# 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. 
# 
#######################################################################

data_wl419
_database_code_depnum_ccdc_archive 'CCDC 2020697'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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 H21 N3 O2'
_chemical_formula_weight         323.39

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'
O O 0.0106 0.0060 '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                   7.554(5)
_cell_length_b                   7.800(5)
_cell_length_c                   15.305(10)
_cell_angle_alpha                96.293(19)
_cell_angle_beta                 90.202(18)
_cell_angle_gamma                99.553(18)
_cell_volume                     883.7(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    16545
_cell_measurement_theta_min      2.735
_cell_measurement_theta_max      27.464

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.996
_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            16545
_diffrn_reflns_av_unetI/netI     0.1033
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.735
_diffrn_reflns_theta_max         27.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3976
_reflns_number_gt                2090
_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)+(0.0722P)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       0.062(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3976
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
C1 C 0.5665(3) 0.0556(3) 0.20553(14) 0.0387(6) Uani 1 1 d . . . . .
H1A H 0.659629 0.145109 0.230202 0.046 Uiso 1 1 calc R U . . .
O1 O 0.4999(2) 0.2278(2) 0.37140(10) 0.0545(5) Uani 1 1 d . . . . .
N1 N 0.8005(2) 0.8709(2) 0.39726(11) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.5808(3) -0.0225(3) 0.12100(14) 0.0426(6) Uani 1 1 d . . . . .
H2A H 0.683962 0.013527 0.088021 0.051 Uiso 1 1 calc R U . . .
N2 N 0.8875(2) 0.8017(2) 0.33241(11) 0.0371(5) Uani 1 1 d . . . . .
O2 O 0.298(5) -0.009(2) 0.3940(9) 0.060(5) Uani 0.50(8) 1 d . . P A 1
O2A O 0.256(3) 0.050(8) 0.3867(13) 0.078(8) Uani 0.50(8) 1 d . . P A 2
C3 C 0.4470(3) -0.1518(3) 0.08411(14) 0.0421(6) Uani 1 1 d . . . . .
H3A H 0.456919 -0.203925 0.025647 0.051 Uiso 1 1 calc R U . . .
N3 N 0.8203(2) 0.6328(2) 0.32638(10) 0.0326(4) Uani 1 1 d . . . . .
C4 C 0.2982(3) -0.2055(3) 0.13244(14) 0.0441(6) Uani 1 1 d . . . . .
H4A H 0.205428 -0.295014 0.107462 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2848(3) -0.1290(3) 0.21682(14) 0.0442(6) Uani 1 1 d . . . . .
H5A H 0.182879 -0.167811 0.250070 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4172(3) 0.0041(3) 0.25458(13) 0.0357(5) Uani 1 1 d . . . . .
C7 C 0.3956(3) 0.0889(3) 0.34641(14) 0.0445(6) Uani 1 1 d . . . . .
C8 C 0.6792(3) 0.7519(3) 0.43196(14) 0.0428(6) Uani 1 1 d . . . . .
H8A H 0.601201 0.772842 0.479029 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6916(3) 0.5954(3) 0.38569(13) 0.0399(6) Uani 1 1 d . . . . .
H9A H 0.624342 0.484121 0.393396 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8999(3) 0.5177(2) 0.26364(13) 0.0316(5) Uani 1 1 d . . . . .
C11 C 1.0555(3) 0.4611(3) 0.28884(13) 0.0356(5) Uani 1 1 d . . . . .
C12 C 1.1338(3) 0.3577(3) 0.22570(14) 0.0416(6) Uani 1 1 d . . . . .
H12A H 1.238914 0.314743 0.241117 0.050 Uiso 1 1 calc R U . . .
C13 C 1.0638(3) 0.3152(3) 0.14135(14) 0.0387(6) Uani 1 1 d . . . . .
C14 C 0.9089(3) 0.3754(3) 0.11957(13) 0.0373(6) Uani 1 1 d . . . . .
H14A H 0.861175 0.347170 0.061289 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8211(3) 0.4755(3) 0.18002(13) 0.0351(5) Uani 1 1 d . . . . .
C16 C 1.1401(3) 0.5134(3) 0.37879(14) 0.0519(7) Uani 1 1 d . . . . .
H16A H 1.233188 0.442775 0.387440 0.078 Uiso 1 1 calc R U . . .
H16B H 1.048105 0.494276 0.423319 0.078 Uiso 1 1 calc R U . . .
H16C H 1.194048 0.637478 0.384336 0.078 Uiso 1 1 calc R U . . .
C17 C 1.1578(4) 0.2094(3) 0.07317(16) 0.0592(7) Uani 1 1 d . . . . .
H17A H 1.101349 0.207899 0.015278 0.089 Uiso 1 1 calc R U . . .
H17B H 1.148225 0.089370 0.088286 0.089 Uiso 1 1 calc R U . . .
H17C H 1.284678 0.262292 0.071755 0.089 Uiso 1 1 calc R U . . .
C18 C 0.6493(3) 0.5340(3) 0.15760(16) 0.0565(7) Uani 1 1 d . . . . .
H18A H 0.657164 0.658735 0.177811 0.085 Uiso 1 1 calc R U . . .
H18B H 0.549623 0.466760 0.186540 0.085 Uiso 1 1 calc R U . . .
H18C H 0.628565 0.514904 0.093769 0.085 Uiso 1 1 calc R U . . .
C19 C 0.8457(3) 1.0608(3) 0.42344(15) 0.0468(6) Uani 1 1 d . . . . .
H19A H 0.834377 1.084751 0.487205 0.070 Uiso 1 1 calc R U . . .
H19B H 0.763374 1.121022 0.393439 0.070 Uiso 1 1 calc R U . . .
H19C H 0.969309 1.102853 0.407095 0.070 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 1.381(3) . ?
C1 C6 1.385(3) . ?
O1 C7 1.251(3) . ?
N1 N2 1.309(2) . ?
N1 C8 1.346(3) . ?
N1 C19 1.474(3) . ?
C2 C3 1.375(3) . ?
N2 N3 1.324(2) . ?
O2 C7 1.262(16) . ?
O2A C7 1.234(15) . ?
C3 C4 1.379(3) . ?
N3 C9 1.351(3) . ?
N3 C10 1.443(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.508(3) . ?
C8 C9 1.359(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.388(3) . ?
C11 C16 1.501(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.383(3) . ?
C13 C17 1.512(3) . ?
C14 C15 1.387(3) . ?
C15 C18 1.496(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.4(2) . . ?
N2 N1 C8 112.79(17) . . ?
N2 N1 C19 118.45(17) . . ?
C8 N1 C19 128.76(19) . . ?
C3 C2 C1 120.6(2) . . ?
N1 N2 N3 103.93(16) . . ?
