 calc R U . . .
C20 C 0.58398(15) -0.02935(15) 0.07954(17) 0.0454(8) Uani 1 1 d . . . . .
C21 C 0.64552(15) -0.02381(15) 0.06894(18) 0.0480(8) Uani 1 1 d . . . . .
H21A H 0.666732 0.010015 0.090154 0.058 Uiso 1 1 calc R U . . .
C22 C 0.6764(2) -0.06744(18) 0.0275(2) 0.0638(11) Uani 1 1 d . . . . .
H22A H 0.718759 -0.063815 0.020912 0.077 Uiso 1 1 calc R U . . .
C23 C 0.6455(2) -0.11581(19) -0.0040(2) 0.0700(12) Uani 1 1 d . . . . .
H23A H 0.666680 -0.145584 -0.032579 0.084 Uiso 1 1 calc R U . . .
C24 C 0.5843(3) -0.12159(18) 0.0053(2) 0.0749(13) Uani 1 1 d . . . . .
H24A H 0.563416 -0.155238 -0.016891 0.090 Uiso 1 1 calc R U . . .
C25 C 0.5528(2) -0.07833(18) 0.0472(2) 0.0627(11) Uani 1 1 d . . . . .
H25A H 0.510447 -0.082251 0.053626 0.075 Uiso 1 1 calc R U . . .
C26 C 0.59690(15) 0.59395(15) 0.08361(17) 0.0438(8) Uani 1 1 d . . . . .
H26A H 0.606950 0.552980 0.073635 0.053 Uiso 1 1 calc R U . . .
C27 C 0.59956(17) 0.63593(16) 0.0232(2) 0.0546(9) Uani 1 1 d . . . . .
H27A H 0.611656 0.623113 -0.027113 0.066 Uiso 1 1 calc R U . . .
C28 C 0.58496(18) 0.69591(17) 0.0348(2) 0.0602(10) Uani 1 1 d . . . . .
H28A H 0.586992 0.724294 -0.006755 0.072 Uiso 1 1 calc R U . . .
C29 C 0.56738(17) 0.71361(17) 0.1083(2) 0.0575(9) Uani 1 1 d . . . . .
H29A H 0.556932 0.754627 0.117284 0.069 Uiso 1 1 calc R U . . .
C30 C 0.56478(15) 0.67298(14) 0.16835(19) 0.0465(8) Uani 1 1 d . . . . .
H30A H 0.552568 0.686697 0.218232 0.056 Uiso 1 1 calc R U . . .
C31 C 0.57965(13) 0.61090(14) 0.15907(17) 0.0386(7) Uani 1 1 d . . . . .
C32 C 0.57513(13) 0.57174(13) 0.22525(17) 0.0366(7) Uani 1 1 d . . . . .
H32A H 0.558607 0.589231 0.270769 0.044 Uiso 1 1 calc R U . . .
C33 C 0.59175(12) 0.51157(13) 0.23152(16) 0.0340(6) Uani 1 1 d . . . . .
C34 C 0.62144(13) 0.46961(12) 0.18339(17) 0.0349(7) Uani 1 1 d . . . . .
H34A H 0.634160 0.476302 0.131384 0.042 Uiso 1 1 calc R U . . .
C35 C 0.65946(14) 0.36417(13) 0.20124(16) 0.0369(7) Uani 1 1 d . . . . .
C36 C 0.72235(14) 0.36321(13) 0.20835(17) 0.0400(7) Uani 1 1 d . . . . .
C37 C 0.75187(16) 0.31190(15) 0.18219(19) 0.0473(8) Uani 1 1 d . . . . .
H37A H 0.794753 0.310025 0.185722 0.057 Uiso 1 1 calc R U . . .
C38 C 0.71944(19) 0.26308(15) 0.15081(19) 0.0528(9) Uani 1 1 d . . . . .
C39 C 0.65699(19) 0.26611(15) 0.14666(18) 0.0529(9) Uani 1 1 d . . . . .
H39A H 0.634906 0.232334 0.126880 0.064 Uiso 1 1 calc R U . . .
C40 C 0.62551(15) 0.31686(14) 0.17043(17) 0.0430(8) Uani 1 1 d . . . . .
C41 C 0.75761(16) 0.41566(16) 0.2421(2) 0.0535(9) Uani 1 1 d . . . . .
H41A H 0.797782 0.401818 0.259786 0.080 Uiso 1 1 calc R U . . .
H41B H 0.736200 0.432490 0.286614 0.080 Uiso 1 1 calc R U . . .
H41C H 0.761830 0.446845 0.201832 0.080 Uiso 1 1 calc R U . . .
C42 C 0.7528(2) 0.20849(17) 0.1207(2) 0.0783(13) Uani 1 1 d . . . . .
H42A H 0.790122 0.202580 0.151887 0.117 Uiso 1 1 calc R U . . .
H42B H 0.762627 0.214908 0.065665 0.117 Uiso 1 1 calc R U . . .
H42C H 0.727101 0.172602 0.124933 0.117 Uiso 1 1 calc R U . . .
C43 C 0.55746(16) 0.32165(19) 0.1619(2) 0.0642(11) Uani 1 1 d . . . . .
H43A H 0.546732 0.358701 0.133337 0.096 Uiso 1 1 calc R U . . .
H43B H 0.539886 0.322795 0.214002 0.096 Uiso 1 1 calc R U . . .
H43C H 0.541654 0.286566 0.132945 0.096 Uiso 1 1 calc R U . . .
C44 C 0.55576(13) 0.49682(14) 0.37091(16) 0.0377(7) Uani 1 1 d . . . . .
H44A H 0.544961 0.461150 0.402615 0.045 Uiso 1 1 calc R U . . .
H44B H 0.518213 0.519745 0.358905 0.045 Uiso 1 1 calc R U . . .
C45 C 0.59909(14) 0.53630(14) 0.41787(17) 0.0394(7) Uani 1 1 d . . . . .
C46 C 0.58099(18) 0.59396(15) 0.44188(19) 0.0547(9) Uani 1 1 d . . . . .
H46A H 0.541508 0.608303 0.428893 0.066 Uiso 1 1 calc R U . . .
C47 C 0.6209(2) 0.62968(17) 0.4845(2) 0.0669(12) Uani 1 1 d . . . . .
H47A H 0.608501 0.668644 0.500935 0.080 Uiso 1 1 calc R U . . .
C48 C 0.6784(2) 0.61012(18) 0.50361(19) 0.0590(10) Uani 1 1 d . . . . .
H48A H 0.705381 0.635421 0.532811 0.071 Uiso 1 1 calc R U . . .
C49 C 0.69655(17) 0.55362(19) 0.4802(2) 0.0574(9) Uani 1 1 d . . . . .
H49A H 0.736148 0.539732 0.493467 0.069 Uiso 1 1 calc R U . . .
C50 C 0.65723(15) 0.51703(16) 0.43732(19) 0.0479(8) Uani 1 1 d . . . . .
H50A H 0.670212 0.478215 0.420997 0.057 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 N2 1.364(4) . ?
N1 C8 1.396(4) . ?
N1 C19 1.444(4) . ?
C1 C2 1.372(5) . ?
C1 C6 1.410(4) . ?
C1 H1A 0.9500 . ?
N2 N3 1.313(3) . ?
C2 C3 1.386(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(5) . ?
C3 H3A 0.9500 . ?
N3 C9 1.346(4) . ?
N3 C10 1.439(4) . ?
N4 N5 1.357(3) . ?
N4 C33 1.394(4) . ?
N4 C44 1.457(4) . ?
C4 C5 1.366(5) . ?
C4 H4A 0.9500 . ?
N5 N6 1.315(3) . ?
C5 C6 1.420(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.436(4) . ?
N6 C34 1.347(4) . ?
N6 C35 1.448(4) . ?
C7 C8 1.374(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.418(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.385(5) . ?
C10 C15 1.399(4) . ?
C11 C12 1.390(5) . ?
C11 C16 1.508(5) . ?
C12 C13 1.380(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.393(6) . ?
C13 C17 1.510(5) . ?
C14 C15 1.378(5) . ?
C14 H14A 0.9500 . ?
C15 C18 1.495(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.516(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.384(5) . ?
C20 C25 1.391(5) . ?
C21 C22 1.388(5) . ?
C21 H21A 0.9500 . ?
C22 C23 1.371(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.374(6) . ?
C23 H23A 0.9500 . ?
C24 C25 1.394(6) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C27 1.390(4) . ?
C26 C31 1.404(4) . ?
C26 H26A 0.9500 . ?
C27 C28 1.382(5) . ?
C27 H27A 0.9500 . ?
C28 C29 1.380(5) . ?
C28 H28A 0.9500 . ?
C29 C30 1.365(5) . ?
C29 H29A 0.9500 . ?
C30 C31 1.422(4) . ?
C30 H30A 0.9500 . ?
C31 C32 1.429(4) . ?
C32 C33 1.385(4) . ?
C32 H32A 0.9500 . ?
C33 C34 1.414(4) . ?
C34 H34A 0.9500 . ?
C35 C40 1.384(4) . ?
C35 C36 1.394(4) . ?
C36 C37 1.390(4) . ?
C36 C41 1.504(4) . ?
C37 C38 1.396(5) . ?
C37 H37A 0.9500 . ?
C38 C39 1.383(5) . ?
C38 C42 1.513(5) . ?
C39 C40 1.388(5) . ?
C39 H39A 0.9500 . ?
C40 C43 1.512(5) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C45 1.511(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C50 1.387(4) . ?
C45 C46 1.402(4) . ?
C46 C47 1.378(5) . ?
C46 H46A 0.9500 . ?
C47 C48 1.373(6) . ?
C47 H47A 0.9500 . ?
C48 C49 1.376(5) . ?
C48 H48A 0.9500 . ?
C49 C50 1.383(5) . ?
C49 H49A 0.9500 . ?
C50 H50A 0.9500 . ?

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 C8 114.4(2) . . ?
N2 N1 C19 118.6(3) . . ?
C8 N1 C19 126.8(3) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 H1A 119.2 . . ?
C6 C1 H1A 119.2 . . ?
N3 N2 N1 102.3(2) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
N2 N3 C9 114.9(3) . . ?
N2 N3 C10 120.2(3) . . ?
C9 N3 C10 124.9(2) . . ?
N5 N4 C33 114.6(2) . . ?
N5 N4 C44 118.1(2) . . ?
C33 N4 C44 126.9(2) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
N6 N5 N4 102.3(2) . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C1 C6 C5 115.7(3) . . ?
C1 C6 C7 125.7(3) . . ?
C5 C6 C7 118.6(3) . . ?
N5 N6 C34 114.7(2) . . ?
N5 N6 C35 118.7(2) . . ?
C34 N6 C35 126.5(2) . . ?
C8 C7 C6 127.7(3) . . ?
C8 C7 H7A 116.1 . . ?
C6 C7 H7A 116.1 . . ?
C7 C8 N1 123.4(3) . . ?
C7 C8 C9 135.4(3) . . ?
N1 C8 C9 101.2(3) . . ?
N3 C9 C8 107.1(2) . . ?
N3 C9 H9A 126.5 . . ?
C8 C9 H9A 126.5 . . ?
C11 C10 C15 122.8(3) . . ?
C11 C10 N3 118.5(3) . . ?
C15 C10 N3 118.7(3) . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 C16 122.2(3) . . ?
C12 C11 C16 120.2(3) . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 118.6(3) . . ?
C12 C13 C17 120.5(4) . . ?
C14 C13 C17 120.9(4) . . ?
C15 C14 C13 122.2(3) . . ?
C15 C14 H14A 118.9 . . ?
C13 C14 H14A 118.9 . . ?
C14 C15 C10 117.1(3) . . ?
C14 C15 C18 122.6(3) . . ?
C10 C15 C18 120.3(3) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 112.2(3) . . ?
N1 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N1 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C25 119.8(3) . . ?
C21 C20 C19 120.7(3) . . ?
C25 C20 C19 119.5(3) . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22A 120.1 . . ?
C21 C22 H22A 120.1 . . ?
C22 C23 C24 120.6(4) . . ?
C22 C23 H23A 119.7 . . ?
C24 C23 H23A 119.7 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C20 C25 C24 119.3(4) . . ?
C20 C25 H25A 120.4 . . ?
C24 C25 H25A 120.4 . . ?
C27 C26 C31 121.3(3) . . ?
C27 C26 H26A 119.4 . . ?
C31 C26 H26A 119.4 . . ?
C28 C27 C26 121.4(3) . . ?
C28 C27 H27A 119.3 . . ?
C26 C27 H27A 119.3 . . ?
C29 C28 C27 118.4(3) . . ?
C29 C28 H28A 120.8 . . ?
C27 C28 H28A 120.8 . . ?
C30 C29 C28 120.9(3) . . ?
C30 C29 H29A 119.6 . . ?
C28 C29 H29A 119.6 . . ?
C29 C30 C31 122.5(3) . . ?
C29 C30 H30A 118.7 . . ?
C31 C30 H30A 118.7 . . ?
C26 C31 C30 115.4(3) . . ?
C26 C31 C32 126.1(3) . . ?
C30 C31 C32 118.4(3) . . ?
C33 C32 C31 128.3(3) . . ?
C33 C32 H32A 115.8 . . ?
C31 C32 H32A 115.8 . . ?
C32 C33 N4 123.2(3) . . ?
C32 C33 C34 135.5(3) . . ?
N4 C33 C34 101.2(2) . . ?
N6 C34 C33 107.0(2) . . ?
N6 C34 H34A 126.5 . . ?
C33 C34 H34A 126.5 . . ?
C40 C35 C36 123.5(3) . . ?
C40 C35 N6 118.4(3) . . ?
C36 C35 N6 118.1(3) . . ?
C37 C36 C35 117.5(3) . . ?
C37 C36 C41 120.7(3) . . ?
C35 C36 C41 121.9(3) . . ?
C36 C37 C38 121.0(3) . . ?
C36 C37 H37A 119.5 . . ?
C38 C37 H37A 119.5 . . ?
C39 C38 C37 119.0(3) . . ?
C39 C38 C42 121.1(4) . . ?
C37 C38 C42 119.9(4) . . ?
C38 C39 C40 122.2(3) . . ?
C38 C39 H39A 118.9 . . ?
C40 C39 H39A 118.9 . . ?
C35 C40 C39 116.8(3) . . ?
C35 C40 C43 120.8(3) . . ?
C39 C40 C43 122.3(3) . . ?
C36 C41 H41A 109.5 . . ?
C36 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C36 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N4 C44 C45 111.7(2) . . ?
N4 C44 H44A 109.3 . . ?
C45 C44 H44A 109.3 . . ?
N4 C44 H44B 109.3 . . ?
C45 C44 H44B 109.3 . . ?
H44A C44 H44B 107.9 . . ?
C50 C45 C46 118.7(3) . . ?
C50 C45 C44 121.3(3) . . ?
C46 C45 C44 119.9(3) . . ?
C47 C46 C45 119.5(4) . . ?
C47 C46 H46A 120.3 . . ?
C45 C46 H46A 120.3 . . ?
C48 C47 C46 121.4(4) . . ?
C48 C47 H47A 119.3 . . ?
C46 C47 H47A 119.3 . . ?
C47 C48 C49 119.5(3) . . ?
C47 C48 H48A 120.2 . . ?
C49 C48 H48A 120.2 . . ?
C48 C49 C50 120.1(4) . . ?
C48 C49 H49A 120.0 . . ?
C50 C49 H49A 120.0 . . ?
C49 C50 C45 120.8(3) . . ?
C49 C50 H50A 119.6 . . ?
C45 C50 H50A 119.6 . . ?