C2 C3 C4 119.6(2) . . ?
N2 N3 C9 112.54(16) . . ?
N2 N3 C10 117.18(16) . . ?
C9 N3 C10 130.15(18) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 C6 121.4(2) . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 121.8(2) . . ?
C5 C6 C7 119.99(19) . . ?
O2A C7 O1 119.3(18) . . ?
O1 C7 O2 127.1(7) . . ?
O2A C7 C6 120.8(11) . . ?
O1 C7 C6 117.5(2) . . ?
O2 C7 C6 113.8(7) . . ?
N1 C8 C9 105.75(19) . . ?
N3 C9 C8 104.97(19) . . ?
C11 C10 C15 123.51(19) . . ?
C11 C10 N3 118.15(19) . . ?
C15 C10 N3 118.3(2) . . ?
C12 C11 C10 116.8(2) . . ?
C12 C11 C16 121.0(2) . . ?
C10 C11 C16 122.2(2) . . ?
C13 C12 C11 122.1(2) . . ?
C12 C13 C14 118.8(2) . . ?
C12 C13 C17 120.5(2) . . ?
C14 C13 C17 120.6(2) . . ?
C13 C14 C15 122.2(2) . . ?
C14 C15 C10 116.6(2) . . ?
C14 C15 C18 122.2(2) . . ?
C10 C15 C18 121.2(2) . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.235
_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_wl368a
_database_code_depnum_ccdc_archive 'CCDC 2104505'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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            'C12 H15 N3 O'
_chemical_formula_weight         217.27

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/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                   10.765(4)
_cell_length_b                   8.899(3)
_cell_length_c                   37.044(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.947(13)
_cell_angle_gamma                90
_cell_volume                     3536(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    126978
_cell_measurement_theta_min      2.974
_cell_measurement_theta_max      30.090

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7104
_exptl_absorpt_correction_T_max  0.7342
_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            126978
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.974
_diffrn_reflns_theta_max         30.090
_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             10296
_reflns_number_gt                6287
_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)+(0.0657P)²+0.6885P] 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       0.0105(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10296
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O1 O 0.56346(10) 0.26627(12) 0.29738(3) 0.0366(3) Uani 1 1 d . . . . .
N1 N 0.38407(12) 0.40195(14) 0.27877(3) 0.0317(3) Uani 1 1 d . . . . .
C1 C 0.49392(14) 0.37652(17) 0.30090(4) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.49616(14) 0.50102(18) 0.32439(4) 0.0303(3) Uani 1 1 d . . . . .
H2A H 0.557260 0.521936 0.343792 0.036 Uiso 1 1 calc R U . . .
N2 N 0.32401(12) 0.52860(15) 0.28626(4) 0.0331(3) Uani 1 1 d . . . . .
O2 O 0.71727(11) 0.42551(12) 0.40146(3) 0.0367(3) Uani 1 1 d . . . . .
O3 O 0.83486(11) 0.07635(12) 0.47483(3) 0.0382(3) Uani 1 1 d . . . . .
N3 N 0.39449(12) 0.58528(14) 0.31402(3) 0.0282(3) Uani 1 1 d . . . . .
C3 C 0.35843(14) 0.72986(17) 0.32751(4) 0.0280(3) Uani 1 1 d . . . . .
C4 C 0.25401(15) 0.73873(18) 0.34738(4) 0.0326(4) Uani 1 1 d . . . . .
N4 N 0.89326(12) 0.27227(14) 0.39910(3) 0.0305(3) Uani 1 1 d . . . . .
N5 N 0.92875(12) 0.14269(14) 0.38452(4) 0.0311(3) Uani 1 1 d . . . . .
C5 C 0.21710(16) 0.88105(19) 0.35747(5) 0.0372(4) Uani 1 1 d . . . . .
H5A H 0.145671 0.890698 0.370665 0.045 Uiso 1 1 calc R U . . .
N6 N 0.82586(12) 0.09842(13) 0.36530(3) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.28165(15) 1.01045(18) 0.34884(4) 0.0347(4) Uani 1 1 d . . . . .
N7 N 0.85004(12) 0.19408(13) 0.53158(3) 0.0279(3) Uani 1 1 d . . . . .
C7 C 0.38523(15) 0.99458(18) 0.32902(4) 0.0321(3) Uani 1 1 d . . . . .
H7A H 0.430343 1.081914 0.323310 0.039 Uiso 1 1 calc R U . . .
C8 C 0.42477(14) 0.85600(17) 0.31736(4) 0.0294(3) Uani 1 1 d . . . . .
N8 N 0.81393(12) 0.32016(14) 0.54760(3) 0.0293(3) Uani 1 1 d . . . . .
C9 C 0.18251(18) 0.6013(2) 0.35720(5) 0.0445(4) Uani 1 1 d . . . . .
H9A H 0.119431 0.629879 0.373488 0.067 Uiso 1 1 calc R U . . .
H9B H 0.240051 0.528280 0.369363 0.067 Uiso 1 1 calc R U . . .
H9C H 0.141522 0.556225 0.335153 0.067 Uiso 1 1 calc R U . . .
N9 N 0.74988(11) 0.39212(13) 0.52069(3) 0.0269(3) Uani 1 1 d . . . . .
C10 C 0.24053(18) 1.1635(2) 0.36023(6) 0.0470(5) Uani 1 1 d . . . . .
H10A H 0.259794 1.237835 0.342014 0.071 Uiso 1 1 calc R U . . .
H10B H 0.284517 1.189784 0.383643 0.071 Uiso 1 1 calc R U . . .
H10C H 0.150481 1.162552 0.362461 0.071 Uiso 1 1 calc R U . . .
C11 C 0.52934(16) 0.84583(19) 0.29309(5) 0.0368(4) Uani 1 1 d . . . . .
H11A H 0.594559 0.779380 0.304127 0.055 Uiso 1 1 calc R U . . .
H11B H 0.564174 0.946169 0.289822 0.055 Uiso 1 1 calc R U . . .
H11C H 0.497475 0.805318 0.269485 0.055 Uiso 1 1 calc R U . . .
C12 C 0.33076(18) 0.3033(2) 0.25024(5) 0.0470(5) Uani 1 1 d . . . . .
H12A H 0.380348 0.211058 0.249931 0.070 Uiso 1 1 calc R U . . .
H12B H 0.331147 0.354287 0.226802 0.070 Uiso 1 1 calc R U . . .
H12C H 0.244847 0.278137 0.254762 0.070 Uiso 1 1 calc R U . . .
C13 C 0.76854(15) 0.31016(16) 0.39013(4) 0.0290(3) Uani 1 1 d . . . . .
C14 C 0.72788(15) 0.19097(17) 0.36736(4) 0.0328(4) Uani 1 1 d . . . . .
H14A H 0.646596 0.177991 0.355623 0.039 Uiso 1 1 calc R U . . .
C15 C 0.82993(14) -0.04279(16) 0.34622(4) 0.0280(3) Uani 1 1 d . . . . .
C16 C 0.86842(15) -0.04360(18) 0.31124(4) 0.0342(4) Uani 1 1 d . . . . .
C17 C 0.87288(16) -0.18263(19) 0.29397(5) 0.0391(4) Uani 1 1 d . . . . .
H17A H 0.896018 -0.186571 0.269812 0.047 Uiso 1 1 calc R U . . .
C18 C 0.84450(15) -0.31488(18) 0.31109(5) 0.0366(4) Uani 1 1 d . . . . .
C19 C 0.80555(15) -0.30806(17) 0.34598(5) 0.0338(4) Uani 1 1 d . . . . .
H19A H 0.785765 -0.398575 0.357808 0.041 Uiso 1 1 calc R U . . .
C20 C 0.79494(14) -0.17162(16) 0.36390(4) 0.0293(3) Uani 1 1 d . . . . .
C21 C 0.9003(2) 0.0998(2) 0.29247(5) 0.0507(5) Uani 1 1 d . . . . .
H21A H 0.924489 0.076490 0.268182 0.076 Uiso 1 1 calc R U . . .
H21B H 0.969759 0.149822 0.306520 0.076 Uiso 1 1 calc R U . . .
H21C H 0.827538 0.166348 0.290500 0.076 Uiso 1 1 calc R U . . .
C22 C 0.8530(2) -0.4649(2) 0.29227(6) 0.0549(5) Uani 1 1 d . . . . .
H22A H 0.860383 -0.448593 0.266385 0.082 Uiso 1 1 calc R U . . .
H22B H 0.777658 -0.523715 0.295408 0.082 Uiso 1 1 calc R U . . .
H22C H 0.926291 -0.519677 0.302830 0.082 Uiso 1 1 calc R U . . .
C23 C 0.74089(17) -0.16540(19) 0.40014(5) 0.0391(4) Uani 1 1 d . . . . .
H23A H 0.744936 -0.265429 0.411238 0.059 Uiso 1 1 calc R U . . .
H23B H 0.653797 -0.132492 0.396700 0.059 Uiso 1 1 calc R U . . .
H23C H 0.788846 -0.094240 0.415995 0.059 Uiso 1 1 calc R U . . .
C24 C 0.98256(17) 0.3558(2) 0.42295(5) 0.0470(5) Uani 1 1 d . . . . .
H24A H 0.956908 0.461348 0.423653 0.070 Uiso 1 1 calc R U . . .
H24B H 1.065240 0.349144 0.413876 0.070 Uiso 1 1 calc R U . . .
H24C H 0.985761 0.313261 0.447416 0.070 Uiso 1 1 calc R U . . .
C25 C 0.81076(14) 0.18361(16) 0.49465(4) 0.0289(3) Uani 1 1 d . . . . .
C26 C 0.74452(14) 0.31907(16) 0.48870(4) 0.0297(3) Uani 1 1 d . . . . .
H26A H 0.703788 0.352615 0.466383 0.036 Uiso 1 1 calc R U . . .
C27 C 0.69408(14) 0.53511(16) 0.52839(4) 0.0274(3) Uani 1 1 d . . . . .
C28 C 0.73923(15) 0.66329(17) 0.51249(4) 0.0306(3) Uani 1 1 d . . . . .
C29 C 0.68431(16) 0.79999(17) 0.52029(5) 0.0357(4) Uani 1 1 d . . . . .
H29A H 0.712157 0.889276 0.509476 0.043 Uiso 1 1 calc R U . . .
C30 C 0.58921(16) 0.80896(17) 0.54365(5) 0.0359(4) Uani 1 1 d . . . . .
C31 C 0.54768(15) 0.67698(18) 0.55883(5) 0.0336(4) Uani 1 1 d . . . . .
H31A H 0.483952 0.682587 0.574996 0.040 Uiso 1 1 calc R U . . .
C32 C 0.59667(14) 0.53717(17) 0.55106(4) 0.0293(3) Uani 1 1 d . . . . .
C33 C 0.84381(16) 0.65841(19) 0.48784(5) 0.0391(4) Uani 1 1 d . . . . .
H33A H 0.873749 0.760660 0.483977 0.059 Uiso 1 1 calc R U . . .
H33B H 0.813219 0.614237 0.464519 0.059 Uiso 1 1 calc R U . . .
H33C H 0.912330 0.597151 0.499036 0.059 Uiso 1 1 calc R U . . .
C34 C 0.5324(2) 0.9584(2) 0.55247(6) 0.0521(5) Uani 1 1 d . . . . .
H34A H 0.560495 1.035738 0.536192 0.078 Uiso 1 1 calc R U . . .
H34B H 0.558699 0.985449 0.577620 0.078 Uiso 1 1 calc R U . . .
H34C H 0.441334 0.950827 0.549331 0.078 Uiso 1 1 calc R U . . .
C35 C 0.54220(16) 0.39578(18) 0.56549(5) 0.0378(4) Uani 1 1 d . . . . .
H35A H 0.470210 0.421350 0.578777 0.057 Uiso 1 1 calc R U . . .
H35B H 0.605336 0.345079 0.581817 0.057 Uiso 1 1 calc R U . . .
H35C H 0.515606 0.328887 0.545272 0.057 Uiso 1 1 calc R U . . .
C36 C 0.92248(16) 0.08257(18) 0.55295(5) 0.0359(4) Uani 1 1 d . . . . .
H36A H 0.976143 0.028009 0.537361 0.054 Uiso 1 1 calc R U . . .
H36B H 0.865959 0.011738 0.563468 0.054 Uiso 1 1 calc R U . . .
H36C H 0.974181 0.132791 0.572416 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
O1 C1 1.2477(19) . ?
N1 N2 1.3403(18) . ?
N1 C1 1.3979(19) . ?
N1 C12 1.453(2) . ?
C1 C2 1.408(2) . ?
C2 N3 1.355(2) . ?
C2 H2A 0.9500 . ?
N2 N3 1.3240(18) . ?
O2 C13 1.2547(18) . ?
O3 C25 1.2452(18) . ?
N3 C3 1.445(2) . ?
C3 C4 1.398(2) . ?
C3 C8 1.399(2) . ?
C4 C5 1.388(2) . ?
C4 C9 1.507(2) . ?
N4 N5 1.3428(18) . ?
N4 C13 1.396(2) . ?
N4 C24 1.453(2) . ?
N5 N6 1.3240(18) . ?
C5 C6 1.396(2) . ?
C5 H5A 0.9500 . ?
N6 C14 1.346(2) . ?