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
C8 N1 N2 N3 -3.1(3) . . . . ?
C19 N1 N2 N3 -178.9(3) . . . . ?
C6 C1 C2 C3 1.0(6) . . . . ?
C1 C2 C3 C4 -1.6(7) . . . . ?
N1 N2 N3 C9 1.1(3) . . . . ?
N1 N2 N3 C10 -179.8(2) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C33 N4 N5 N6 -2.8(3) . . . . ?
C44 N4 N5 N6 -175.9(2) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C1 C6 C7 179.7(4) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
N4 N5 N6 C34 0.8(3) . . . . ?
N4 N5 N6 C35 178.6(2) . . . . ?
C1 C6 C7 C8 8.0(6) . . . . ?
C5 C6 C7 C8 -172.3(3) . . . . ?
C6 C7 C8 N1 179.7(3) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
N2 N1 C8 C7 -175.5(3) . . . . ?
C19 N1 C8 C7 -0.2(5) . . . . ?
N2 N1 C8 C9 3.8(3) . . . . ?
C19 N1 C8 C9 179.1(3) . . . . ?
N2 N3 C9 C8 1.2(3) . . . . ?
C10 N3 C9 C8 -177.8(3) . . . . ?
C7 C8 C9 N3 176.4(3) . . . . ?
N1 C8 C9 N3 -2.8(3) . . . . ?
N2 N3 C10 C11 -109.9(3) . . . . ?
C9 N3 C10 C11 69.1(4) . . . . ?
N2 N3 C10 C15 73.2(4) . . . . ?
C9 N3 C10 C15 -107.8(3) . . . . ?
C15 C10 C11 C12 2.1(5) . . . . ?
N3 C10 C11 C12 -174.7(3) . . . . ?
C15 C10 C11 C16 -177.6(3) . . . . ?
N3 C10 C11 C16 5.7(5) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C16 C11 C12 C13 178.2(3) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C11 C12 C13 C17 179.2(3) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C17 C13 C14 C15 -178.2(3) . . . . ?
C13 C14 C15 C10 -0.6(5) . . . . ?
C13 C14 C15 C18 178.2(3) . . . . ?
C11 C10 C15 C14 -1.1(5) . . . . ?
N3 C10 C15 C14 175.7(3) . . . . ?
C11 C10 C15 C18 -179.8(3) . . . . ?
N3 C10 C15 C18 -3.1(5) . . . . ?
N2 N1 C19 C20 108.9(3) . . . . ?
C8 N1 C19 C20 -66.2(4) . . . . ?
N1 C19 C20 C21 -43.6(4) . . . . ?
N1 C19 C20 C25 136.6(3) . . . . ?
C25 C20 C21 C22 -1.2(5) . . . . ?
C19 C20 C21 C22 179.1(3) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C21 C22 C23 C24 -0.2(6) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
C21 C20 C25 C24 0.8(5) . . . . ?
C19 C20 C25 C24 -179.5(3) . . . . ?
C23 C24 C25 C20 -0.1(5) . . . . ?
C31 C26 C27 C28 -0.4(6) . . . . ?
C26 C27 C28 C29 -0.1(6) . . . . ?
C27 C28 C29 C30 0.4(6) . . . . ?
C28 C29 C30 C31 -0.1(6) . . . . ?
C27 C26 C31 C30 0.7(5) . . . . ?
C27 C26 C31 C32 179.8(3) . . . . ?
C29 C30 C31 C26 -0.4(5) . . . . ?
C29 C30 C31 C32 -179.6(3) . . . . ?
C26 C31 C32 C33 6.6(5) . . . . ?
C30 C31 C32 C33 -174.3(3) . . . . ?
C31 C32 C33 N4 -176.1(3) . . . . ?
C31 C32 C33 C34 6.0(6) . . . . ?
N5 N4 C33 C32 -175.0(3) . . . . ?
C44 N4 C33 C32 -2.6(4) . . . . ?
N5 N4 C33 C34 3.6(3) . . . . ?
C44 N4 C33 C34 175.9(2) . . . . ?
N5 N6 C34 C33 1.4(3) . . . . ?
C35 N6 C34 C33 -176.2(3) . . . . ?
C32 C33 C34 N6 175.5(3) . . . . ?
N4 C33 C34 N6 -2.8(3) . . . . ?
N5 N6 C35 C40 84.4(3) . . . . ?
C34 N6 C35 C40 -98.2(3) . . . . ?
N5 N6 C35 C36 -97.5(3) . . . . ?
C34 N6 C35 C36 80.0(4) . . . . ?
C40 C35 C36 C37 0.6(4) . . . . ?
N6 C35 C36 C37 -177.5(3) . . . . ?
C40 C35 C36 C41 179.9(3) . . . . ?
N6 C35 C36 C41 1.8(4) . . . . ?
C35 C36 C37 C38 -0.7(5) . . . . ?
C41 C36 C37 C38 -180.0(3) . . . . ?
C36 C37 C38 C39 -0.6(5) . . . . ?
C36 C37 C38 C42 178.3(3) . . . . ?
C37 C38 C39 C40 2.0(5) . . . . ?
C42 C38 C39 C40 -176.8(3) . . . . ?
C36 C35 C40 C39 0.7(4) . . . . ?
N6 C35 C40 C39 178.8(3) . . . . ?
C36 C35 C40 C43 -178.0(3) . . . . ?
N6 C35 C40 C43 0.1(4) . . . . ?
C38 C39 C40 C35 -2.1(5) . . . . ?
C38 C39 C40 C43 176.6(3) . . . . ?
N5 N4 C44 C45 99.5(3) . . . . ?
C33 N4 C44 C45 -72.6(4) . . . . ?
N4 C44 C45 C50 -53.8(4) . . . . ?
N4 C44 C45 C46 125.5(3) . . . . ?
C50 C45 C46 C47 -0.5(5) . . . . ?
C44 C45 C46 C47 -179.8(3) . . . . ?
C45 C46 C47 C48 0.4(6) . . . . ?
C46 C47 C48 C49 -0.3(6) . . . . ?
C47 C48 C49 C50 0.3(5) . . . . ?
C48 C49 C50 C45 -0.5(5) . . . . ?
C46 C45 C50 C49 0.6(5) . . . . ?
C44 C45 C50 C49 179.8(3) . . . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.114



####################################################################### 
# 
# 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_wl475
_database_code_depnum_ccdc_archive 'CCDC 2076295'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 Cl2 N5'
_chemical_formula_weight         360.24

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'
Cl Cl 0.1484 0.1585 '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                   6.907(3)
_cell_length_b                   10.401(4)
_cell_length_c                   12.709(4)
_cell_angle_alpha                102.837(12)
_cell_angle_beta                 102.334(13)
_cell_angle_gamma                99.423(14)
_cell_volume                     848.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    26608
_cell_measurement_theta_min      3.122
_cell_measurement_theta_max      27.437

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.391
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6908
_exptl_absorpt_correction_T_max  0.7382
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26608
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.122
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3838
_reflns_number_gt                2807
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0298P)²+0.2421P] 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         3838
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
Cl1 Cl 0.57164(12) 1.13981(6) 0.77553(5) 0.0597(2) Uani 1 1 d . . . . .
N1 N 0.2908(2) 0.41310(14) 0.60730(12) 0.0245(3) Uani 1 1 d . . . . .
Cl2 Cl 0.87358(9) 1.03755(6) 0.67010(5) 0.0531(2) Uani 1 1 d . . . . .
N2 N 0.3876(2) 0.46479(15) 0.71435(12) 0.0269(3) Uani 1 1 d . . . . .
N3 N 0.4553(2) 0.59749(14) 0.72798(12) 0.0242(3) Uani 1 1 d . . . . .
N4 N 0.3137(2) 0.68280(15) 0.47428(12) 0.0288(4) Uani 1 1 d . . . . .
N5 N 0.4175(2) 0.73679(15) 0.58590(12) 0.0279(3) Uani 1 1 d . . . . .
C8 C 0.0865(3) 0.5390(2) 0.25072(16) 0.0357(5) Uani 1 1 d . . . . .
H8 H 0.137693 0.633796 0.268090 0.043 Uiso 1 1 calc R U . . .
C9 C -0.0220(3) 0.4682(2) 0.14229(17) 0.0426(5) Uani 1 1 d . . . . .
H9 H -0.044683 0.515286 0.086353 0.051 Uiso 1 1 calc R U . . .
C10 C -0.0973(3) 0.3299(2) 0.11472(17) 0.0419(5) Uani 1 1 d . . . . .
H10 H -0.170813 0.281791 0.040384 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0639(3) 0.2634(2) 0.19696(18) 0.0429(5) Uani 1 1 d . . . . .
H11 H -0.115353 0.168513 0.179239 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0438(3) 0.3332(2) 0.30514(17) 0.0359(5) Uani 1 1 d . . . . .
H12 H 0.065514 0.285315 0.360576 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1208(3) 0.47192(18) 0.33436(14) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.2364(3) 0.54836(18) 0.44876(14) 0.0244(4) Uani 1 1 d . . . . .
C15 C 0.2923(2) 0.50962(17) 0.54971(14) 0.0228(4) Uani 1 1 d . . . . .
C16 C 0.3997(3) 0.62925(17) 0.62759(14) 0.0239(4) Uani 1 1 d . . . . .
C17 C 0.5600(3) 0.68365(18) 0.83625(14) 0.0269(4) Uani 1 1 d . . . . .
C18 C 0.6013(3) 0.6300(2) 0.92714(16) 0.0332(4) Uani 1 1 d . . . . .
H18 H 0.563757 0.535440 0.918149 0.040 Uiso 1 1 calc R U . . .
C19 C 0.6985(3) 0.7178(2) 1.03142(17) 0.0403(5) Uani 1 1 d . . . . .
H19 H 0.726585 0.683198 1.094873 0.048 Uiso 1 1 calc R U . . .
C20 C 0.7549(3) 0.8551(2) 1.04382(18) 0.0442(5) Uani 1 1 d . . . . .
H20 H 0.823287 0.914323 1.115435 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7122(4) 0.9065(2) 0.95233(18) 0.0456(5) Uani 1 1 d . . . . .
H21 H 0.749850 1.001110 0.961332 0.055 Uiso 1 1 calc R U . . .
C22 C 0.6144(3) 0.82053(19) 0.84730(16) 0.0353(5) Uani 1 1 d . . . . .
H22 H 0.585335 0.855370 0.784033 0.042 Uiso 1 1 calc R U . . .
C23 C 0.2002(3) 0.26804(18) 0.57034(17) 0.0322(4) Uani 1 1 d . . . . .
H23A H 0.052189 0.253781 0.544558 0.048 Uiso 1 1 calc R U . . .
H23B H 0.234732 0.227815 0.632747 0.048 Uiso 1 1 calc R U . . .
H23C H 0.253076 0.225332 0.508930 0.048 Uiso 1 1 calc R U . . .
C24 C 0.6244(3) 1.0657(2) 0.64816(17) 0.0406(5) Uani 1 1 d . . . . .
H24A H 0.525595 0.978630 0.610807 0.049 Uiso 1 1 calc R U . . .
H24B H 0.608008 1.126064 0.598149 0.049 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
Cl1 C24 1.771(2) . ?
N1 N2 1.325(2) . ?
N1 C15 1.368(2) . ?
N1 C23 1.462(2) . ?
Cl2 C24 1.767(2) . ?
N2 N3 1.342(2) . ?
N3 C16 1.380(2) . ?
N3 C17 1.426(2) . ?
N4 C14 1.351(2) . ?
N4 N5 1.386(2) . ?
N5 C16 1.339(2) . ?
C8 C9 1.389(3) . ?
C8 C13 1.396(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.472(2) . ?
C14 C15 1.423(2) . ?
C15 C16 1.384(2) . ?
C17 C22 1.379(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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 C15 111.85(14) . . ?
N2 N1 C23 117.26(14) . . ?
C15 N1 C23 130.89(15) . . ?
N1 N2 N3 106.32(13) . . ?
N2 N3 C16 110.12(14) . . ?
N2 N3 C17 120.12(14) . . ?
C16 N3 C17 129.69(15) . . ?
C14 N4 N5 112.68(14) . . ?
C16 N5 N4 103.09(14) . . ?
C9 C8 C13 120.55(19) . . ?
C9 C8 H8 119.7 . . ?
C13 C8 H8 119.7 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 118.81(19) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 117.77(17) . . ?
C12 C13 C14 122.35(17) . . ?
C8 C13 C14 119.88(17) . . ?
N4 C14 C15 106.22(15) . . ?
N4 C14 C13 121.10(15) . . ?
C15 C14 C13 132.69(17) . . ?
N1 C15 C16 105.43(15) . . ?
N1 C15 C14 150.64(17) . . ?
C16 C15 C14 103.93(15) . . ?
N5 C16 N3 139.65(17) . . ?
N5 C16 C15 114.08(16) . . ?
N3 C16 C15 106.27(15) . . ?
C22 C17 C18 121.73(17) . . ?
C22 C17 N3 117.95(16) . . ?
C18 C17 N3 120.31(17) . . ?
C19 C18 C17 118.43(19) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C20 C19 C18 120.55(19) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.11(19) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 118.90(19) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Cl2 C24 Cl1 111.60(11) . . ?
Cl2 C24 H24A 109.3 . . ?
Cl1 C24 H24A 109.3 . . ?
Cl2 C24 H24B 109.3 . . ?
Cl1 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?

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
C15 N1 N2 N3 -0.28(18) . . . . ?
C23 N1 N2 N3 -179.62(14) . . . . ?
N1 N2 N3 C16 -0.03(18) . . . . ?
N1 N2 N3 C17 177.47(14) . . . . ?
C14 N4 N5 C16 -0.15(19) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C11 C12 C13 C14 -179.78(18) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C9 C8 C13 C14 179.85(17) . . . . ?
N5 N4 C14 C15 -0.11(19) . . . . ?
N5 N4 C14 C13 179.99(15) . . . . ?
C12 C13 C14 N4 178.43(17) . . . . ?
C8 C13 C14 N4 -1.2(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C8 C13 C14 C15 178.97(18) . . . . ?
N2 N1 C15 C16 0.47(19) . . . . ?
C23 N1 C15 C16 179.68(17) . . . . ?
N2 N1 C15 C14 -178.8(3) . . . . ?
C23 N1 C15 C14 0.4(4) . . . . ?
N4 C14 C15 N1 179.6(3) . . . . ?
C13 C14 C15 N1 -0.6(4) . . . . ?
N4 C14 C15 C16 0.31(18) . . . . ?
C13 C14 C15 C16 -179.81(18) . . . . ?
N4 N5 C16 N3 -179.0(2) . . . . ?
N4 N5 C16 C15 0.4(2) . . . . ?
N2 N3 C16 N5 179.8(2) . . . . ?
C17 N3 C16 N5 2.6(4) . . . . ?
N2 N3 C16 C15 0.31(19) . . . . ?
C17 N3 C16 C15 -176.88(16) . . . . ?
N1 C15 C16 N5 179.94(14) . . . . ?
C14 C15 C16 N5 -0.4(2) . . . . ?
N1 C15 C16 N3 -0.45(18) . . . . ?
C14 C15 C16 N3 179.17(13) . . . . ?
N2 N3 C17 C22 -175.68(16) . . . . ?
C16 N3 C17 C22 1.3(3) . . . . ?
N2 N3 C17 C18 3.1(2) . . . . ?
C16 N3 C17 C18 -179.94(17) . . . . ?
C22 C17 C18 C19 0.5(3) . . . . ?
N3 C17 C18 C19 -178.29(17) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C18 C17 C22 C21 -0.2(3) . . . . ?
N3 C17 C22 C21 178.53(18) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_wl451
_database_code_depnum_ccdc_archive 'CCDC 2076294'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.48

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                   7.9028(7)
_cell_length_b                   12.5696(8)
_cell_length_c                   20.7598(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.571(3)
_cell_angle_gamma                90
_cell_volume                     2052.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    51730
_cell_measurement_theta_min      1.971
_cell_measurement_theta_max      28.159