N6 C15 1.4443(19) . ?
C6 C7 1.394(2) . ?
C6 C10 1.504(2) . ?
N7 N8 1.3424(17) . ?
N7 C25 1.400(2) . ?
N7 C36 1.4535(19) . ?
C7 C8 1.386(2) . ?
C7 H7A 0.9500 . ?
C8 C11 1.503(2) . ?
N8 N9 1.3271(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N9 C26 1.348(2) . ?
N9 C27 1.4461(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.402(2) . ?
C14 H14A 0.9500 . ?
C15 C20 1.389(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.396(2) . ?
C16 C21 1.507(2) . ?
C17 C18 1.384(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.394(3) . ?
C18 C22 1.513(2) . ?
C19 C20 1.393(2) . ?
C19 H19A 0.9500 . ?
C20 C23 1.509(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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 C26 1.408(2) . ?
C26 H26A 0.9500 . ?
C27 C28 1.390(2) . ?
C27 C32 1.399(2) . ?
C28 C29 1.394(2) . ?
C28 C33 1.510(2) . ?
C29 C30 1.398(3) . ?
C29 H29A 0.9500 . ?
C30 C31 1.393(2) . ?
C30 C34 1.511(2) . ?
C31 C32 1.391(2) . ?
C31 H31A 0.9500 . ?
C32 C35 1.506(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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 C1 114.43(12) . . ?
N2 N1 C12 119.41(13) . . ?
C1 N1 C12 126.13(14) . . ?
O1 C1 N1 123.43(14) . . ?
O1 C1 C2 134.82(14) . . ?
N1 C1 C2 101.75(13) . . ?
N3 C2 C1 106.86(13) . . ?
N3 C2 H2A 126.6 . . ?
C1 C2 H2A 126.6 . . ?
N3 N2 N1 103.10(12) . . ?
N2 N3 C2 113.84(13) . . ?
N2 N3 C3 117.03(12) . . ?
C2 N3 C3 129.00(13) . . ?
C4 C3 C8 123.26(14) . . ?
C4 C3 N3 118.97(13) . . ?
C8 C3 N3 117.56(13) . . ?
C5 C4 C3 117.07(14) . . ?
C5 C4 C9 120.77(15) . . ?
C3 C4 C9 122.16(15) . . ?
N5 N4 C13 114.38(12) . . ?
N5 N4 C24 119.19(13) . . ?
C13 N4 C24 126.40(14) . . ?
N6 N5 N4 102.59(12) . . ?
C4 C5 C6 122.08(15) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
N5 N6 C14 114.25(13) . . ?
N5 N6 C15 117.57(12) . . ?
C14 N6 C15 128.13(13) . . ?
C7 C6 C5 118.26(15) . . ?
C7 C6 C10 120.52(15) . . ?
C5 C6 C10 121.22(15) . . ?
N8 N7 C25 114.39(12) . . ?
N8 N7 C36 119.49(13) . . ?
C25 N7 C36 126.12(13) . . ?
C8 C7 C6 122.38(15) . . ?
C8 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
C7 C8 C3 116.90(14) . . ?
C7 C8 C11 120.41(14) . . ?
C3 C8 C11 122.58(14) . . ?
N9 N8 N7 102.87(12) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N8 N9 C26 114.06(12) . . ?
N8 N9 C27 118.30(12) . . ?
C26 N9 C27 127.64(13) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N4 124.03(14) . . ?
O2 C13 C14 134.17(15) . . ?
N4 C13 C14 101.80(13) . . ?
N6 C14 C13 106.96(14) . . ?
N6 C14 H14A 126.5 . . ?
C13 C14 H14A 126.5 . . ?
C20 C15 C16 123.27(14) . . ?
C20 C15 N6 117.82(13) . . ?
C16 C15 N6 118.91(13) . . ?
C15 C16 C17 117.09(14) . . ?
C15 C16 C21 121.48(14) . . ?
C17 C16 C21 121.40(15) . . ?
C18 C17 C16 121.75(16) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C19 118.95(15) . . ?
C17 C18 C22 121.00(16) . . ?
C19 C18 C22 120.04(16) . . ?
C20 C19 C18 121.56(15) . . ?
C20 C19 H19A 119.2 . . ?
C18 C19 H19A 119.2 . . ?
C15 C20 C19 117.26(14) . . ?
C15 C20 C23 122.03(14) . . ?
C19 C20 C23 120.64(14) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 N7 124.51(14) . . ?
O3 C25 C26 133.82(15) . . ?
N7 C25 C26 101.67(12) . . ?
N9 C26 C25 107.01(14) . . ?
N9 C26 H26A 126.5 . . ?
C25 C26 H26A 126.5 . . ?
C28 C27 C32 123.43(13) . . ?
C28 C27 N9 118.17(13) . . ?
C32 C27 N9 118.40(13) . . ?
C27 C28 C29 117.28(15) . . ?
C27 C28 C33 122.57(14) . . ?
C29 C28 C33 120.14(14) . . ?
C28 C29 C30 121.62(15) . . ?
C28 C29 H29A 119.2 . . ?
C30 C29 H29A 119.2 . . ?
C31 C30 C29 118.65(14) . . ?
C31 C30 C34 120.33(16) . . ?
C29 C30 C34 121.02(16) . . ?
C32 C31 C30 122.01(15) . . ?
C32 C31 H31A 119.0 . . ?
C30 C31 H31A 119.0 . . ?
C31 C32 C27 116.94(14) . . ?
C31 C32 C35 120.51(14) . . ?
C27 C32 C35 122.49(13) . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34A 109.5 . . ?
C30 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C30 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N7 C36 H36A 109.5 . . ?
N7 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N7 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
N2 N1 C1 O1 -178.35(14) . . . . ?
C12 N1 C1 O1 3.5(3) . . . . ?
N2 N1 C1 C2 1.41(17) . . . . ?
C12 N1 C1 C2 -176.72(16) . . . . ?
O1 C1 C2 N3 178.52(17) . . . . ?
N1 C1 C2 N3 -1.20(16) . . . . ?
C1 N1 N2 N3 -1.01(17) . . . . ?
C12 N1 N2 N3 177.26(15) . . . . ?
N1 N2 N3 C2 0.14(17) . . . . ?
N1 N2 N3 C3 176.39(12) . . . . ?
C1 C2 N3 N2 0.72(18) . . . . ?
C1 C2 N3 C3 -174.97(14) . . . . ?
N2 N3 C3 C4 73.40(18) . . . . ?
C2 N3 C3 C4 -111.02(18) . . . . ?
N2 N3 C3 C8 -101.55(16) . . . . ?
C2 N3 C3 C8 74.0(2) . . . . ?
C8 C3 C4 C5 -0.6(2) . . . . ?
N3 C3 C4 C5 -175.28(14) . . . . ?
C8 C3 C4 C9 178.55(15) . . . . ?
N3 C3 C4 C9 3.9(2) . . . . ?
C13 N4 N5 N6 1.27(16) . . . . ?
C24 N4 N5 N6 179.24(14) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C9 C4 C5 C6 179.83(16) . . . . ?
N4 N5 N6 C14 -0.92(16) . . . . ?
N4 N5 N6 C15 -178.51(12) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C4 C5 C6 C10 -179.62(17) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C10 C6 C7 C8 -178.67(16) . . . . ?
C6 C7 C8 C3 -2.3(2) . . . . ?
C6 C7 C8 C11 174.14(15) . . . . ?
C4 C3 C8 C7 2.2(2) . . . . ?
N3 C3 C8 C7 176.93(13) . . . . ?
C4 C3 C8 C11 -174.14(15) . . . . ?
N3 C3 C8 C11 0.6(2) . . . . ?
C25 N7 N8 N9 0.25(16) . . . . ?
C36 N7 N8 N9 -179.04(13) . . . . ?
N7 N8 N9 C26 -0.46(16) . . . . ?
N7 N8 N9 C27 179.07(12) . . . . ?
N5 N4 C13 O2 178.94(14) . . . . ?
C24 N4 C13 O2 1.1(2) . . . . ?
N5 N4 C13 C14 -1.11(16) . . . . ?
C24 N4 C13 C14 -178.91(16) . . . . ?
N5 N6 C14 C13 0.28(18) . . . . ?
C15 N6 C14 C13 177.56(14) . . . . ?
O2 C13 C14 N6 -179.58(16) . . . . ?
N4 C13 C14 N6 0.48(16) . . . . ?
N5 N6 C15 C20 91.77(17) . . . . ?
C14 N6 C15 C20 -85.4(2) . . . . ?
N5 N6 C15 C16 -88.22(17) . . . . ?
C14 N6 C15 C16 94.6(2) . . . . ?
C20 C15 C16 C17 -1.0(2) . . . . ?
N6 C15 C16 C17 179.03(14) . . . . ?
C20 C15 C16 C21 177.35(16) . . . . ?
N6 C15 C16 C21 -2.7(2) . . . . ?
C15 C16 C17 C18 -2.1(3) . . . . ?
C21 C16 C17 C18 179.57(17) . . . . ?
C16 C17 C18 C19 2.7(3) . . . . ?
C16 C17 C18 C22 -178.46(16) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C22 C18 C19 C20 -179.04(16) . . . . ?
C16 C15 C20 C19 3.3(2) . . . . ?
N6 C15 C20 C19 -176.69(13) . . . . ?
C16 C15 C20 C23 -173.43(16) . . . . ?
N6 C15 C20 C23 6.6(2) . . . . ?
C18 C19 C20 C15 -2.7(2) . . . . ?
C18 C19 C20 C23 174.08(16) . . . . ?
N8 N7 C25 O3 179.62(14) . . . . ?
C36 N7 C25 O3 -1.1(2) . . . . ?
N8 N7 C25 C26 0.02(16) . . . . ?
C36 N7 C25 C26 179.26(14) . . . . ?
N8 N9 C26 C25 0.50(18) . . . . ?
C27 N9 C26 C25 -178.98(14) . . . . ?
O3 C25 C26 N9 -179.83(17) . . . . ?
N7 C25 C26 N9 -0.29(16) . . . . ?
N8 N9 C27 C28 113.72(16) . . . . ?
C26 N9 C27 C28 -66.8(2) . . . . ?
N8 N9 C27 C32 -67.01(18) . . . . ?
C26 N9 C27 C32 112.45(17) . . . . ?
C32 C27 C28 C29 0.8(2) . . . . ?
N9 C27 C28 C29 -179.93(13) . . . . ?
C32 C27 C28 C33 -179.48(15) . . . . ?
N9 C27 C28 C33 -0.2(2) . . . . ?
C27 C28 C29 C30 1.1(2) . . . . ?
C33 C28 C29 C30 -178.54(16) . . . . ?
C28 C29 C30 C31 -1.1(2) . . . . ?
C28 C29 C30 C34 178.68(16) . . . . ?
C29 C30 C31 C32 -0.9(2) . . . . ?
C34 C30 C31 C32 179.29(16) . . . . ?
C30 C31 C32 C27 2.7(2) . . . . ?
C30 C31 C32 C35 -174.86(15) . . . . ?
C28 C27 C32 C31 -2.7(2) . . . . ?
N9 C27 C32 C31 178.04(13) . . . . ?
C28 C27 C32 C35 174.82(15) . . . . ?
N9 C27 C32 C35 -4.4(2) . . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.305
_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_wl472
_database_code_depnum_ccdc_archive 'CCDC 2104500'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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 H26 B F4 N3'
_chemical_formula_weight         455.30

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'
B B 0.0013 0.0007 '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                   11.045(6)
_cell_length_b                   13.979(6)
_cell_length_c                   14.811(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.520(13)
_cell_angle_gamma                90
_cell_volume                     2282.4(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    32545
_cell_measurement_theta_min      3.224
_cell_measurement_theta_max      27.433

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6661
_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            32545
_diffrn_reflns_av_unetI/netI     0.1072
_diffrn_reflns_av_R_equivalents  0.1125
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.224
_diffrn_reflns_theta_max         27.433
_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             5173
_reflns_number_gt                2849
_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)+(0.0689P)²+1.6101P] 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         5173
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 1.0466(5) 0.1106(3) 0.2606(3) 0.0667(10) Uiso 0.5 1 d . . P A 1
F1A F 1.0641(5) 0.0723(3) 0.2430(3) 0.0667(10) Uiso 0.5 1 d . . P A 2
N1 N 0.7285(2) 0.31661(15) 0.29897(14) 0.0255(5) Uani 1 1 d . . . . .
C1 C 1.0836(3) 0.4456(2) 0.35780(19) 0.0321(7) Uani 1 1 d . . . . .
H1 H 1.138985 0.394559 0.350847 0.038 Uiso 1 1 calc R U . . .
B1 B 0.9305(4) 0.0863(2) 0.2410(2) 0.0356(8) Uani 1 1 d . . . . .
F2 F 0.8936(3) 0.16744(18) 0.1993(2) 0.1149(12) Uani 1 1 d . . . . .
N2 N 0.6132(2) 0.29110(16) 0.30271(14) 0.0276(5) Uani 1 1 d . . . . .
C2 C 1.1221(3) 0.5394(2) 0.3466(2) 0.0392(8) Uani 1 1 d . . . . .
H2 H 1.203308 0.552253 0.332538 0.047 Uiso 1 1 calc R U . . .