_exptl_crystal_description       'dark green'
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   0.7019
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6116
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51730
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.971
_diffrn_reflns_theta_max         28.159
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4987
_reflns_number_gt                3740
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0698P)²+0.3432P] 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         4987
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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 0.03986(13) 0.37621(8) 0.41697(5) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.43703(17) 0.34685(10) 0.28757(6) 0.0269(3) Uani 1 1 d . . . . .
H1A H 0.373179 0.285078 0.295692 0.032 Uiso 1 1 calc R U . . .
N2 N 0.04590(14) 0.29459(9) 0.46057(5) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.58641(17) 0.33593(10) 0.25827(6) 0.0297(3) Uani 1 1 d . . . . .
H2A H 0.624443 0.266956 0.247747 0.036 Uiso 1 1 calc R U . . .
C3 C 0.68083(17) 0.42408(11) 0.24415(7) 0.0318(3) Uani 1 1 d . . . . .
H3A H 0.783390 0.416249 0.224243 0.038 Uiso 1 1 calc R U . . .
N3 N 0.19864(13) 0.25398(8) 0.45634(5) 0.0262(2) Uani 1 1 d . . . . .
C4 C 0.62278(16) 0.52419(11) 0.25964(7) 0.0303(3) Uani 1 1 d . . . . .
H4A H 0.684956 0.585627 0.249470 0.036 Uiso 1 1 calc R U . . .
C5 C 0.47548(16) 0.53522(10) 0.28969(6) 0.0265(3) Uani 1 1 d . . . . .
H5A H 0.438916 0.604628 0.300010 0.032 Uiso 1 1 calc R U . . .
C6 C 0.37738(16) 0.44709(9) 0.30562(6) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.22539(16) 0.46265(10) 0.33975(6) 0.0254(3) Uani 1 1 d . . . . .
C8 C 0.13557(15) 0.56577(9) 0.33115(6) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.08343(16) 0.60447(10) 0.26897(6) 0.0267(3) Uani 1 1 d . . . . .
H9A H 0.102588 0.562466 0.232330 0.032 Uiso 1 1 calc R U . . .
C10 C 0.00477(16) 0.70237(10) 0.25978(7) 0.0305(3) Uani 1 1 d . . . . .
H10A H -0.028075 0.726938 0.217120 0.037 Uiso 1 1 calc R U . . .
C11 C -0.02648(17) 0.76489(10) 0.31235(7) 0.0337(3) Uani 1 1 d . . . . .
H11A H -0.082835 0.831367 0.306033 0.040 Uiso 1 1 calc R U . . .
C12 C 0.02545(18) 0.72919(11) 0.37405(7) 0.0339(3) Uani 1 1 d . . . . .
H12A H 0.005845 0.771803 0.410386 0.041 Uiso 1 1 calc R U . . .
C13 C 0.10617(17) 0.63140(10) 0.38336(7) 0.0302(3) Uani 1 1 d . . . . .
H13A H 0.142204 0.608600 0.426127 0.036 Uiso 1 1 calc R U . . .
C14 C 0.18855(16) 0.38825(10) 0.38639(6) 0.0253(3) Uani 1 1 d . . . . .
C15 C 0.28922(16) 0.30415(10) 0.41460(6) 0.0276(3) Uani 1 1 d . . . . .
H15A H 0.401316 0.286541 0.405449 0.033 Uiso 1 1 calc R U . . .
C16 C 0.24758(16) 0.16038(10) 0.49418(6) 0.0252(3) Uani 1 1 d . . . . .
C17 C 0.20216(17) 0.06142(10) 0.46764(6) 0.0273(3) Uani 1 1 d . . . . .
C18 C 0.24368(17) -0.02757(10) 0.50558(6) 0.0297(3) Uani 1 1 d . . . . .
H18A H 0.214610 -0.096146 0.488730 0.036 Uiso 1 1 calc R U . . .
C19 C 0.32656(17) -0.01898(11) 0.56747(7) 0.0302(3) Uani 1 1 d . . . . .
C20 C 0.37314(17) 0.08094(11) 0.59107(7) 0.0326(3) Uani 1 1 d . . . . .
H20A H 0.431972 0.086950 0.633042 0.039 Uiso 1 1 calc R U . . .
C21 C 0.33614(17) 0.17286(11) 0.55498(7) 0.0301(3) Uani 1 1 d . . . . .
C22 C 0.1133(2) 0.05038(12) 0.40039(7) 0.0374(3) Uani 1 1 d . . . . .
H22A H 0.021369 0.102816 0.394145 0.056 Uiso 1 1 calc R U . . .
H22B H 0.065777 -0.021421 0.394792 0.056 Uiso 1 1 calc R U . . .
H22C H 0.194861 0.062561 0.368498 0.056 Uiso 1 1 calc R U . . .
C23 C 0.3642(2) -0.11642(12) 0.60874(8) 0.0420(4) Uani 1 1 d . . . . .
H23A H 0.329212 -0.180180 0.583737 0.063 Uiso 1 1 calc R U . . .
H23B H 0.301440 -0.112456 0.647135 0.063 Uiso 1 1 calc R U . . .
H23C H 0.486418 -0.119959 0.622188 0.063 Uiso 1 1 calc R U . . .
C24 C 0.3906(2) 0.28019(12) 0.58177(8) 0.0434(4) Uani 1 1 d . . . . .
H24A H 0.328886 0.336064 0.556311 0.065 Uiso 1 1 calc R U . . .
H24B H 0.513053 0.289169 0.579473 0.065 Uiso 1 1 calc R U . . .
H24C H 0.365310 0.285178 0.626960 0.065 Uiso 1 1 calc R U . . .
C25 C -0.12029(17) 0.43278(12) 0.40625(7) 0.0361(3) Uani 1 1 d . . . . .
H25A H -0.144162 0.448811 0.360061 0.054 Uiso 1 1 calc R U . . .
H25B H -0.113222 0.499281 0.431000 0.054 Uiso 1 1 calc R U . . .
H25C H -0.211731 0.388469 0.420432 0.054 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 N2 1.3658(14) . ?
N1 C14 1.3969(16) . ?
N1 C25 1.4499(17) . ?
C1 C2 1.3863(19) . ?
C1 C6 1.4087(16) . ?
C1 H1A 0.9500 . ?
N2 N3 1.3213(15) . ?
C2 C3 1.3830(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3877(19) . ?
C3 H3A 0.9500 . ?
N3 C15 1.3347(16) . ?
N3 C16 1.4463(15) . ?
C4 C5 1.3801(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4096(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4658(18) . ?
C7 C14 1.3970(18) . ?
C7 C8 1.4802(17) . ?
C8 C13 1.3993(18) . ?
C8 C9 1.4035(18) . ?
C9 C10 1.3834(18) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3896(19) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.4152(17) . ?
C15 H15A 0.9500 . ?
C16 C21 1.3914(18) . ?
C16 C17 1.3932(18) . ?
C17 C18 1.3889(18) . ?
C17 C22 1.5072(19) . ?
C18 C19 1.389(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3849(19) . ?
C19 C23 1.5077(18) . ?
C20 C21 1.3926(19) . ?
C20 H20A 0.9500 . ?
C21 C24 1.5060(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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 C14 113.93(10) . . ?
N2 N1 C25 116.35(10) . . ?
C14 N1 C25 129.59(11) . . ?
C2 C1 C6 121.77(11) . . ?
C2 C1 H1A 119.1 . . ?
C6 C1 H1A 119.1 . . ?
N3 N2 N1 102.68(9) . . ?
C3 C2 C1 120.90(12) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 C4 118.69(12) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
N2 N3 C15 114.31(10) . . ?
N2 N3 C16 118.43(10) . . ?
C15 N3 C16 127.23(11) . . ?
C5 C4 C3 120.54(12) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 122.29(12) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C1 C6 C5 115.76(11) . . ?
C1 C6 C7 123.99(11) . . ?
C5 C6 C7 120.24(11) . . ?
C14 C7 C6 118.78(11) . . ?
C14 C7 C8 122.68(11) . . ?
C6 C7 C8 117.67(10) . . ?
C13 C8 C9 116.87(11) . . ?
C13 C8 C7 122.45(12) . . ?
C9 C8 C7 120.60(11) . . ?
C10 C9 C8 121.53(12) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 120.51(12) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C12 C11 C10 119.09(12) . . ?
C12 C11 H11A 120.5 . . ?
C10 C11 H11A 120.5 . . ?
C11 C12 C13 120.48(13) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C8 121.49(13) . . ?
C12 C13 H13A 119.3 . . ?
C8 C13 H13A 119.3 . . ?
N1 C14 C7 128.95(11) . . ?
N1 C14 C15 101.24(10) . . ?
C7 C14 C15 129.80(12) . . ?
N3 C15 C14 107.83(11) . . ?
N3 C15 H15A 126.1 . . ?
C14 C15 H15A 126.1 . . ?
C21 C16 C17 123.16(11) . . ?
C21 C16 N3 119.04(11) . . ?
C17 C16 N3 117.80(11) . . ?
C18 C17 C16 117.21(12) . . ?
C18 C17 C22 120.95(12) . . ?
C16 C17 C22 121.84(12) . . ?
C19 C18 C17 121.76(12) . . ?
C19 C18 H18A 119.1 . . ?
C17 C18 H18A 119.1 . . ?
C20 C19 C18 118.89(12) . . ?
C20 C19 C23 120.31(13) . . ?
C18 C19 C23 120.80(13) . . ?
C19 C20 C21 121.83(12) . . ?
C19 C20 H20A 119.1 . . ?
C21 C20 H20A 119.1 . . ?
C16 C21 C20 117.09(12) . . ?
C16 C21 C24 122.45(12) . . ?
C20 C21 C24 120.46(12) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C14 N1 N2 N3 -1.12(14) . . . . ?
C25 N1 N2 N3 175.28(11) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
N1 N2 N3 C15 0.93(14) . . . . ?
N1 N2 N3 C16 -176.87(10) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C2 C1 C6 C5 2.39(18) . . . . ?
C2 C1 C6 C7 -176.63(12) . . . . ?
C4 C5 C6 C1 -1.41(18) . . . . ?
C4 C5 C6 C7 177.66(12) . . . . ?
C1 C6 C7 C14 36.27(18) . . . . ?
C5 C6 C7 C14 -142.72(12) . . . . ?
C1 C6 C7 C8 -154.08(12) . . . . ?
C5 C6 C7 C8 26.94(17) . . . . ?
C14 C7 C8 C13 46.01(18) . . . . ?
C6 C7 C8 C13 -123.22(13) . . . . ?
C14 C7 C8 C9 -137.29(13) . . . . ?
C6 C7 C8 C9 53.48(16) . . . . ?
C13 C8 C9 C10 -0.77(18) . . . . ?
C7 C8 C9 C10 -177.65(12) . . . . ?
C8 C9 C10 C11 -0.69(19) . . . . ?
C9 C10 C11 C12 1.45(19) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C8 -0.8(2) . . . . ?
C9 C8 C13 C12 1.49(19) . . . . ?
C7 C8 C13 C12 178.31(12) . . . . ?
N2 N1 C14 C7 179.95(12) . . . . ?
C25 N1 C14 C7 4.1(2) . . . . ?
N2 N1 C14 C15 0.87(14) . . . . ?
C25 N1 C14 C15 -174.93(13) . . . . ?
C6 C7 C14 N1 -168.31(12) . . . . ?
C8 C7 C14 N1 22.6(2) . . . . ?
C6 C7 C14 C15 10.5(2) . . . . ?
C8 C7 C14 C15 -158.60(13) . . . . ?
N2 N3 C15 C14 -0.43(15) . . . . ?
C16 N3 C15 C14 177.13(11) . . . . ?
N1 C14 C15 N3 -0.26(13) . . . . ?
C7 C14 C15 N3 -179.33(13) . . . . ?
N2 N3 C16 C21 -93.53(15) . . . . ?
C15 N3 C16 C21 88.99(16) . . . . ?
N2 N3 C16 C17 86.11(15) . . . . ?
C15 N3 C16 C17 -91.37(16) . . . . ?
C21 C16 C17 C18 2.24(19) . . . . ?
N3 C16 C17 C18 -177.38(11) . . . . ?
C21 C16 C17 C22 -177.14(12) . . . . ?
N3 C16 C17 C22 3.23(18) . . . . ?
C16 C17 C18 C19 0.18(19) . . . . ?
C22 C17 C18 C19 179.57(12) . . . . ?
C17 C18 C19 C20 -1.9(2) . . . . ?
C17 C18 C19 C23 177.58(12) . . . . ?
C18 C19 C20 C21 1.3(2) . . . . ?
C23 C19 C20 C21 -178.17(13) . . . . ?
C17 C16 C21 C20 -2.8(2) . . . . ?
N3 C16 C21 C20 176.83(11) . . . . ?
C17 C16 C21 C24 177.39(13) . . . . ?
N3 C16 C21 C24 -3.0(2) . . . . ?
C19 C20 C21 C16 0.9(2) . . . . ?
C19 C20 C21 C24 -179.23(13) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.064



####################################################################### 
# 
# 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_wl477
_database_code_depnum_ccdc_archive 'CCDC 2076298'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H23 N3'
_chemical_formula_weight         257.37

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                   13.300(7)
_cell_length_b                   7.486(4)
_cell_length_c                   14.731(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.762(17)
_cell_angle_gamma                90
_cell_volume                     1463.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36557
_cell_measurement_theta_min      3.054
_cell_measurement_theta_max      27.615

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6371
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36557
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_av_R_equivalents  0.1252
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.054
_diffrn_reflns_theta_max         27.615
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3364
_reflns_number_gt                2039
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0617P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1515
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.35221(10) 0.60560(18) 0.14912(10) 0.0255(4) Uani 1 1 d . . . . .
C1 C 0.36235(14) 0.4182(2) 0.44030(12) 0.0289(4) Uani 1 1 d . . . . .
H1 H 0.427291 0.423683 0.417152 0.035 Uiso 1 1 calc R U . . .
N2 N 0.43567(11) 0.58372(18) 0.10275(10) 0.0266(4) Uani 1 1 d . . . . .
C2 C 0.35274(15) 0.3541(2) 0.52756(13) 0.0336(5) Uani 1 1 d . . . . .
H2 H 0.411083 0.314238 0.562420 0.040 Uiso 1 1 calc R U . . .
N3 N 0.49759(10) 0.49998(18) 0.16164(10) 0.0249(4) Uani 1 1 d . . . . .
C3 C 0.26030(15) 0.3467(2) 0.56506(13) 0.0356(5) Uani 1 1 d . . . . .
H3 H 0.254304 0.300160 0.624446 0.043 Uiso 1 1 calc R U . . .
C4 C 0.17664(15) 0.4091(2) 0.51375(13) 0.0345(5) Uani 1 1 d . . . . .
H4 H 0.112654 0.408332 0.538871 0.041 Uiso 1 1 calc R U . . .
C5 C 0.18502(14) 0.4724(2) 0.42666(13) 0.0303(5) Uani 1 1 d . . . . .
H5 H 0.126344 0.515550 0.393446 0.036 Uiso 1 1 calc R U . . .
C6 C 0.27769(13) 0.4754(2) 0.38506(12) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.27912(13) 0.5340(2) 0.29223(12) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.217408 0.580046 0.265758 0.031 Uiso 1 1 calc R U . . .
C8 C 0.35878(13) 0.5319(2) 0.23659(12) 0.0246(4) Uani 1 1 d . . . . .
C9 C 0.45879(13) 0.4665(2) 0.24200(12) 0.0254(4) Uani 1 1 d . . . . .
H9 H 0.492373 0.409430 0.293002 0.030 Uiso 1 1 calc R U . . .
C10 C 0.59713(12) 0.4514(2) 0.13167(12) 0.0276(4) Uani 1 1 d . . . . .
H10A H 0.603151 0.496666 0.069114 0.033 Uiso 1 1 calc R U . . .
H10B H 0.602654 0.319618 0.129856 0.033 Uiso 1 1 calc R U . . .
C11 C 0.68323(12) 0.5252(2) 0.19283(12) 0.0267(4) Uani 1 1 d . . . . .
H11A H 0.687304 0.460291 0.251517 0.032 Uiso 1 1 calc R U . . .
H11B H 0.671053 0.653007 0.205342 0.032 Uiso 1 1 calc R U . . .
C12 C 0.78209(12) 0.5046(2) 0.14716(12) 0.0270(4) Uani 1 1 d . . . . .
H12A H 0.791177 0.377429 0.131091 0.032 Uiso 1 1 calc R U . . .
H12B H 0.778351 0.574507 0.090000 0.032 Uiso 1 1 calc R U . . .
C13 C 0.87314(13) 0.5663(3) 0.20693(13) 0.0359(5) Uani 1 1 d . . . . .
H13A H 0.882949 0.484236 0.259480 0.043 Uiso 1 1 calc R U . . .
H13B H 0.859276 0.686706 0.230906 0.043 Uiso 1 1 calc R U . . .
C14 C 0.96998(14) 0.5732(3) 0.15746(14) 0.0385(5) Uani 1 1 d . . . . .
H14A H 0.962012 0.663055 0.108222 0.046 Uiso 1 1 calc R U . . .
H14B H 1.025448 0.613645 0.200700 0.046 Uiso 1 1 calc R U . . .
C15 C 0.99960(14) 0.3960(2) 0.11655(15) 0.0446(6) Uani 1 1 d . . . . .
H15A H 0.948693 0.361057 0.068739 0.067 Uiso 1 1 calc R U . . .
H15B H 1.004094 0.304291 0.164101 0.067 Uiso 1 1 calc R U . . .
H15C H 1.065127 0.408468 0.090412 0.067 Uiso 1 1 calc R U . . .
C16 C 0.26343(12) 0.6792(2) 0.10046(12) 0.0311(5) Uani 1 1 d . . . . .
H16A H 0.282902 0.738301 0.044890 0.047 Uiso 1 1 calc R U . . .
H16B H 0.231705 0.766382 0.139177 0.047 Uiso 1 1 calc R U . . .
H16C H 0.215666 0.582864 0.084418 0.047 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 N2 1.351(2) . ?
N1 C8 1.399(2) . ?
N1 C16 1.449(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.412(2) . ?
C1 H1 0.9500 . ?
N2 N3 1.3154(19) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
N3 C9 1.346(2) . ?
N3 C10 1.468(2) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.438(2) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.415(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.514(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.522(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 C8 114.47(14) . . ?
N2 N1 C16 117.76(14) . . ?
C8 N1 C16 127.23(14) . . ?
C2 C1 C6 121.40(18) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
N3 N2 N1 102.94(14) . . ?
C3 C2 C1 121.56(18) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
N2 N3 C9 114.16(15) . . ?
N2 N3 C10 117.22(15) . . ?
C9 N3 C10 128.60(14) . . ?
C2 C3 C4 118.21(18) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 120.84(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.36(18) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C5 115.53(17) . . ?
C1 C6 C7 125.52(16) . . ?
C5 C6 C7 118.95(16) . . ?
C8 C7 C6 128.29(16) . . ?
C8 C7 H7 115.9 . . ?
C6 C7 H7 115.9 . . ?
C7 C8 N1 122.55(15) . . ?
C7 C8 C9 136.49(17) . . ?
N1 C8 C9 100.95(15) . . ?
N3 C9 C8 107.42(15) . . ?
N3 C9 H9 126.3 . . ?
C8 C9 H9 126.3 . . ?
N3 C10 C11 113.11(14) . . ?
N3 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N3 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 109.96(15) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 113.00(15) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 113.55(16) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 114.21(16) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C8 N1 N2 N3 -1.78(17) . . . . ?
C16 N1 N2 N3 -173.96(13) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
N1 N2 N3 C9 0.34(17) . . . . ?
N1 N2 N3 C10 178.81(13) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 3.5(2) . . . . ?
C2 C1 C6 C7 -176.19(16) . . . . ?
C4 C5 C6 C1 -3.2(2) . . . . ?
C4 C5 C6 C7 176.50(16) . . . . ?
C1 C6 C7 C8 6.2(3) . . . . ?
C5 C6 C7 C8 -173.56(16) . . . . ?
C6 C7 C8 N1 -175.09(16) . . . . ?
C6 C7 C8 C9 6.0(3) . . . . ?
N2 N1 C8 C7 -176.87(14) . . . . ?
C16 N1 C8 C7 -5.6(3) . . . . ?
N2 N1 C8 C9 2.38(17) . . . . ?
C16 N1 C8 C9 173.69(15) . . . . ?
N2 N3 C9 C8 1.13(18) . . . . ?
C10 N3 C9 C8 -177.13(15) . . . . ?
C7 C8 C9 N3 177.09(19) . . . . ?
N1 C8 C9 N3 -1.99(17) . . . . ?
N2 N3 C10 C11 123.85(16) . . . . ?
C9 N3 C10 C11 -57.9(2) . . . . ?
N3 C10 C11 C12 -167.81(13) . . . . ?
C10 C11 C12 C13 -176.74(15) . . . . ?
C11 C12 C13 C14 -171.22(15) . . . . ?
C12 C13 C14 C15 -58.1(2) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.077