F3 F 0.8859(2) 0.07617(18) 0.32524(14) 0.0793(8) Uani 1 1 d . . . . .
N3 N 0.6072(2) 0.25644(15) 0.38583(14) 0.0237(5) Uani 1 1 d . . . . .
C3 C 1.0406(3) 0.6141(2) 0.3561(2) 0.0382(8) Uani 1 1 d . . . . .
H3 H 1.065666 0.678364 0.347811 0.046 Uiso 1 1 calc R U . . .
F4 F 0.9003(2) 0.00949(15) 0.18915(15) 0.0736(7) Uani 1 1 d . . . . .
C4 C 0.9238(3) 0.5947(2) 0.37759(19) 0.0371(8) Uani 1 1 d . . . . .
H4 H 0.868411 0.645865 0.384101 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8858(3) 0.50102(19) 0.38990(19) 0.0325(7) Uani 1 1 d . . . . .
H5 H 0.805244 0.488664 0.405787 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9654(3) 0.42539(19) 0.37901(17) 0.0269(6) Uani 1 1 d . . . . .
C7 C 0.9287(3) 0.32132(19) 0.39158(19) 0.0287(7) Uani 1 1 d . . . . .
H7A H 0.972778 0.281548 0.349057 0.034 Uiso 1 1 calc R U . . .
H7AB H 0.956087 0.301393 0.453661 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7962(3) 0.29993(18) 0.37748(17) 0.0237(6) Uani 1 1 d . . . . .
C9 C 0.7169(3) 0.25968(18) 0.43464(17) 0.0234(6) Uani 1 1 d . . . . .
C10 C 0.7404(2) 0.22081(18) 0.52718(17) 0.0233(6) Uani 1 1 d . . . . .
C11 C 0.8333(3) 0.15336(19) 0.54143(18) 0.0258(6) Uani 1 1 d . . . . .
H11 H 0.875700 0.130661 0.491823 0.031 Uiso 1 1 calc R U . . .
C12 C 0.8632(3) 0.11982(19) 0.62768(19) 0.0303(7) Uani 1 1 d . . . . .
H12 H 0.927271 0.074984 0.637388 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8004(3) 0.1511(2) 0.69980(19) 0.0347(7) Uani 1 1 d . . . . .
H13 H 0.821099 0.127274 0.758803 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7072(3) 0.2172(2) 0.68673(19) 0.0375(8) Uani 1 1 d . . . . .
H14 H 0.664592 0.238777 0.736692 0.045 Uiso 1 1 calc R U . . .
C15 C 0.6762(3) 0.2519(2) 0.60005(19) 0.0322(7) Uani 1 1 d . . . . .
H15 H 0.611722 0.296471 0.590642 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4913(2) 0.22072(18) 0.41288(16) 0.0231(6) Uani 1 1 d . . . . .
C17 C 0.4082(3) 0.28578(19) 0.44488(17) 0.0262(6) Uani 1 1 d . . . . .
C18 C 0.2962(3) 0.24873(19) 0.46776(18) 0.0276(6) Uani 1 1 d . . . . .
H18 H 0.237501 0.291016 0.489844 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2683(3) 0.15217(19) 0.45918(17) 0.0260(6) Uani 1 1 d . . . . .
C20 C 0.3554(3) 0.0906(2) 0.42696(18) 0.0275(6) Uani 1 1 d . . . . .
H20 H 0.336592 0.024545 0.420830 0.033 Uiso 1 1 calc R U . . .
C21 C 0.4682(3) 0.12231(18) 0.40355(17) 0.0244(6) Uani 1 1 d . . . . .
C22 C 0.4350(3) 0.39151(19) 0.4563(2) 0.0329(7) Uani 1 1 d . . . . .
H22A H 0.479326 0.414194 0.405067 0.049 Uiso 1 1 calc R U . . .
H22B H 0.484404 0.401839 0.512654 0.049 Uiso 1 1 calc R U . . .
H22C H 0.358641 0.426898 0.458383 0.049 Uiso 1 1 calc R U . . .
C23 C 0.1460(3) 0.1154(2) 0.4833(2) 0.0365(7) Uani 1 1 d . . . . .
H23A H 0.097151 0.099562 0.427899 0.055 Uiso 1 1 calc R U . . .
H23B H 0.104581 0.164730 0.516904 0.055 Uiso 1 1 calc R U . . .
H23C H 0.156956 0.057974 0.520932 0.055 Uiso 1 1 calc R U . . .
C24 C 0.5624(3) 0.05455(19) 0.37022(19) 0.0319(7) Uani 1 1 d . . . . .
H24A H 0.525697 -0.008469 0.358878 0.048 Uiso 1 1 calc R U . . .
H24B H 0.629770 0.048779 0.416132 0.048 Uiso 1 1 calc R U . . .
H24C H 0.592802 0.079442 0.314037 0.048 Uiso 1 1 calc R U . . .
C25 C 0.7671(3) 0.3586(2) 0.21428(18) 0.0335(7) Uani 1 1 d . . . . .
H25A H 0.710265 0.339571 0.164056 0.050 Uiso 1 1 calc R U . . .
H25B H 0.848606 0.335653 0.202927 0.050 Uiso 1 1 calc R U . . .
H25C H 0.768084 0.428468 0.219458 0.050 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 B1 1.340(6) . ?
F1A B1 1.487(6) . ?
N1 N2 1.327(3) . ?
N1 C8 1.364(3) . ?
N1 C25 1.471(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.391(4) . ?
B1 F2 1.343(4) . ?
B1 F4 1.350(4) . ?
B1 F3 1.376(4) . ?
N2 N3 1.328(3) . ?
C2 C3 1.392(5) . ?
N3 C9 1.373(3) . ?
N3 C16 1.453(3) . ?
C3 C4 1.375(4) . ?
C4 C5 1.391(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.525(4) . ?
C7 C8 1.496(4) . ?
C8 C9 1.376(4) . ?
C9 C10 1.482(4) . ?
C10 C15 1.397(4) . ?
C10 C11 1.400(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.395(4) . ?
C16 C17 1.396(4) . ?
C16 C21 1.405(4) . ?
C17 C18 1.402(4) . ?
C17 C22 1.515(4) . ?
C18 C19 1.389(4) . ?
C19 C20 1.396(4) . ?
C19 C23 1.508(4) . ?
C20 C21 1.386(4) . ?
C21 C24 1.512(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 113.3(2) . . ?
N2 N1 C25 118.2(2) . . ?
C8 N1 C25 128.5(2) . . ?
C2 C1 C6 121.1(3) . . ?
F1 B1 F2 98.3(3) . . ?
F1 B1 F4 121.6(4) . . ?
F2 B1 F4 110.6(3) . . ?
F1 B1 F3 102.8(3) . . ?
F2 B1 F3 112.8(3) . . ?