####################################################################### 
# 
# 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_wl482
_database_code_depnum_ccdc_archive 'CCDC 2076300'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 F3 N5'
_chemical_formula_weight         343.32

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'
F F 0.0171 0.0103 '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                   11.812(6)
_cell_length_b                   11.965(6)
_cell_length_c                   13.312(6)
_cell_angle_alpha                115.153(14)
_cell_angle_beta                 99.218(15)
_cell_angle_gamma                109.557(14)
_cell_volume                     1500.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    32131
_cell_measurement_theta_min      2.107
_cell_measurement_theta_max      27.560

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32131
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.107
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6893
_reflns_number_gt                4525
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0398P)²+1.5345P] 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         6893
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
F1 F -0.02979(15) 0.12755(18) 0.08721(16) 0.0450(5) Uani 1 1 d . . . . .
N1 N 0.32985(19) -0.0123(2) 0.59073(18) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.8039(3) 0.2866(3) 0.7681(2) 0.0342(6) Uani 1 1 d . . . . .
H1 H 0.820479 0.334885 0.726868 0.041 Uiso 1 1 calc R U . . .
F2 F -0.15473(16) -0.08351(17) 0.02469(14) 0.0436(4) Uani 1 1 d . . . . .
N2 N 0.2243(2) -0.0402(2) 0.51277(18) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.9045(3) 0.3105(3) 0.8569(3) 0.0395(7) Uani 1 1 d . . . . .
H2 H 0.989486 0.374738 0.875418 0.047 Uiso 1 1 calc R U . . .
F3 F -0.17278(16) 0.07813(18) 0.16251(15) 0.0428(4) Uani 1 1 d . . . . .
N3 N 0.26412(19) 0.0411(2) 0.46733(18) 0.0238(5) Uani 1 1 d . . . . .
C3 C 0.8830(3) 0.2423(3) 0.9185(3) 0.0374(7) Uani 1 1 d . . . . .
H3 H 0.952326 0.260315 0.979939 0.045 Uiso 1 1 calc R U . . .
F4 F 0.10834(16) 0.58268(17) 0.42730(15) 0.0448(4) Uani 1 1 d . . . . .
N4 N 0.5969(2) 0.2435(2) 0.59144(19) 0.0279(5) Uani 1 1 d . . . . .
C4 C 0.7601(3) 0.1481(3) 0.8901(2) 0.0365(7) Uani 1 1 d . . . . .
H4 H 0.744349 0.100361 0.931928 0.044 Uiso 1 1 calc R U . . .
F5 F 0.12464(19) 0.42415(19) 0.28504(15) 0.0506(5) Uani 1 1 d . . . . .
N5 N 0.48669(19) 0.2128(2) 0.50894(19) 0.0269(5) Uani 1 1 d . . . . .
C5 C 0.6587(3) 0.1221(3) 0.8006(2) 0.0289(6) Uani 1 1 d . . . . .
H5 H 0.574399 0.055459 0.780934 0.035 Uiso 1 1 calc R U . . .
F6 F -0.02168(16) 0.3705(2) 0.35675(17) 0.0552(5) Uani 1 1 d . . . . .
N6 N 0.61939(19) 0.5113(2) 0.85820(18) 0.0260(5) Uani 1 1 d . . . . .
C6 C 0.6787(2) 0.1922(2) 0.7392(2) 0.0245(5) Uani 1 1 d . . . . .
N7 N 0.5711(2) 0.5348(2) 0.77624(19) 0.0270(5) Uani 1 1 d . . . . .
C7 C 0.5726(2) 0.1704(2) 0.6465(2) 0.0238(5) Uani 1 1 d . . . . .
N8 N 0.44485(19) 0.4461(2) 0.72635(19) 0.0254(5) Uani 1 1 d . . . . .
C8 C 0.4383(2) 0.0853(2) 0.5980(2) 0.0230(5) Uani 1 1 d . . . . .
N9 N 0.3640(2) 0.2423(2) 0.85482(19) 0.0278(5) Uani 1 1 d . . . . .
C9 C 0.3946(2) 0.1189(2) 0.5166(2) 0.0232(5) Uani 1 1 d . . . . .
N10 N 0.3123(2) 0.2667(2) 0.76836(19) 0.0270(5) Uani 1 1 d . . . . .
C10 C 0.1736(2) 0.0395(2) 0.3808(2) 0.0239(5) Uani 1 1 d . . . . .
C11 C 0.0428(2) -0.0349(3) 0.3497(2) 0.0295(6) Uani 1 1 d . . . . .
H11 H 0.010914 -0.086623 0.385408 0.035 Uiso 1 1 calc R U . . .
C12 C -0.0405(3) -0.0327(3) 0.2659(2) 0.0308(6) Uani 1 1 d . . . . .
H12 H -0.130673 -0.083391 0.243338 0.037 Uiso 1 1 calc R U . . .
C13 C 0.0074(2) 0.0433(3) 0.2149(2) 0.0253(5) Uani 1 1 d . . . . .
C14 C 0.1380(2) 0.1173(3) 0.2464(2) 0.0280(6) Uani 1 1 d . . . . .
H14 H 0.169705 0.168895 0.210512 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2234(2) 0.1160(3) 0.3311(2) 0.0270(6) Uani 1 1 d . . . . .
H15 H 0.313594 0.166710 0.353930 0.032 Uiso 1 1 calc R U . . .
C16 C -0.0851(2) 0.0425(3) 0.1237(2) 0.0291(6) Uani 1 1 d . . . . .
C17 C 0.3156(3) -0.0888(3) 0.6526(2) 0.0313(6) Uani 1 1 d . . . . .
H17A H 0.225020 -0.154480 0.624306 0.047 Uiso 1 1 calc R U . . .
H17B H 0.344945 -0.023996 0.738155 0.047 Uiso 1 1 calc R U . . .
H17C H 0.367233 -0.139241 0.637046 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4996(3) 0.2090(3) 1.0281(3) 0.0362(7) Uani 1 1 d . . . . .
H18 H 0.410814 0.148148 0.984138 0.043 Uiso 1 1 calc R U . . .
C19 C 0.5646(3) 0.1933(3) 1.1135(3) 0.0435(7) Uani 1 1 d . . . . .
H19 H 0.520085 0.122059 1.127376 0.052 Uiso 1 1 calc R U . . .
C20 C 0.6941(3) 0.2808(3) 1.1789(2) 0.0378(7) Uani 1 1 d . . . . .
H20 H 0.739167 0.270393 1.237558 0.045 Uiso 1 1 calc R U . . .
C21 C 0.7561(3) 0.3836(3) 1.1567(3) 0.0381(7) Uani 1 1 d . . . . .
H21 H 0.845012 0.444034 1.200320 0.046 Uiso 1 1 calc R U . . .
C22 C 0.6911(3) 0.3999(3) 1.0723(2) 0.0340(6) Uani 1 1 d . . . . .
H22 H 0.735540 0.472312 1.059720 0.041 Uiso 1 1 calc R U . . .
C23 C 0.5618(2) 0.3120(3) 1.0055(2) 0.0276(6) Uani 1 1 d . . . . .
C24 C 0.4914(2) 0.3245(2) 0.9133(2) 0.0249(5) Uani 1 1 d . . . . .
C25 C 0.5289(2) 0.4095(2) 0.8639(2) 0.0245(5) Uani 1 1 d . . . . .
C26 C 0.4153(2) 0.3674(2) 0.7786(2) 0.0248(5) Uani 1 1 d . . . . .
C27 C 0.3607(2) 0.4463(2) 0.6373(2) 0.0257(5) Uani 1 1 d . . . . .
C28 C 0.2309(2) 0.3612(3) 0.5989(2) 0.0273(6) Uani 1 1 d . . . . .
H28 H 0.200809 0.301607 0.628437 0.033 Uiso 1 1 calc R U . . .
C29 C 0.1453(2) 0.3638(3) 0.5169(2) 0.0288(6) Uani 1 1 d . . . . .
H29 H 0.055726 0.307058 0.490711 0.035 Uiso 1 1 calc R U . . .
C30 C 0.1905(3) 0.4492(3) 0.4732(2) 0.0290(6) Uani 1 1 d . . . . .
C31 C 0.3217(3) 0.5316(3) 0.5101(2) 0.0313(6) Uani 1 1 d . . . . .
H31 H 0.352262 0.588242 0.478113 0.038 Uiso 1 1 calc R U . . .
C32 C 0.4073(3) 0.5309(3) 0.5934(2) 0.0319(6) Uani 1 1 d . . . . .
H32 H 0.496897 0.587907 0.620017 0.038 Uiso 1 1 calc R U . . .
C33 C 0.1003(3) 0.4562(3) 0.3858(3) 0.0346(6) Uani 1 1 d . . . . .
C34 C 0.7567(2) 0.5964(3) 0.9279(2) 0.0325(6) Uani 1 1 d . . . . .
H34A H 0.798164 0.536340 0.921624 0.049 Uiso 1 1 calc R U . . .
H34B H 0.768730 0.654110 1.011219 0.049 Uiso 1 1 calc R U . . .
H34C H 0.795246 0.655660 0.897520 0.049 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
F1 C16 1.332(3) . ?
N1 N2 1.325(3) . ?
N1 C8 1.370(3) . ?
N1 C17 1.459(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.393(4) . ?
C1 H1 0.9500 . ?
F2 C16 1.349(3) . ?
N2 N3 1.348(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
F3 C16 1.342(3) . ?
N3 C9 1.367(3) . ?
N3 C10 1.429(3) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
F4 C33 1.335(3) . ?
N4 C7 1.351(3) . ?
N4 N5 1.384(3) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
F5 C33 1.338(3) . ?
N5 C9 1.330(3) . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
F6 C33 1.331(3) . ?
N6 N7 1.328(3) . ?
N6 C25 1.365(3) . ?
N6 C34 1.462(3) . ?
C6 C7 1.475(3) . ?
N7 N8 1.347(3) . ?
C7 C8 1.414(3) . ?
N8 C26 1.381(3) . ?
N8 C27 1.421(3) . ?
C8 C9 1.391(3) . ?
N9 C24 1.350(3) . ?
N9 N10 1.401(3) . ?
N10 C26 1.333(3) . ?
C10 C15 1.379(3) . ?
C10 C11 1.383(4) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(4) . ?
C13 C16 1.493(4) . ?
C14 C15 1.396(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.383(4) . ?
C18 C23 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.461(4) . ?
C24 C25 1.423(4) . ?
C25 C26 1.385(4) . ?
C27 C32 1.379(4) . ?
C27 C28 1.383(4) . ?
C28 C29 1.382(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(4) . ?
C30 C33 1.496(4) . ?
C31 C32 1.380(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

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 C8 112.6(2) . . ?
N2 N1 C17 117.4(2) . . ?
C8 N1 C17 130.0(2) . . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
N1 N2 N3 105.40(19) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
N2 N3 C9 110.8(2) . . ?
N2 N3 C10 120.6(2) . . ?
C9 N3 C10 128.6(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C7 N4 N5 112.5(2) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C9 N5 N4 103.1(2) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N7 N6 C25 112.7(2) . . ?
N7 N6 C34 117.0(2) . . ?
C25 N6 C34 130.3(2) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 122.4(2) . . ?
C1 C6 C7 119.6(2) . . ?
N6 N7 N8 105.60(19) . . ?
N4 C7 C8 106.6(2) . . ?
N4 C7 C6 120.0(2) . . ?
C8 C7 C6 133.4(2) . . ?
N7 N8 C26 110.1(2) . . ?
N7 N8 C27 121.2(2) . . ?
C26 N8 C27 128.6(2) . . ?
N1 C8 C9 104.7(2) . . ?
N1 C8 C7 151.9(2) . . ?
C9 C8 C7 103.4(2) . . ?
C24 N9 N10 112.9(2) . . ?
N5 C9 N3 139.2(2) . . ?
N5 C9 C8 114.4(2) . . ?
N3 C9 C8 106.5(2) . . ?
C26 N10 N9 102.1(2) . . ?
C15 C10 C11 122.1(2) . . ?
C15 C10 N3 116.7(2) . . ?
C11 C10 N3 121.1(2) . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 C16 120.4(2) . . ?
C12 C13 C16 118.7(2) . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 118.4(2) . . ?
C10 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F1 C16 F3 106.4(2) . . ?
F1 C16 F2 105.8(2) . . ?
F3 C16 F2 104.7(2) . . ?
F1 C16 C13 113.9(2) . . ?
F3 C16 C13 112.4(2) . . ?
F2 C16 C13 113.0(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C23 C18 H18 119.4 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 118.4(3) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 117.8(3) . . ?
C22 C23 C24 122.1(2) . . ?
C18 C23 C24 120.1(2) . . ?
N9 C24 C25 106.3(2) . . ?
N9 C24 C23 120.4(2) . . ?
C25 C24 C23 133.3(2) . . ?
N6 C25 C26 104.9(2) . . ?
N6 C25 C24 151.6(2) . . ?
C26 C25 C24 103.6(2) . . ?
N10 C26 N8 138.1(2) . . ?
N10 C26 C25 115.2(2) . . ?
N8 C26 C25 106.7(2) . . ?
C32 C27 C28 121.6(3) . . ?
C32 C27 N8 120.9(2) . . ?
C28 C27 N8 117.4(2) . . ?
C29 C28 C27 119.1(2) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.5(3) . . ?
C29 C30 C33 121.2(2) . . ?
C31 C30 C33 118.4(2) . . ?
C32 C31 C30 119.9(2) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C27 C32 C31 119.0(2) . . ?
C27 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
F6 C33 F4 106.9(2) . . ?
F6 C33 F5 107.2(2) . . ?
F4 C33 F5 105.5(2) . . ?
F6 C33 C30 112.0(2) . . ?
F4 C33 C30 112.4(2) . . ?
F5 C33 C30 112.3(2) . . ?
N6 C34 H34A 109.5 . . ?
N6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

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
C8 N1 N2 N3 0.0(3) . . . . ?
C17 N1 N2 N3 -178.7(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
N1 N2 N3 C9 0.4(3) . . . . ?
N1 N2 N3 C10 -178.79(19) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C7 N4 N5 C9 0.3(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 C7 -177.9(2) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C1 C6 C7 178.7(2) . . . . ?
C25 N6 N7 N8 0.2(3) . . . . ?
C34 N6 N7 N8 -179.2(2) . . . . ?
N5 N4 C7 C8 0.2(3) . . . . ?
N5 N4 C7 C6 -178.7(2) . . . . ?
C5 C6 C7 N4 178.5(2) . . . . ?
C1 C6 C7 N4 -1.0(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C1 C6 C7 C8 -179.5(3) . . . . ?
N6 N7 N8 C26 0.1(3) . . . . ?
N6 N7 N8 C27 177.3(2) . . . . ?
N2 N1 C8 C9 -0.4(3) . . . . ?
C17 N1 C8 C9 178.1(2) . . . . ?
N2 N1 C8 C7 179.0(4) . . . . ?
C17 N1 C8 C7 -2.5(6) . . . . ?
N4 C7 C8 N1 180.0(4) . . . . ?
C6 C7 C8 N1 -1.4(7) . . . . ?
N4 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C9 178.0(2) . . . . ?
N4 N5 C9 N3 179.3(3) . . . . ?
N4 N5 C9 C8 -0.7(3) . . . . ?
N2 N3 C9 N5 179.4(3) . . . . ?
C10 N3 C9 N5 -1.5(5) . . . . ?
N2 N3 C9 C8 -0.6(3) . . . . ?
C10 N3 C9 C8 178.5(2) . . . . ?
N1 C8 C9 N5 -179.4(2) . . . . ?
C7 C8 C9 N5 0.9(3) . . . . ?
N1 C8 C9 N3 0.6(2) . . . . ?
C7 C8 C9 N3 -179.14(19) . . . . ?
C24 N9 N10 C26 -0.1(3) . . . . ?
N2 N3 C10 C15 -174.2(2) . . . . ?
C9 N3 C10 C15 6.8(4) . . . . ?
N2 N3 C10 C11 6.1(3) . . . . ?
C9 N3 C10 C11 -172.9(2) . . . . ?
C15 C10 C11 C12 0.2(4) . . . . ?
N3 C10 C11 C12 179.8(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C11 C12 C13 C16 179.4(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C16 C13 C14 C15 -179.4(2) . . . . ?
C11 C10 C15 C14 -0.2(4) . . . . ?
N3 C10 C15 C14 -179.9(2) . . . . ?
C13 C14 C15 C10 0.2(4) . . . . ?
C14 C13 C16 F1 -5.9(3) . . . . ?
C12 C13 C16 F1 174.8(2) . . . . ?
C14 C13 C16 F3 -127.0(3) . . . . ?
C12 C13 C16 F3 53.7(3) . . . . ?
C14 C13 C16 F2 114.8(3) . . . . ?
C12 C13 C16 F2 -64.4(3) . . . . ?
C23 C18 C19 C20 0.1(5) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -1.1(4) . . . . ?
C21 C22 C23 C18 1.2(4) . . . . ?
C21 C22 C23 C24 -178.3(2) . . . . ?
C19 C18 C23 C22 -0.7(4) . . . . ?
C19 C18 C23 C24 178.8(3) . . . . ?
N10 N9 C24 C25 -0.1(3) . . . . ?
N10 N9 C24 C23 -179.1(2) . . . . ?
C22 C23 C24 N9 -176.2(2) . . . . ?
C18 C23 C24 N9 4.3(4) . . . . ?
C22 C23 C24 C25 5.2(4) . . . . ?
C18 C23 C24 C25 -174.3(3) . . . . ?
N7 N6 C25 C26 -0.4(3) . . . . ?
C34 N6 C25 C26 178.9(2) . . . . ?
N7 N6 C25 C24 -179.8(4) . . . . ?
C34 N6 C25 C24 -0.6(6) . . . . ?
N9 C24 C25 N6 179.7(4) . . . . ?
C23 C24 C25 N6 -1.5(7) . . . . ?
N9 C24 C25 C26 0.3(3) . . . . ?
C23 C24 C25 C26 179.1(3) . . . . ?
N9 N10 C26 N8 179.6(3) . . . . ?
N9 N10 C26 C25 0.3(3) . . . . ?
N7 N8 C26 N10 -179.7(3) . . . . ?
C27 N8 C26 N10 3.4(5) . . . . ?
N7 N8 C26 C25 -0.3(3) . . . . ?
C27 N8 C26 C25 -177.2(2) . . . . ?
N6 C25 C26 N10 179.9(2) . . . . ?
C24 C25 C26 N10 -0.4(3) . . . . ?
N6 C25 C26 N8 0.4(3) . . . . ?
C24 C25 C26 N8 -179.9(2) . . . . ?
N7 N8 C27 C32 4.4(3) . . . . ?
C26 N8 C27 C32 -178.9(2) . . . . ?
N7 N8 C27 C28 -174.0(2) . . . . ?
C26 N8 C27 C28 2.6(4) . . . . ?
C32 C27 C28 C29 -1.8(4) . . . . ?
N8 C27 C28 C29 176.6(2) . . . . ?
C27 C28 C29 C30 1.1(4) . . . . ?
C28 C29 C30 C31 0.7(4) . . . . ?
C28 C29 C30 C33 -179.0(2) . . . . ?
C29 C30 C31 C32 -1.7(4) . . . . ?
C33 C30 C31 C32 178.0(2) . . . . ?
C28 C27 C32 C31 0.8(4) . . . . ?
N8 C27 C32 C31 -177.6(2) . . . . ?
C30 C31 C32 C27 0.9(4) . . . . ?
C29 C30 C33 F6 -1.4(4) . . . . ?
C31 C30 C33 F6 178.9(2) . . . . ?
C29 C30 C33 F4 119.0(3) . . . . ?
C31 C30 C33 F4 -60.7(3) . . . . ?
C29 C30 C33 F5 -122.2(3) . . . . ?
C31 C30 C33 F5 58.1(3) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_wl476
_database_code_depnum_ccdc_archive 'CCDC 2076301'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 F3 N5'
_chemical_formula_weight         329.29

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'
F F 0.0171 0.0103 '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                   7.229(2)
_cell_length_b                   7.692(2)
_cell_length_c                   13.893(4)
_cell_angle_alpha                100.422(10)
_cell_angle_beta                 93.394(11)
_cell_angle_gamma                101.959(11)
_cell_volume                     739.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    25281
_cell_measurement_theta_min      2.997
_cell_measurement_theta_max      27.562

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25281
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3376
_reflns_number_gt                2403
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0659P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.051(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3376
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
F1 F 0.44136(12) 0.68861(13) 0.14645(6) 0.0508(3) Uani 1 1 d . . . . .
N1 N 0.73162(14) 0.25280(12) 0.49866(7) 0.0217(2) Uani 1 1 d . . . . .
C1 C 1.00866(18) 0.79410(18) 0.76258(9) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.996325 0.895684 0.734726 0.039 Uiso 1 1 calc R U . . .
F2 F 0.30995(12) 0.37601(14) 0.01332(5) 0.0549(3) Uani 1 1 d . . . . .
N2 N 0.64516(14) 0.20627(13) 0.40763(7) 0.0241(2) Uani 1 1 d . . . . .
C2 C 1.0887(2) 0.8206(2) 0.85821(10) 0.0407(4) Uani 1 1 d . . . . .
H2 H 1.131436 0.940338 0.895529 0.049 Uiso 1 1 calc R U . . .
N3 N 0.63104(13) 0.36243(13) 0.38060(7) 0.0212(2) Uani 1 1 d . . . . .
F3 F 0.33178(13) 0.05538(12) 0.06174(6) 0.0588(3) Uani 1 1 d . . . . .
C3 C 1.10745(19) 0.6742(2) 0.90030(10) 0.0413(4) Uani 1 1 d . . . . .
H3 H 1.161299 0.693187 0.966426 0.050 Uiso 1 1 calc R U . . .
N4 N 0.83139(14) 0.73775(13) 0.56755(7) 0.0256(2) Uani 1 1 d . . . . .
C4 C 1.04731(19) 0.5010(2) 0.84547(10) 0.0376(3) Uani 1 1 d . . . . .
H4 H 1.060936 0.400092 0.873670 0.045 Uiso 1 1 calc R U . . .
C5 C 0.96660(18) 0.47325(18) 0.74881(9) 0.0304(3) Uani 1 1 d . . . . .
H5 H 0.925611 0.353228 0.711671 0.037 Uiso 1 1 calc R U . . .
N5 N 0.74088(15) 0.68872(13) 0.47260(7) 0.0250(3) Uani 1 1 d . . . . .
C6 C 0.94526(16) 0.61832(16) 0.70608(8) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.85465(16) 0.59314(15) 0.60534(8) 0.0206(3) Uani 1 1 d . . . . .
C12 C 0.45606(19) 0.5299(2) 0.17106(10) 0.0348(3) Uani 1 1 d . . . . .
C11 C 0.53702(17) 0.52868(18) 0.26305(9) 0.0285(3) Uani 1 1 d . . . . .
H11 H 0.584608 0.638198 0.309586 0.034 Uiso 1 1 calc R U . . .
C10 C 0.54672(16) 0.36244(17) 0.28542(8) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.70960(16) 0.50771(15) 0.45485(8) 0.0199(3) Uani 1 1 d . . . . .
C8 C 0.77432(15) 0.43662(14) 0.53183(8) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.38786(19) 0.3721(2) 0.10266(9) 0.0388(4) Uani 1 1 d . . . . .
C15 C 0.47824(18) 0.20016(18) 0.21951(9) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.484947 0.087257 0.236500 0.038 Uiso 1 1 calc R U . . .
C16 C 0.76902(19) 0.10594(16) 0.54533(10) 0.0312(3) Uani 1 1 d . . . . .
H16A H 0.727346 -0.009839 0.498709 0.047 Uiso 1 1 calc R U . . .
H16B H 0.699252 0.102347 0.603573 0.047 Uiso 1 1 calc R U . . .
H16C H 0.905513 0.126934 0.564984 0.047 Uiso 1 1 calc R U . . .
C14 C 0.40014(19) 0.2095(2) 0.12842(9) 0.0387(4) Uani 1 1 d . . . . .


_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
F1 C12 1.3488(16) . ?
N1 N2 1.3297(14) . ?
N1 C8 1.3687(15) . ?
N1 C16 1.4630(15) . ?
C1 C2 1.3797(18) . ?
C1 C6 1.4038(19) . ?
C1 H1 0.9500 . ?
F2 C13 1.3402(15) . ?
N2 N3 1.3430(13) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
N3 C9 1.3732(15) . ?
N3 C10 1.4229(15) . ?
F3 C14 1.3467(16) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
N4 C7 1.3488(14) . ?
N4 N5 1.3878(14) . ?
C4 C5 1.3932(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3862(17) . ?
C5 H5 0.9500 . ?
N5 C9 1.3376(15) . ?
C6 C7 1.4718(16) . ?
C7 C8 1.4230(16) . ?
C12 C11 1.3761(17) . ?
C12 C13 1.378(2) . ?
C11 C10 1.3838(17) . ?
C11 H11 0.9500 . ?
C10 C15 1.3850(18) . ?
C9 C8 1.3856(16) . ?
C13 C14 1.380(2) . ?
C15 C14 1.3750(18) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 C8 112.02(9) . . ?
N2 N1 C16 117.00(9) . . ?
C8 N1 C16 130.97(10) . . ?
C2 C1 C6 120.59(13) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
N1 N2 N3 105.78(9) . . ?
C1 C2 C3 120.60(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
N2 N3 C9 110.63(9) . . ?
N2 N3 C10 120.72(9) . . ?
C9 N3 C10 128.63(10) . . ?
C4 C3 C2 119.47(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C7 N4 N5 112.52(9) . . ?
C3 C4 C5 120.23(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.93(13) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C9 N5 N4 102.93(9) . . ?
C5 C6 C1 118.18(12) . . ?
C5 C6 C7 122.20(11) . . ?
C1 C6 C7 119.60(11) . . ?
N4 C7 C8 106.67(10) . . ?
N4 C7 C6 120.34(10) . . ?
C8 C7 C6 132.98(10) . . ?
F1 C12 C11 119.77(13) . . ?
F1 C12 C13 118.52(12) . . ?
C11 C12 C13 121.71(13) . . ?
C12 C11 C10 117.71(13) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C10 C15 122.68(12) . . ?
C11 C10 N3 117.35(11) . . ?
C15 C10 N3 119.97(11) . . ?
N5 C9 N3 139.20(10) . . ?
N5 C9 C8 114.46(10) . . ?
N3 C9 C8 106.33(10) . . ?
N1 C8 C9 105.23(10) . . ?
N1 C8 C7 151.33(10) . . ?
C9 C8 C7 103.42(10) . . ?
F2 C13 C12 120.87(14) . . ?
F2 C13 C14 120.62(13) . . ?
C12 C13 C14 118.51(12) . . ?
C14 C15 C10 117.13(13) . . ?
C14 C15 H15 121.4 . . ?
C10 C15 H15 121.4 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F3 C14 C15 119.34(14) . . ?
F3 C14 C13 118.39(12) . . ?
C15 C14 C13 122.26(13) . . ?