F4 B1 F3 110.1(3) . . ?
F2 B1 F1A 113.1(4) . . ?
F4 B1 F1A 96.7(3) . . ?
F3 B1 F1A 112.3(3) . . ?
N1 N2 N3 103.8(2) . . ?
C1 C2 C3 119.4(3) . . ?
N2 N3 C9 112.5(2) . . ?
N2 N3 C16 118.4(2) . . ?
C9 N3 C16 129.1(2) . . ?
C4 C3 C2 119.8(3) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C5 C4 120.2(3) . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 122.5(3) . . ?
C1 C6 C7 118.8(3) . . ?
C8 C7 C6 116.0(2) . . ?
N1 C8 C9 104.9(2) . . ?
N1 C8 C7 124.5(2) . . ?
C9 C8 C7 130.6(2) . . ?
N3 C9 C8 105.3(2) . . ?
N3 C9 C10 125.0(2) . . ?
C8 C9 C10 129.6(3) . . ?
C15 C10 C11 119.7(2) . . ?
C15 C10 C9 122.1(2) . . ?
C11 C10 C9 118.1(2) . . ?
C12 C11 C10 120.0(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C14 120.4(3) . . ?
C13 C14 C15 119.9(3) . . ?
C14 C15 C10 119.7(3) . . ?
C17 C16 C21 123.5(3) . . ?
C17 C16 N3 118.6(2) . . ?
C21 C16 N3 117.9(2) . . ?
C16 C17 C18 116.7(2) . . ?
C16 C17 C22 123.1(3) . . ?
C18 C17 C22 120.2(3) . . ?
C19 C18 C17 122.1(3) . . ?
C18 C19 C20 118.5(3) . . ?
C18 C19 C23 120.4(3) . . ?
C20 C19 C23 121.1(3) . . ?
C21 C20 C19 122.5(3) . . ?
C20 C21 C16 116.7(2) . . ?
C20 C21 C24 121.9(2) . . ?
C16 C21 C24 121.4(3) . . ?

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 -0.5(3) . . . . ?
C25 N1 N2 N3 179.9(2) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
N1 N2 N3 C9 0.0(3) . . . . ?
N1 N2 N3 C16 -179.6(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 -179.3(3) . . . . ?
C5 C6 C7 C8 25.0(4) . . . . ?
C1 C6 C7 C8 -156.5(2) . . . . ?
N2 N1 C8 C9 0.7(3) . . . . ?
C25 N1 C8 C9 -179.7(2) . . . . ?
N2 N1 C8 C7 179.6(2) . . . . ?
C25 N1 C8 C7 -0.9(4) . . . . ?
C6 C7 C8 N1 59.2(3) . . . . ?
C6 C7 C8 C9 -122.2(3) . . . . ?
N2 N3 C9 C8 0.4(3) . . . . ?
C16 N3 C9 C8 180.0(2) . . . . ?
N2 N3 C9 C10 -176.0(2) . . . . ?
C16 N3 C9 C10 3.5(4) . . . . ?
N1 C8 C9 N3 -0.6(3) . . . . ?
C7 C8 C9 N3 -179.4(3) . . . . ?
N1 C8 C9 C10 175.6(2) . . . . ?
C7 C8 C9 C10 -3.2(5) . . . . ?
N3 C9 C10 C15 -58.6(4) . . . . ?
C8 C9 C10 C15 125.9(3) . . . . ?
N3 C9 C10 C11 123.8(3) . . . . ?
C8 C9 C10 C11 -51.8(4) . . . . ?
C15 C10 C11 C12 -1.7(4) . . . . ?
C9 C10 C11 C12 176.0(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C10 -0.9(5) . . . . ?
C11 C10 C15 C14 1.6(4) . . . . ?
C9 C10 C15 C14 -176.0(3) . . . . ?
N2 N3 C16 C17 -84.1(3) . . . . ?
C9 N3 C16 C17 96.4(3) . . . . ?
N2 N3 C16 C21 94.7(3) . . . . ?
C9 N3 C16 C21 -84.9(3) . . . . ?
C21 C16 C17 C18 -0.5(4) . . . . ?
N3 C16 C17 C18 178.2(2) . . . . ?
C21 C16 C17 C22 178.9(3) . . . . ?
N3 C16 C17 C22 -2.5(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C22 C17 C18 C19 -179.4(2) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C17 C18 C19 C23 -179.2(2) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C23 C19 C20 C21 179.5(2) . . . . ?
C19 C20 C21 C16 -0.6(4) . . . . ?
C19 C20 C21 C24 179.0(2) . . . . ?
C17 C16 C21 C20 0.8(4) . . . . ?
N3 C16 C21 C20 -177.9(2) . . . . ?
C17 C16 C21 C24 -178.8(2) . . . . ?
N3 C16 C21 C24 2.5(4) . . . . ?

_refine_diff_density_max         0.557
_refine_diff_density_min         -0.503
_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_wl529
_database_code_depnum_ccdc_archive 'CCDC 2104504'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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            'C23 H21 N3 O'
_chemical_formula_weight         355.43

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           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                   21.598(6)
_cell_length_b                   10.343(3)
_cell_length_c                   18.170(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.301(7)
_cell_angle_gamma                90
_cell_volume                     3830.7(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    55884
_cell_measurement_theta_min      2.659
_cell_measurement_theta_max      27.581

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_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  0.7033
_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            55884
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.659
_diffrn_reflns_theta_max         27.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4414
_reflns_number_gt                3377
_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)+(0.0518P)²+2.5080P] 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       0.0058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4414
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.40080(4) 0.47825(9) 0.33104(5) 0.0311(2) Uani 1 1 d . . . . .
C1 C 0.38306(6) 0.51525(12) 0.38576(7) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.33008(5) 0.46452(10) 0.40515(6) 0.0270(2) Uani 1 1 d . . . . .
N2 N 0.32187(5) 0.52011(11) 0.46864(6) 0.0289(3) Uani 1 1 d . . . . .
C2 C 0.40778(6) 0.61117(12) 0.44386(7) 0.0259(3) Uani 1 1 d . . . . .
N3 N 0.36965(5) 0.60672(10) 0.48980(6) 0.0265(2) Uani 1 1 d . . . . .
C3 C 0.46289(6) 0.69927(12) 0.45319(8) 0.0280(3) Uani 1 1 d . . . . .
C4 C 0.46996(7) 0.75507(15) 0.38662(9) 0.0402(4) Uani 1 1 d . . . . .
H4 H 0.438904 0.737042 0.336810 0.048 Uiso 1 1 calc R U . . .
C5 C 0.52221(9) 0.83671(18) 0.39309(10) 0.0545(5) Uani 1 1 d . . . . .
H5 H 0.526867 0.874987 0.347676 0.065 Uiso 1 1 calc R U . . .