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
C8 N1 N2 N3 0.04(12) . . . . ?
C16 N1 N2 N3 -178.63(9) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
N1 N2 N3 C9 0.23(12) . . . . ?
N1 N2 N3 C10 179.14(9) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C7 N4 N5 C9 0.29(13) . . . . ?
C4 C5 C6 C1 0.53(18) . . . . ?
C4 C5 C6 C7 -177.87(11) . . . . ?
C2 C1 C6 C5 -0.42(19) . . . . ?
C2 C1 C6 C7 178.02(11) . . . . ?
N5 N4 C7 C8 -0.29(13) . . . . ?
N5 N4 C7 C6 -178.99(10) . . . . ?
C5 C6 C7 N4 177.96(10) . . . . ?
C1 C6 C7 N4 -0.42(17) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C1 C6 C7 C8 -178.72(12) . . . . ?
F1 C12 C11 C10 179.15(10) . . . . ?
C13 C12 C11 C10 -0.51(19) . . . . ?
C12 C11 C10 C15 -0.21(18) . . . . ?
C12 C11 C10 N3 179.86(10) . . . . ?
N2 N3 C10 C11 179.90(9) . . . . ?
C9 N3 C10 C11 -1.41(17) . . . . ?
N2 N3 C10 C15 -0.04(17) . . . . ?
C9 N3 C10 C15 178.66(11) . . . . ?
N4 N5 C9 N3 -179.51(14) . . . . ?
N4 N5 C9 C8 -0.18(13) . . . . ?
N2 N3 C9 N5 178.97(13) . . . . ?
C10 N3 C9 N5 0.2(2) . . . . ?
N2 N3 C9 C8 -0.40(13) . . . . ?
C10 N3 C9 C8 -179.20(10) . . . . ?
N2 N1 C8 C9 -0.28(12) . . . . ?
C16 N1 C8 C9 178.15(11) . . . . ?
N2 N1 C8 C7 -178.58(19) . . . . ?
C16 N1 C8 C7 -0.1(3) . . . . ?
N5 C9 C8 N1 -179.15(9) . . . . ?
N3 C9 C8 N1 0.40(12) . . . . ?
N5 C9 C8 C7 0.01(13) . . . . ?
N3 C9 C8 C7 179.56(9) . . . . ?
N4 C7 C8 N1 178.48(19) . . . . ?
C6 C7 C8 N1 -3.1(3) . . . . ?
N4 C7 C8 C9 0.16(12) . . . . ?
C6 C7 C8 C9 178.63(12) . . . . ?
F1 C12 C13 F2 0.53(19) . . . . ?
C11 C12 C13 F2 -179.81(11) . . . . ?
F1 C12 C13 C14 -178.97(11) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C10 C15 C14 0.70(19) . . . . ?
N3 C10 C15 C14 -179.37(10) . . . . ?
C10 C15 C14 F3 179.93(11) . . . . ?
C10 C15 C14 C13 -0.5(2) . . . . ?
F2 C13 C14 F3 -0.10(19) . . . . ?
C12 C13 C14 F3 179.40(12) . . . . ?
F2 C13 C14 C15 -179.67(11) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_wl474
_database_code_depnum_ccdc_archive 'CCDC 2076297'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N5 O'
_chemical_formula_weight         361.44

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'
O O 0.0106 0.0060 '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                   14.645(5)
_cell_length_b                   12.306(3)
_cell_length_c                   10.398(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.185(10)
_cell_angle_gamma                90
_cell_volume                     1862.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    45926
_cell_measurement_theta_min      3.029
_cell_measurement_theta_max      27.541

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45926
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4280
_reflns_number_gt                2237
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0935P)²+0.0813P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.051(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4280
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
O1 O 0.28763(11) 0.29707(11) 0.00655(15) 0.0758(5) Uani 1 1 d . . . . .
N1 N 0.63695(12) 0.15053(12) 0.56685(17) 0.0577(5) Uani 1 1 d . . . . .
C1 C 0.81202(17) 0.44062(19) 0.8213(3) 0.0827(7) Uani 1 1 d . . . . .
H1A H 0.795720 0.505789 0.777562 0.099 Uiso 1 1 calc R U . . .
N2 N 0.57645(12) 0.13625(11) 0.46349(17) 0.0593(5) Uani 1 1 d . . . . .
C2 C 0.87142(19) 0.4434(2) 0.9325(3) 0.0947(8) Uani 1 1 d . . . . .
H2A H 0.894565 0.510507 0.964573 0.114 Uiso 1 1 calc R U . . .
N3 N 0.55958(11) 0.23519(11) 0.41205(16) 0.0545(5) Uani 1 1 d . . . . .
C3 C 0.89744(18) 0.3499(3) 0.9972(3) 0.0883(8) Uani 1 1 d . . . . .
H3A H 0.938634 0.352577 1.073002 0.106 Uiso 1 1 calc R U . . .
N4 N 0.68638(13) 0.43487(13) 0.59121(19) 0.0709(5) Uani 1 1 d . . . . .
C4 C 0.86301(17) 0.2523(2) 0.9508(2) 0.0829(7) Uani 1 1 d . . . . .
H4A H 0.880378 0.187817 0.995264 0.099 Uiso 1 1 calc R U . . .
N5 N 0.62381(13) 0.41917(13) 0.48395(19) 0.0690(5) Uani 1 1 d . . . . .
C5 C 0.80300(15) 0.2483(2) 0.8392(2) 0.0740(7) Uani 1 1 d . . . . .
H5A H 0.780512 0.180615 0.808274 0.089 Uiso 1 1 calc R U . . .
C6 C 0.77500(14) 0.34176(17) 0.7715(2) 0.0623(6) Uani 1 1 d . . . . .
C7 C 0.71019(14) 0.34108(15) 0.6552(2) 0.0601(6) Uani 1 1 d . . . . .
C8 C 0.65983(13) 0.25756(14) 0.58490(19) 0.0544(5) Uani 1 1 d . . . . .
C9 C 0.60972(13) 0.31172(15) 0.4847(2) 0.0559(5) Uani 1 1 d . . . . .
C10 C 0.49369(13) 0.24900(14) 0.30281(19) 0.0538(5) Uani 1 1 d . . . . .
C11 C 0.45588(14) 0.35113(15) 0.2780(2) 0.0606(6) Uani 1 1 d . . . . .
H11A H 0.475528 0.410596 0.330626 0.073 Uiso 1 1 calc R U . . .
C12 C 0.38970(15) 0.36425(15) 0.1761(2) 0.0647(6) Uani 1 1 d . . . . .
H12A H 0.364932 0.433668 0.157507 0.078 Uiso 1 1 calc R U . . .
C13 C 0.35844(14) 0.27633(15) 0.0996(2) 0.0587(5) Uani 1 1 d . . . . .
C14 C 0.39808(15) 0.17505(15) 0.1226(2) 0.0611(6) Uani 1 1 d . . . . .
H14A H 0.378816 0.115660 0.069662 0.073 Uiso 1 1 calc R U . . .
C15 C 0.46571(15) 0.16219(15) 0.2234(2) 0.0606(6) Uani 1 1 d . . . . .
H15A H 0.493328 0.093797 0.238791 0.073 Uiso 1 1 calc R U . . .
C16 C 0.24600(18) 0.20566(19) -0.0636(3) 0.0862(8) Uani 1 1 d . . . . .
H16A H 0.242150 0.143628 -0.005359 0.103 Uiso 1 1 calc R U . A 1
H16B H 0.282870 0.184263 -0.132707 0.103 Uiso 1 1 calc R U . A 1
C17 C 0.1505(3) 0.2397(3) -0.1207(4) 0.0783(10) Uani 0.685(3) 1 d . . P B 1
H17A H 0.119577 0.177220 -0.164629 0.094 Uiso 0.685(3) 1 calc R U P B 1
H17B H 0.114907 0.261561 -0.050458 0.094 Uiso 0.685(3) 1 calc R U P B 1
C18 C 0.1522(3) 0.3308(4) -0.2140(4) 0.0886(11) Uani 0.685(3) 1 d . . P B 1
H18A H 0.192436 0.311476 -0.279871 0.106 Uiso 0.685(3) 1 calc R U P B 1
H18B H 0.177962 0.395282 -0.168246 0.106 Uiso 0.685(3) 1 calc R U P B 1
C17A C 0.1951(6) 0.2585(7) -0.1974(8) 0.0783(10) Uani 0.315(3) 1 d . . P B 2
H17C H 0.229060 0.321609 -0.224551 0.094 Uiso 0.315(3) 1 calc R U P B 2
H17D H 0.189085 0.204898 -0.267497 0.094 Uiso 0.315(3) 1 calc R U P B 2
C18A C 0.1059(7) 0.2901(9) -0.1616(10) 0.0886(11) Uani 0.315(3) 1 d . . P B 2
H18C H 0.112865 0.334706 -0.083035 0.106 Uiso 0.315(3) 1 calc R U P B 2
H18D H 0.069507 0.225706 -0.145409 0.106 Uiso 0.315(3) 1 calc R U P B 2
C19 C 0.0568(2) 0.3583(3) -0.2806(3) 0.1195(11) Uani 1 1 d . . . . .
H19A H 0.037972 0.304808 -0.348174 0.143 Uiso 1 1 calc R U . B 1
H19B H 0.011482 0.358152 -0.217753 0.143 Uiso 1 1 calc R U . B 1
C20 C 0.0632(3) 0.4639(4) -0.3358(4) 0.1644(16) Uani 1 1 d . . . . .
H20A H 0.003523 0.485517 -0.377407 0.247 Uiso 1 1 calc R U . . .
H20B H 0.107104 0.462330 -0.399351 0.247 Uiso 1 1 calc R U . . .
H20C H 0.083457 0.515532 -0.268231 0.247 Uiso 1 1 calc R U . . .
C21 C 0.66807(17) 0.05382(16) 0.6394(2) 0.0735(7) Uani 1 1 d . . . . .
H21A H 0.657622 0.062796 0.729304 0.110 Uiso 1 1 calc R U . . .
H21B H 0.733121 0.043142 0.633567 0.110 Uiso 1 1 calc R U . . .
H21C H 0.634196 -0.008914 0.603567 0.110 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
O1 C13 1.364(2) . ?
O1 C16 1.440(3) . ?
N1 N2 1.329(2) . ?
N1 C8 1.367(2) . ?
N1 C21 1.455(2) . ?
C1 C2 1.370(3) . ?
C1 C6 1.408(3) . ?
C1 H1A 0.9400 . ?
N2 N3 1.342(2) . ?
C2 C3 1.366(4) . ?
C2 H2A 0.9400 . ?
N3 C9 1.370(2) . ?
N3 C10 1.419(3) . ?
C3 C4 1.370(4) . ?
C3 H3A 0.9400 . ?
N4 C7 1.359(2) . ?
N4 N5 1.379(2) . ?
C4 C5 1.379(3) . ?
C4 H4A 0.9400 . ?
N5 C9 1.338(2) . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9400 . ?
C6 C7 1.454(3) . ?
C7 C8 1.421(3) . ?
C8 C9 1.380(3) . ?
C10 C15 1.385(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.366(3) . ?
C11 H11A 0.9400 . ?
C12 C13 1.391(3) . ?
C12 H12A 0.9400 . ?
C13 C14 1.385(3) . ?
C14 C15 1.371(3) . ?
C14 H14A 0.9400 . ?
C15 H15A 0.9400 . ?
C16 C17 1.517(5) . ?
C16 C17A 1.640(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.485(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.529(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C17A C18A 1.450(15) . ?
C17A H17C 0.9800 . ?
C17A H17D 0.9800 . ?
C18A C19 1.600(10) . ?
C18A H18C 0.9800 . ?
C18A H18D 0.9800 . ?
C19 C20 1.428(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?

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
C13 O1 C16 117.47(17) . . ?
N2 N1 C8 111.75(15) . . ?
N2 N1 C21 117.07(16) . . ?
C8 N1 C21 131.17(19) . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
N1 N2 N3 106.29(15) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
N2 N3 C9 109.83(17) . . ?
N2 N3 C10 120.51(16) . . ?
C9 N3 C10 129.55(15) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C7 N4 N5 112.98(16) . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C9 N5 N4 102.90(15) . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 116.7(2) . . ?
C5 C6 C7 123.2(2) . . ?
C1 C6 C7 120.1(2) . . ?
N4 C7 C8 105.70(19) . . ?
N4 C7 C6 120.83(18) . . ?
C8 C7 C6 133.48(18) . . ?
N1 C8 C9 105.02(18) . . ?
N1 C8 C7 150.87(19) . . ?
C9 C8 C7 104.10(17) . . ?
N5 C9 N3 138.56(19) . . ?
N5 C9 C8 114.32(19) . . ?
N3 C9 C8 107.11(17) . . ?
C15 C10 C11 120.1(2) . . ?
C15 C10 N3 121.11(17) . . ?
C11 C10 N3 118.75(17) . . ?
C12 C11 C10 119.15(19) . . ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C11 C12 C13 120.94(18) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
O1 C13 C14 124.32(18) . . ?
O1 C13 C12 116.01(17) . . ?
C14 C13 C12 119.7(2) . . ?
C15 C14 C13 119.40(19) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C14 C15 C10 120.63(19) . . ?
C14 C15 H15A 119.7 . . ?
C10 C15 H15A 119.7 . . ?
O1 C16 C17 107.7(2) . . ?
O1 C16 C17A 104.4(3) . . ?
O1 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
O1 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C18 C17 C16 112.6(3) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 112.6(4) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18A C17A C16 103.2(7) . . ?
C18A C17A H17C 111.1 . . ?
C16 C17A H17C 111.1 . . ?
C18A C17A H17D 111.1 . . ?
C16 C17A H17D 111.1 . . ?
H17C C17A H17D 109.1 . . ?
C17A C18A C19 106.5(7) . . ?
C17A C18A H18C 110.4 . . ?
C19 C18A H18C 110.4 . . ?
C17A C18A H18D 110.4 . . ?
C19 C18A H18D 110.4 . . ?
H18C C18A H18D 108.6 . . ?
C20 C19 C18 106.6(3) . . ?
C20 C19 C18A 138.1(5) . . ?
C20 C19 H19A 110.4 . . ?
C18 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C18 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C8 N1 N2 N3 0.40(19) . . . . ?
C21 N1 N2 N3 -178.95(15) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
N1 N2 N3 C9 -0.36(19) . . . . ?
N1 N2 N3 C10 -176.89(15) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C7 N4 N5 C9 0.2(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -178.50(19) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
N5 N4 C7 C8 0.1(2) . . . . ?
N5 N4 C7 C6 -179.52(16) . . . . ?
C5 C6 C7 N4 -178.76(18) . . . . ?
C1 C6 C7 N4 1.8(3) . . . . ?
C5 C6 C7 C8 1.7(4) . . . . ?
C1 C6 C7 C8 -177.8(2) . . . . ?
N2 N1 C8 C9 -0.3(2) . . . . ?
C21 N1 C8 C9 179.0(2) . . . . ?
N2 N1 C8 C7 -179.5(3) . . . . ?
C21 N1 C8 C7 -0.3(5) . . . . ?
N4 C7 C8 N1 178.8(3) . . . . ?
C6 C7 C8 N1 -1.6(5) . . . . ?
N4 C7 C8 C9 -0.4(2) . . . . ?
C6 C7 C8 C9 179.2(2) . . . . ?
N4 N5 C9 N3 -179.1(2) . . . . ?
N4 N5 C9 C8 -0.5(2) . . . . ?
N2 N3 C9 N5 178.9(2) . . . . ?
C10 N3 C9 N5 -5.0(4) . . . . ?
N2 N3 C9 C8 0.2(2) . . . . ?
C10 N3 C9 C8 176.32(17) . . . . ?
N1 C8 C9 N5 -179.00(16) . . . . ?
C7 C8 C9 N5 0.6(2) . . . . ?
N1 C8 C9 N3 0.0(2) . . . . ?
C7 C8 C9 N3 179.65(15) . . . . ?
N2 N3 C10 C15 -19.6(3) . . . . ?
C9 N3 C10 C15 164.61(18) . . . . ?
N2 N3 C10 C11 158.99(16) . . . . ?
C9 N3 C10 C11 -16.8(3) . . . . ?
C15 C10 C11 C12 1.2(3) . . . . ?
N3 C10 C11 C12 -177.38(17) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C16 O1 C13 C14 6.1(3) . . . . ?
C16 O1 C13 C12 -172.43(19) . . . . ?
C11 C12 C13 O1 175.35(18) . . . . ?
C11 C12 C13 C14 -3.3(3) . . . . ?
O1 C13 C14 C15 -176.46(18) . . . . ?
C12 C13 C14 C15 2.1(3) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C11 C10 C15 C14 -2.5(3) . . . . ?
N3 C10 C15 C14 176.13(17) . . . . ?
C13 O1 C16 C17 158.5(2) . . . . ?
C13 O1 C16 C17A -159.0(3) . . . . ?
O1 C16 C17 C18 62.1(4) . . . . ?
C16 C17 C18 C19 174.8(3) . . . . ?
O1 C16 C17A C18A -86.8(6) . . . . ?
C16 C17A C18A C19 171.9(5) . . . . ?
C17 C18 C19 C20 163.1(4) . . . . ?
C17A C18A C19 C20 -74.5(10) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_wl470a
_database_code_depnum_ccdc_archive 'CCDC 2076299'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N5'
_chemical_formula_weight         331.42

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                   6.858(2)
_cell_length_b                   15.868(5)
_cell_length_c                   17.842(5)
_cell_angle_alpha                66.888(9)
_cell_angle_beta                 89.896(10)
_cell_angle_gamma                82.855(10)
_cell_volume                     1769.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    45126
_cell_measurement_theta_min      2.998
_cell_measurement_theta_max      27.708

_exptl_crystal_description       rod
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_T_max  0.7429
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45126
_diffrn_reflns_av_unetI/netI     0.1090
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         27.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8124
_reflns_number_gt                4582
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0985P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.058(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8124
_refine_ls_number_parameters     454
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1983
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_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 0.7592(3) 0.41603(14) 0.61482(11) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.7266(4) 0.67527(18) 0.34391(15) 0.0437(6) Uani 1 1 d . . . . .
H1 H 0.711647 0.648467 0.305445 0.052 Uiso 1 1 calc R U . . .
N2 N 0.7589(3) 0.32562(14) 0.65157(11) 0.0338(5) Uani 1 1 d . . . . .
C2 C 0.7262(4) 0.76946(19) 0.31661(17) 0.0499(7) Uani 1 1 d . . . . .
H2 H 0.709567 0.806901 0.259861 0.060 Uiso 1 1 calc R U . . .
N3 N 0.7470(3) 0.29617(13) 0.59086(11) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.7500(3) 0.80960(19) 0.37146(16) 0.0439(7) Uani 1 1 d . . . . .
H3 H 0.751328 0.874427 0.352790 0.053 Uiso 1 1 calc R U . . .
N4 N 0.7322(3) 0.47964(14) 0.39953(12) 0.0380(5) Uani 1 1 d . . . . .
C4 C 0.7718(4) 0.75464(19) 0.45335(17) 0.0458(7) Uani 1 1 d . . . . .
H4 H 0.787219 0.781697 0.491591 0.055 Uiso 1 1 calc R U . . .
N5 N 0.7284(3) 0.38512(15) 0.43698(12) 0.0387(5) Uani 1 1 d . . . . .
C5 C 0.7714(4) 0.66070(19) 0.48037(16) 0.0441(7) Uani 1 1 d . . . . .
H5 H 0.787340 0.623700 0.537224 0.053 Uiso 1 1 calc R U . . .
N6 N 0.6857(3) 0.06989(13) 1.08312(11) 0.0291(4) Uani 1 1 d . . . . .
C6 C 0.7484(3) 0.61882(16) 0.42635(14) 0.0320(5) Uani 1 1 d . . . . .
N7 N 0.6035(3) 0.15701(13) 1.06340(11) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.7445(3) 0.51946(17) 0.45371(14) 0.0325(6) Uani 1 1 d . . . . .
N8 N 0.5663(2) 0.19297(13) 0.98249(11) 0.0277(4) Uani 1 1 d . . . . .
C8 C 0.7486(3) 0.44691(16) 0.53229(13) 0.0303(5) Uani 1 1 d . . . . .
N9 N 0.7143(3) 0.02931(13) 0.90033(11) 0.0326(5) Uani 1 1 d . . . . .
C9 C 0.7394(3) 0.36872(17) 0.51642(13) 0.0316(5) Uani 1 1 d . . . . .
N10 N 0.6260(3) 0.11954(13) 0.87929(11) 0.0322(5) Uani 1 1 d . . . . .
C10 C 0.7487(3) 0.19989(16) 0.61019(14) 0.0314(5) Uani 1 1 d . . . . .
C11 C 0.7505(3) 0.13716(17) 0.69046(14) 0.0334(6) Uani 1 1 d . . . . .
H11 H 0.749851 0.157581 0.733899 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7532(3) 0.04434(17) 0.70643(15) 0.0351(6) Uani 1 1 d . . . . .
H12 H 0.754620 0.001230 0.761429 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7540(3) 0.01250(17) 0.64403(14) 0.0348(6) Uani 1 1 d . . . . .
C14 C 0.7516(3) 0.07766(17) 0.56440(15) 0.0383(6) Uani 1 1 d . . . . .
H14 H 0.751797 0.057422 0.520854 0.046 Uiso 1 1 calc R U . . .
C15 C 0.7490(3) 0.17091(18) 0.54626(14) 0.0378(6) Uani 1 1 d . . . . .
H15 H 0.747338 0.214129 0.491289 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7558(4) -0.08974(18) 0.66057(15) 0.0427(6) Uani 1 1 d . U . . .
C17 C 0.7653(5) -0.1528(2) 0.75107(17) 0.0657(9) Uani 1 1 d . U . . .
H17A H 0.654299 -0.132238 0.777284 0.098 Uiso 1 1 calc R U . . .
H17B H 0.758439 -0.216444 0.757210 0.098 Uiso 1 1 calc R U . . .
H17C H 0.889091 -0.150044 0.776832 0.098 Uiso 1 1 calc R U . . .
C18 C 0.9285(6) -0.1227(2) 0.6212(2) 0.0912(13) Uani 1 1 d . . . . .
H18A H 0.924280 -0.082736 0.563018 0.137 Uiso 1 1 calc R U . . .
H18B H 1.051781 -0.120049 0.647467 0.137 Uiso 1 1 calc R U . . .
H18C H 0.921130 -0.186449 0.627844 0.137 Uiso 1 1 calc R U . . .
C19 C 0.5663(6) -0.1021(2) 0.6220(2) 0.1008(14) Uani 1 1 d . . . . .
H19A H 0.451690 -0.081310 0.646292 0.151 Uiso 1 1 calc R U . . .
H19B H 0.559422 -0.065279 0.563082 0.151 Uiso 1 1 calc R U . . .
H19C H 0.567306 -0.167466 0.632176 0.151 Uiso 1 1 calc R U . . .
C20 C 0.7729(4) 0.46634(18) 0.66743(14) 0.0411(6) Uani 1 1 d . . . . .
H20A H 0.896354 0.493225 0.658904 0.062 Uiso 1 1 calc R U . . .
H20B H 0.769955 0.423741 0.724622 0.062 Uiso 1 1 calc R U . . .
H20C H 0.661564 0.515801 0.654057 0.062 Uiso 1 1 calc R U . . .
C21 C 0.8988(3) -0.16006(17) 0.96668(15) 0.0361(6) Uani 1 1 d . . . . .
H21 H 0.868912 -0.130433 0.909554 0.043 Uiso 1 1 calc R U . . .
C22 C 0.9858(4) -0.25126(18) 1.00027(17) 0.0443(7) Uani 1 1 d . . . . .
H22 H 1.013744 -0.283590 0.965747 0.053 Uiso 1 1 calc R U . . .
C23 C 1.0328(3) -0.29629(17) 1.08303(17) 0.0412(6) Uani 1 1 d . . . . .
H23 H 1.092801 -0.358875 1.105498 0.049 Uiso 1 1 calc R U . . .
C24 C 0.9911(3) -0.24860(17) 1.13200(16) 0.0409(6) Uani 1 1 d . . . . .
H24 H 1.022932 -0.278311 1.188976 0.049 Uiso 1 1 calc R U . . .
C25 C 0.9033(3) -0.15806(17) 1.09924(15) 0.0365(6) Uani 1 1 d . . . . .
H25 H 0.875016 -0.126460 1.134325 0.044 Uiso 1 1 calc R U . . .
C26 C 0.8549(3) -0.11154(16) 1.01603(14) 0.0290(5) Uani 1 1 d . . . . .
C27 C 0.7622(3) -0.01556(16) 0.98128(13) 0.0274(5) Uani 1 1 d . . . . .
C28 C 0.7025(3) 0.04850(15) 1.01647(13) 0.0258(5) Uani 1 1 d . . . . .
C29 C 0.6243(3) 0.12748(15) 0.95139(13) 0.0265(5) Uani 1 1 d . . . . .
C30 C 0.4866(3) 0.28749(15) 0.94252(13) 0.0279(5) Uani 1 1 d . . . . .
C31 C 0.4313(3) 0.33900(17) 0.98819(15) 0.0355(6) Uani 1 1 d . . . . .
H31 H 0.446611 0.311566 1.046049 0.043 Uiso 1 1 calc R U . . .
C32 C 0.3540(4) 0.43025(17) 0.94857(15) 0.0388(6) Uani 1 1 d . . . . .
H32 H 0.317060 0.465471 0.980041 0.047 Uiso 1 1 calc R U . . .
C33 C 0.3275(3) 0.47337(16) 0.86341(14) 0.0335(6) Uani 1 1 d . . . . .
C34 C 0.3856(3) 0.41903(16) 0.82003(14) 0.0325(5) Uani 1 1 d . . . . .
H34 H 0.370899 0.446032 0.762151 0.039 Uiso 1 1 calc R U . . .
C35 C 0.4636(3) 0.32737(16) 0.85841(14) 0.0308(5) Uani 1 1 d . . . . .
H35 H 0.501382 0.291839 0.827272 0.037 Uiso 1 1 calc R U . . .
C36 C 0.2401(4) 0.57447(17) 0.81860(16) 0.0408(6) Uani 1 1 d . . . . .
C37 C 0.1681(5) 0.6188(2) 0.87677(18) 0.0615(9) Uani 1 1 d . . . . .
H37A H 0.113409 0.683499 0.845470 0.092 Uiso 1 1 calc R U . . .
H37B H 0.066068 0.585463 0.909576 0.092 Uiso 1 1 calc R U . . .
H37C H 0.278383 0.616231 0.912825 0.092 Uiso 1 1 calc R U . . .
C38 C 0.0654(4) 0.58057(19) 0.76181(17) 0.0495(7) Uani 1 1 d . . . . .
H38A H 0.109815 0.552125 0.723846 0.074 Uiso 1 1 calc R U . . .
H38B H -0.037625 0.547863 0.794489 0.074 Uiso 1 1 calc R U . . .
H38C H 0.012709 0.645599 0.730949 0.074 Uiso 1 1 calc R U . . .
C39 C 0.3940(5) 0.6287(2) 0.7653(2) 0.0681(9) Uani 1 1 d . . . . .
H39A H 0.440615 0.600120 0.727716 0.102 Uiso 1 1 calc R U . . .
H39B H 0.334924 0.692721 0.733999 0.102 Uiso 1 1 calc R U . . .
H39C H 0.505112 0.628133 0.800065 0.102 Uiso 1 1 calc R U . . .
C40 C 0.7360(4) 0.01480(18) 1.16919(14) 0.0446(7) Uani 1 1 d . . . . .
H40A H 0.877022 -0.008241 1.176709 0.067 Uiso 1 1 calc R U . . .
H40B H 0.660452 -0.037600 1.188408 0.067 Uiso 1 1 calc R U . . .
H40C H 0.704588 0.053114 1.200446 0.067 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 N2 1.323(3) . ?
N1 C8 1.356(3) . ?
N1 C20 1.461(3) . ?
C1 C2 1.378(4) . ?
C1 C6 1.386(3) . ?
C1 H1 0.9500 . ?
N2 N3 1.344(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
N3 C9 1.370(3) . ?
N3 C10 1.426(3) . ?
C3 C4 1.373(4) . ?
C3 H3 0.9500 . ?
N4 C7 1.354(3) . ?
N4 N5 1.385(3) . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
N5 C9 1.337(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
N6 N7 1.333(3) . ?
N6 C28 1.360(3) . ?
N6 C40 1.454(3) . ?
C6 C7 1.460(3) . ?
N7 N8 1.339(2) . ?
C7 C8 1.420(3) . ?
N8 C29 1.377(3) . ?
N8 C30 1.419(3) . ?
C8 C9 1.385(3) . ?
N9 C27 1.355(3) . ?
N9 N10 1.386(3) . ?
N10 C29 1.341(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 C16 1.529(4) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C18 1.516(4) . ?
C16 C17 1.526(4) . ?
C16 C19 1.540(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.384(3) . ?
C21 C26 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.372(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.459(3) . ?
C27 C28 1.411(3) . ?
C28 C29 1.378(3) . ?
C30 C35 1.381(3) . ?
C30 C31 1.386(3) . ?
C31 C32 1.373(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.401(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.392(3) . ?
C33 C36 1.526(3) . ?
C34 C35 1.377(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.517(4) . ?
C36 C39 1.529(4) . ?
C36 C38 1.540(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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 C8 112.97(18) . . ?
N2 N1 C20 116.75(18) . . ?
C8 N1 C20 130.3(2) . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
N1 N2 N3 105.16(17) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N2 N3 C9 110.70(19) . . ?
N2 N3 C10 119.39(19) . . ?
C9 N3 C10 129.9(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C7 N4 N5 112.73(19) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C9 N5 N4 103.09(19) . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N7 N6 C28 111.67(18) . . ?
N7 N6 C40 116.67(18) . . ?
C28 N6 C40 131.64(19) . . ?
C1 C6 C5 117.4(2) . . ?
C1 C6 C7 120.2(2) . . ?
C5 C6 C7 122.3(2) . . ?
N6 N7 N8 106.13(16) . . ?
N4 C7 C8 106.0(2) . . ?
N4 C7 C6 121.1(2) . . ?
C8 C7 C6 132.8(2) . . ?
N7 N8 C29 110.04(17) . . ?
N7 N8 C30 119.31(17) . . ?
C29 N8 C30 130.58(18) . . ?
N1 C8 C9 104.9(2) . . ?
N1 C8 C7 151.0(2) . . ?
C9 C8 C7 104.1(2) . . ?
C27 N9 N10 112.98(18) . . ?
N5 C9 N3 139.7(2) . . ?
N5 C9 C8 114.0(2) . . ?
N3 C9 C8 106.2(2) . . ?
C29 N10 N9 102.30(17) . . ?
C11 C10 C15 121.0(2) . . ?
C11 C10 N3 121.0(2) . . ?
C15 C10 N3 118.0(2) . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 117.4(2) . . ?
C14 C13 C16 120.2(2) . . ?
C12 C13 C16 122.4(2) . . ?
C15 C14 C13 122.4(2) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C10 118.5(2) . . ?
C14 C15 H15 120.8 . . ?
C10 C15 H15 120.8 . . ?
C18 C16 C17 108.6(3) . . ?
C18 C16 C13 110.2(2) . . ?
C17 C16 C13 113.8(2) . . ?
C18 C16 C19 107.5(3) . . ?
C17 C16 C19 107.3(3) . . ?
C13 C16 C19 109.2(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C26 C21 H21 119.8 . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 120.5(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 121.7(2) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C21 C26 C25 117.4(2) . . ?
C21 C26 C27 120.8(2) . . ?
C25 C26 C27 121.8(2) . . ?
N9 C27 C28 105.98(19) . . ?
N9 C27 C26 121.6(2) . . ?
C28 C27 C26 132.4(2) . . ?
N6 C28 C29 105.64(19) . . ?
N6 C28 C27 150.1(2) . . ?
C29 C28 C27 104.24(19) . . ?
N10 C29 N8 139.0(2) . . ?
N10 C29 C28 114.5(2) . . ?
N8 C29 C28 106.51(18) . . ?
C35 C30 C31 120.4(2) . . ?
C35 C30 N8 119.79(19) . . ?
C31 C30 N8 119.8(2) . . ?
C32 C31 C30 119.0(2) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C31 C32 C33 122.4(2) . . ?
C31 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
C34 C33 C32 116.6(2) . . ?
C34 C33 C36 120.4(2) . . ?
C32 C33 C36 123.0(2) . . ?
C35 C34 C33 122.1(2) . . ?
C35 C34 H34 119.0 . . ?
C33 C34 H34 119.0 . . ?
C34 C35 C30 119.5(2) . . ?
C34 C35 H35 120.3 . . ?
C30 C35 H35 120.3 . . ?
C37 C36 C33 112.3(2) . . ?
C37 C36 C39 109.4(2) . . ?
C33 C36 C39 109.7(2) . . ?
C37 C36 C38 108.6(2) . . ?
C33 C36 C38 109.2(2) . . ?
C39 C36 C38 107.6(2) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N6 C40 H40A 109.5 . . ?
N6 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N6 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
C8 N1 N2 N3 -0.2(2) . . . . ?
C20 N1 N2 N3 -179.51(17) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
N1 N2 N3 C9 -0.2(2) . . . . ?
N1 N2 N3 C10 178.37(17) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C7 N4 N5 C9 -0.1(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
C28 N6 N7 N8 -0.1(2) . . . . ?
C40 N6 N7 N8 -178.59(18) . . . . ?
N5 N4 C7 C8 -0.2(2) . . . . ?
N5 N4 C7 C6 -179.40(18) . . . . ?
C1 C6 C7 N4 4.2(3) . . . . ?
C5 C6 C7 N4 -176.5(2) . . . . ?
C1 C6 C7 C8 -174.8(2) . . . . ?
C5 C6 C7 C8 4.5(4) . . . . ?
N6 N7 N8 C29 0.5(2) . . . . ?
N6 N7 N8 C30 -176.88(17) . . . . ?
N2 N1 C8 C9 0.5(2) . . . . ?
C20 N1 C8 C9 179.7(2) . . . . ?
N2 N1 C8 C7 -178.2(3) . . . . ?
C20 N1 C8 C7 0.9(5) . . . . ?
N4 C7 C8 N1 179.1(3) . . . . ?
C6 C7 C8 N1 -1.8(5) . . . . ?
N4 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C8 C9 179.5(2) . . . . ?
N4 N5 C9 N3 -178.6(3) . . . . ?
N4 N5 C9 C8 0.4(2) . . . . ?
N2 N3 C9 N5 179.5(3) . . . . ?
C10 N3 C9 N5 1.2(4) . . . . ?
N2 N3 C9 C8 0.5(2) . . . . ?
C10 N3 C9 C8 -177.86(19) . . . . ?
N1 C8 C9 N5 -179.90(17) . . . . ?
C7 C8 C9 N5 -0.5(2) . . . . ?
N1 C8 C9 N3 -0.6(2) . . . . ?
C7 C8 C9 N3 178.81(17) . . . . ?
C27 N9 N10 C29 0.5(2) . . . . ?
N2 N3 C10 C11 3.9(3) . . . . ?
C9 N3 C10 C11 -177.9(2) . . . . ?
N2 N3 C10 C15 -175.94(19) . . . . ?
C9 N3 C10 C15 2.3(3) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
N3 C10 C11 C12 -179.64(19) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 C13 C16 -179.6(2) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C16 C13 C14 C15 179.7(2) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
N3 C10 C15 C14 179.68(19) . . . . ?
C14 C13 C16 C18 55.8(3) . . . . ?
C12 C13 C16 C18 -124.7(3) . . . . ?
C14 C13 C16 C17 178.1(2) . . . . ?
C12 C13 C16 C17 -2.4(3) . . . . ?
C14 C13 C16 C19 -62.1(3) . . . . ?
C12 C13 C16 C19 117.4(3) . . . . ?
C26 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C22 C21 C26 C27 -179.7(2) . . . . ?
C24 C25 C26 C21 -0.1(3) . . . . ?
C24 C25 C26 C27 -179.9(2) . . . . ?
N10 N9 C27 C28 -0.1(2) . . . . ?
N10 N9 C27 C26 179.40(18) . . . . ?
C21 C26 C27 N9 0.6(3) . . . . ?
C25 C26 C27 N9 -179.6(2) . . . . ?
C21 C26 C27 C28 179.9(2) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
N7 N6 C28 C29 -0.4(2) . . . . ?
C40 N6 C28 C29 177.8(2) . . . . ?
N7 N6 C28 C27 179.2(3) . . . . ?
C40 N6 C28 C27 -2.6(5) . . . . ?
N9 C27 C28 N6 179.9(3) . . . . ?
C26 C27 C28 N6 0.6(5) . . . . ?
N9 C27 C28 C29 -0.4(2) . . . . ?
C26 C27 C28 C29 -179.8(2) . . . . ?
N9 N10 C29 N8 179.0(2) . . . . ?
N9 N10 C29 C28 -0.9(2) . . . . ?
N7 N8 C29 N10 179.3(2) . . . . ?
C30 N8 C29 N10 -3.6(4) . . . . ?
N7 N8 C29 C28 -0.8(2) . . . . ?
C30 N8 C29 C28 176.23(19) . . . . ?
N6 C28 C29 N10 -179.36(17) . . . . ?
C27 C28 C29 N10 0.8(2) . . . . ?
N6 C28 C29 N8 0.7(2) . . . . ?
C27 C28 C29 N8 -179.07(16) . . . . ?
N7 N8 C30 C35 174.40(19) . . . . ?
C29 N8 C30 C35 -2.4(3) . . . . ?
N7 N8 C30 C31 -6.0(3) . . . . ?
C29 N8 C30 C31 177.2(2) . . . . ?
C35 C30 C31 C32 -0.2(3) . . . . ?
N8 C30 C31 C32 -179.8(2) . . . . ?
C30 C31 C32 C33 0.4(4) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C31 C32 C33 C36 179.5(2) . . . . ?
C32 C33 C34 C35 0.5(3) . . . . ?
C36 C33 C34 C35 -179.5(2) . . . . ?
C33 C34 C35 C30 -0.3(3) . . . . ?
C31 C30 C35 C34 0.2(3) . . . . ?
N8 C30 C35 C34 179.78(19) . . . . ?
C34 C33 C36 C37 174.4(2) . . . . ?
C32 C33 C36 C37 -5.7(3) . . . . ?
C34 C33 C36 C39 -63.7(3) . . . . ?
C32 C33 C36 C39 116.2(3) . . . . ?
C34 C33 C36 C38 53.9(3) . . . . ?
C32 C33 C36 C38 -126.1(2) . . . . ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.119



####################################################################### 
# 
# 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_wl487a
_database_code_depnum_ccdc_archive 'CCDC 2076304'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N5'
_chemical_formula_weight         283.38

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      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                   13.043(4)
_cell_length_b                   16.924(5)
_cell_length_c                   7.147(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.239(17)
_cell_angle_gamma                90
_cell_volume                     1564.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    21722
_cell_measurement_theta_min      3.323
_cell_measurement_theta_max      3.323

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21722
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.323
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3569
_reflns_number_gt                2228
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0775P)²+0.5226P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3569
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1883
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.51788(13) 0.85415(9) 0.4856(2) 0.0362(4) Uani 1 1 d . . . . .
C1 C 0.39645(18) 0.57666(12) 0.3765(3) 0.0446(6) Uani 1 1 d . . . . .
H1A H 0.453277 0.544471 0.425338 0.054 Uiso 1 1 calc R U . . .
N2 N 0.59743(14) 0.89597(11) 0.5682(2) 0.0431(5) Uani 1 1 d . . . . .
C2 C 0.30571(19) 0.54128(13) 0.2989(3) 0.0484(6) Uani 1 1 d . . . . .
H2A H 0.300583 0.485286 0.296094 0.058 Uiso 1 1 calc R U . . .
N3 N 0.66760(13) 0.84308(11) 0.6415(2) 0.0421(5) Uani 1 1 d . . . . .
C3 C 0.22257(19) 0.58641(13) 0.2254(3) 0.0504(6) Uani 1 1 d . . . . .
H3A H 0.159971 0.561978 0.172504 0.060 Uiso 1 1 calc R U . . .
N4 N 0.58183(13) 0.64941(10) 0.5575(2) 0.0408(5) Uani 1 1 d . . . . .
C4 C 0.23137(18) 0.66802(14) 0.2296(4) 0.0554(6) Uani 1 1 d . . . . .
H4A H 0.174732 0.699725 0.177590 0.066 Uiso 1 1 calc R U . . .
N5 N 0.66458(13) 0.69339(11) 0.6398(2) 0.0435(5) Uani 1 1 d . . . . .
C5 C 0.32193(17) 0.70361(13) 0.3088(3) 0.0464(6) Uani 1 1 d . . . . .
H5A H 0.326291 0.759643 0.311154 0.056 Uiso 1 1 calc R U . . .
C6 C 0.40671(15) 0.65935(11) 0.3850(2) 0.0348(5) Uani 1 1 d . . . . .
C7 C 0.50285(15) 0.69511(12) 0.4755(2) 0.0344(5) Uani 1 1 d . . . . .
C8 C 0.53507(15) 0.77474(11) 0.5044(2) 0.0336(5) Uani 1 1 d . . . . .
C9 C 0.63258(16) 0.76798(12) 0.6051(3) 0.0374(5) Uani 1 1 d . . . . .
C10 C 0.76400(18) 0.86971(16) 0.7533(3) 0.0544(6) Uani 1 1 d . . . . .
H10A H 0.767734 0.847439 0.882045 0.065 Uiso 1 1 calc R U . A 1
H10B H 0.762775 0.928010 0.764133 0.065 Uiso 1 1 calc R U . A 1
C12 C 0.8723(2) 0.8759(2) 0.4854(4) 0.0801(10) Uani 1 1 d . . . . .
H12A H 0.815915 0.852242 0.397430 0.096 Uiso 1 1 calc R U . B 1
H12B H 0.856351 0.933007 0.490124 0.096 Uiso 1 1 calc R U . B 1
C13 C 0.9612(2) 0.8711(2) 0.3909(5) 0.0940(12) Uani 1 1 d . . . . .
H13A H 1.019159 0.888578 0.484557 0.113 Uiso 1 1 calc R U . C 1
H13B H 0.972074 0.813865 0.372055 0.113 Uiso 1 1 calc R U . C 1
C15 C 1.0802(3) 0.8860(2) 0.1420(6) 0.1080(13) Uani 1 1 d . . . . .
H15A H 1.082730 0.914795 0.023654 0.162 Uiso 1 1 calc R U . D 1
H15B H 1.139378 0.901243 0.233143 0.162 Uiso 1 1 calc R U . D 1
H15C H 1.082679 0.829069 0.118149 0.162 Uiso 1 1 calc R U . D 1
C16 C 0.42911(17) 0.89804(12) 0.3931(3) 0.0420(5) Uani 1 1 d . . . . .
H16A H 0.414204 0.880849 0.261504 0.063 Uiso 1 1 calc R U . . .
H16B H 0.444814 0.954684 0.396999 0.063 Uiso 1 1 calc R U . . .
H16C H 0.368793 0.888001 0.458665 0.063 Uiso 1 1 calc R U . . .
C11 C 0.8574(3) 0.8458(3) 0.6692(5) 0.0590(12) Uani 0.684(5) 1 d . . P E 1
H11A H 0.918442 0.861331 0.758297 0.071 Uiso 0.684(5) 1 calc R U P E 1
H11B H 0.857596 0.787378 0.661746 0.071 Uiso 0.684(5) 1 calc R U P E 1
C14 C 0.9787(3) 0.9065(3) 0.2224(6) 0.0714(14) Uani 0.684(5) 1 d . . P E 1
H14A H 0.976770 0.964427 0.240245 0.086 Uiso 0.684(5) 1 calc R U P E 1
H14B H 0.920321 0.892570 0.125757 0.086 Uiso 0.684(5) 1 calc R U P E 1
C11A C 0.8373(5) 0.9071(5) 0.6314(9) 0.043(2) Uani 0.316(5) 1 d . . P E 2
H11C H 0.804200 0.957385 0.585863 0.051 Uiso 0.316(5) 1 calc R U P E 2
H11D H 0.899285 0.921978 0.718836 0.051 Uiso 0.316(5) 1 calc R U P E 2
C14A C 1.0102(7) 0.8454(5) 0.2491(12) 0.060(2) Uani 0.316(5) 1 d . . P E 2
H14C H 0.954618 0.825481 0.153587 0.072 Uiso 0.316(5) 1 calc R U P E 2
H14D H 1.048773 0.798067 0.299835 0.072 Uiso 0.316(5) 1 calc R U P E 2


_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 1.331(2) . ?
N1 C8 1.366(2) . ?
N1 C16 1.462(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.406(3) . ?
C1 H1A 0.9500 . ?
N2 N3 1.339(2) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9500 . ?
N3 C9 1.364(3) . ?
N3 C10 1.473(3) . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
N4 C7 1.360(2) . ?
N4 N5 1.380(2) . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9500 . ?
N5 C9 1.343(3) . ?
C5 C6 1.389(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.467(3) . ?
C7 C8 1.419(3) . ?
C8 C9 1.385(3) . ?
C10 C11 1.481(5) . ?
C10 C11A 1.511(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C11A 1.302(7) . ?
C12 C13 1.416(4) . ?
C12 C11 1.444(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14A 1.337(8) . ?
C13 C14 1.389(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C14A 1.438(8) . ?
C15 C14 1.547(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?

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 C8 111.74(16) . . ?
N2 N1 C16 117.34(16) . . ?
C8 N1 C16 130.92(17) . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
N1 N2 N3 105.92(16) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
N2 N3 C9 110.63(17) . . ?
N2 N3 C10 120.17(18) . . ?
C9 N3 C10 129.11(19) . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C7 N4 N5 112.71(17) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C9 N5 N4 102.71(16) . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 116.94(19) . . ?
C5 C6 C7 122.99(18) . . ?
C1 C6 C7 120.06(18) . . ?
N4 C7 C8 106.43(17) . . ?
N4 C7 C6 120.94(18) . . ?
C8 C7 C6 132.60(18) . . ?
N1 C8 C9 105.12(17) . . ?
N1 C8 C7 151.39(19) . . ?
C9 C8 C7 103.47(17) . . ?
N5 C9 N3 138.7(2) . . ?
N5 C9 C8 114.67(18) . . ?
N3 C9 C8 106.59(18) . . ?
N3 C10 C11 112.7(2) . . ?
N3 C10 C11A 112.0(3) . . ?
N3 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N3 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11A C12 C13 142.8(4) . . ?
C13 C12 C11 128.7(3) . . ?
C13 C12 H12A 105.1 . . ?
C11 C12 H12A 105.1 . . ?
C13 C12 H12B 105.1 . . ?
C11 C12 H12B 105.1 . . ?
H12A C12 H12B 105.9 . . ?
C14A C13 C12 151.5(5) . . ?
C14 C13 C12 128.5(4) . . ?
C14 C13 H13A 105.2 . . ?
C12 C13 H13A 105.2 . . ?
C14 C13 H13B 105.2 . . ?
C12 C13 H13B 105.2 . . ?
H13A C13 H13B 105.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11A 107.6 . . ?
C10 C11 H11A 107.6 . . ?
C12 C11 H11B 107.6 . . ?
C10 C11 H11B 107.6 . . ?
H11A C11 H11B 107.0 . . ?
C13 C14 C15 117.9(4) . . ?
C13 C14 H14A 107.8 . . ?
C15 C14 H14A 107.8 . . ?
C13 C14 H14B 107.8 . . ?
C15 C14 H14B 107.8 . . ?
H14A C14 H14B 107.2 . . ?
C12 C11A C10 127.1(6) . . ?
C12 C11A H11C 105.5 . . ?
C10 C11A H11C 105.5 . . ?
C12 C11A H11D 105.5 . . ?
C10 C11A H11D 105.5 . . ?
H11C C11A H11D 106.1 . . ?
C13 C14A C15 130.1(7) . . ?
C13 C14A H14C 104.7 . . ?
C15 C14A H14C 104.7 . . ?
C13 C14A H14D 104.7 . . ?
C15 C14A H14D 104.7 . . ?
H14C C14A H14D 105.7 . . ?

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
C8 N1 N2 N3 0.1(2) . . . . ?
C16 N1 N2 N3 179.98(15) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
N1 N2 N3 C9 0.1(2) . . . . ?
N1 N2 N3 C10 -176.60(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C7 N4 N5 C9 0.2(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 177.51(18) . . . . ?
N5 N4 C7 C8 0.2(2) . . . . ?
N5 N4 C7 C6 -178.27(15) . . . . ?
C5 C6 C7 N4 176.31(18) . . . . ?
C1 C6 C7 N4 -2.2(3) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C1 C6 C7 C8 179.85(19) . . . . ?
N2 N1 C8 C9 -0.3(2) . . . . ?
C16 N1 C8 C9 179.88(18) . . . . ?
N2 N1 C8 C7 177.9(3) . . . . ?
C16 N1 C8 C7 -1.9(5) . . . . ?
N4 C7 C8 N1 -178.7(3) . . . . ?
C6 C7 C8 N1 -0.5(5) . . . . ?
N4 C7 C8 C9 -0.48(19) . . . . ?
C6 C7 C8 C9 177.71(19) . . . . ?
N4 N5 C9 N3 178.6(2) . . . . ?
N4 N5 C9 C8 -0.6(2) . . . . ?
N2 N3 C9 N5 -179.5(2) . . . . ?
C10 N3 C9 N5 -3.2(4) . . . . ?
N2 N3 C9 C8 -0.3(2) . . . . ?
C10 N3 C9 C8 176.03(18) . . . . ?
N1 C8 C9 N5 179.77(15) . . . . ?
C7 C8 C9 N5 0.7(2) . . . . ?
N1 C8 C9 N3 0.3(2) . . . . ?
C7 C8 C9 N3 -178.75(15) . . . . ?
N2 N3 C10 C11 -119.0(3) . . . . ?
C9 N3 C10 C11 65.0(3) . . . . ?
N2 N3 C10 C11A -72.4(4) . . . . ?
C9 N3 C10 C11A 111.6(4) . . . . ?
C11A C12 C13 C14A -178.5(11) . . . . ?
C11 C12 C13 C14 -173.2(4) . . . . ?
C13 C12 C11 C10 169.6(3) . . . . ?
N3 C10 C11 C12 62.8(4) . . . . ?
C12 C13 C14 C15 -175.3(4) . . . . ?
C13 C12 C11A C10 -143.2(6) . . . . ?
N3 C10 C11A C12 -55.1(8) . . . . ?
C12 C13 C14A C15 138.4(9) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.046