C6 C 0.56758(9) 0.86274(18) 0.46522(11) 0.0557(5) Uani 1 1 d . . . . .
H6 H 0.603089 0.919711 0.469434 0.067 Uiso 1 1 calc R U . . .
C7 C 0.56154(8) 0.80646(18) 0.53104(10) 0.0486(4) Uani 1 1 d . . . . .
H7 H 0.593193 0.823656 0.580584 0.058 Uiso 1 1 calc R U . . .
C8 C 0.50938(7) 0.72478(15) 0.52520(8) 0.0367(3) Uani 1 1 d . . . . .
H8 H 0.505409 0.685951 0.570813 0.044 Uiso 1 1 calc R U . . .
C9 C 0.37232(6) 0.68918(13) 0.55514(7) 0.0273(3) Uani 1 1 d . . . . .
C10 C 0.40347(6) 0.64361(14) 0.63046(8) 0.0311(3) Uani 1 1 d . . . . .
C19 C 0.25066(8) 0.30346(16) 0.40883(9) 0.0472(4) Uani 1 1 d . . . . .
H19 H 0.255538 0.329919 0.460512 0.057 Uiso 1 1 calc R U . . .
C20 C 0.20751(9) 0.20527(18) 0.37380(10) 0.0556(5) Uani 1 1 d . . . . .
H20 H 0.183087 0.163795 0.401965 0.067 Uiso 1 1 calc R U . . .
C21 C 0.19948(8) 0.16686(15) 0.29877(9) 0.0434(4) Uani 1 1 d . . . . .
H21 H 0.169609 0.099681 0.274857 0.052 Uiso 1 1 calc R U . . .
C22 C 0.23537(8) 0.22725(17) 0.25902(9) 0.0473(4) Uani 1 1 d . . . . .
H22 H 0.230188 0.200953 0.207225 0.057 Uiso 1 1 calc R U . . .
C23 C 0.27908(8) 0.32590(15) 0.29281(8) 0.0409(4) Uani 1 1 d . . . . .
H23 H 0.303418 0.367363 0.264547 0.049 Uiso 1 1 calc R U . . .
C18 C 0.28647(6) 0.36254(13) 0.36816(7) 0.0290(3) Uani 1 1 d . . . . .
C17 C 0.30833(7) 0.85484(14) 0.45671(8) 0.0362(3) Uani 1 1 d . . . . .
H17A H 0.340662 0.869433 0.430377 0.054 Uiso 1 1 calc R U . . .
H17B H 0.284828 0.935575 0.457599 0.054 Uiso 1 1 calc R U . . .
H17C H 0.277027 0.788507 0.428594 0.054 Uiso 1 1 calc R U . . .
C16 C 0.38386(10) 0.94074(19) 0.74553(10) 0.0576(5) Uani 1 1 d . . . . .
H16A H 0.372823 1.028858 0.725706 0.086 Uiso 1 1 calc R U . . .
H16B H 0.428758 0.939066 0.782429 0.086 Uiso 1 1 calc R U . . .
H16C H 0.353312 0.912800 0.772022 0.086 Uiso 1 1 calc R U . . .
C15 C 0.43518(7) 0.51298(14) 0.64658(8) 0.0368(3) Uani 1 1 d . . . . .
H15A H 0.414117 0.454997 0.602794 0.055 Uiso 1 1 calc R U . . .
H15B H 0.430245 0.477577 0.694364 0.055 Uiso 1 1 calc R U . . .
H15C H 0.481918 0.520974 0.653130 0.055 Uiso 1 1 calc R U . . .
C14 C 0.34275(6) 0.81042(13) 0.53881(8) 0.0297(3) Uani 1 1 d . . . . .
C13 C 0.34668(7) 0.88927(14) 0.60223(8) 0.0349(3) Uani 1 1 d . . . . .
H13 H 0.326754 0.972277 0.593077 0.042 Uiso 1 1 calc R U . . .
C12 C 0.37874(7) 0.85046(15) 0.67830(8) 0.0388(3) Uani 1 1 d . . . . .
C11 C 0.40601(7) 0.72739(15) 0.69145(8) 0.0372(3) Uani 1 1 d . . . . .
H11 H 0.427021 0.699531 0.743593 0.045 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 C1 1.2384(15) . ?
C1 N1 1.4055(16) . ?
C1 C2 1.4182(18) . ?
N1 N2 1.3521(15) . ?
N1 C18 1.4258(16) . ?
N2 N3 1.3239(15) . ?
C2 N3 1.3532(16) . ?
C2 C3 1.4637(17) . ?
N3 C9 1.4474(16) . ?
C3 C8 1.3861(19) . ?
C3 C4 1.3934(19) . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.3926(18) . ?
C9 C14 1.3939(19) . ?
C10 C11 1.393(2) . ?
C10 C15 1.499(2) . ?
C19 C18 1.377(2) . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(2) . ?
C22 H22 0.9500 . ?
C23 C18 1.3781(19) . ?
C23 H23 0.9500 . ?
C17 C14 1.5021(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 C12 1.512(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 C13 1.3912(19) . ?
C13 C12 1.385(2) . ?
C13 H13 0.9500 . ?
C12 C11 1.390(2) . ?
C11 H11 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
O1 C1 N1 125.41(12) . . ?
O1 C1 C2 132.35(12) . . ?
N1 C1 C2 102.23(10) . . ?
N2 N1 C1 113.73(10) . . ?
N2 N1 C18 117.66(10) . . ?
C1 N1 C18 128.59(11) . . ?
N3 N2 N1 103.06(9) . . ?
N3 C2 C1 106.22(10) . . ?
N3 C2 C3 125.95(11) . . ?
C1 C2 C3 127.82(11) . . ?
N2 N3 C2 114.75(10) . . ?
N2 N3 C9 116.92(10) . . ?
C2 N3 C9 128.20(10) . . ?
C8 C3 C4 119.18(12) . . ?
C8 C3 C2 122.37(12) . . ?
C4 C3 C2 118.40(12) . . ?
C5 C4 C3 119.98(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.23(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.16(15) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.05(15) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 120.39(13) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C10 C9 C14 123.51(12) . . ?
C10 C9 N3 118.82(12) . . ?
C14 C9 N3 117.66(11) . . ?
C9 C10 C11 116.77(13) . . ?
C9 C10 C15 122.55(12) . . ?
C11 C10 C15 120.64(12) . . ?
C18 C19 C20 119.45(14) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.89(15) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 118.85(14) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 121.45(14) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C18 C23 C22 118.70(14) . . ?
C18 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C19 C18 C23 120.66(13) . . ?
C19 C18 N1 118.44(12) . . ?
C23 C18 N1 120.89(12) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 C9 116.93(12) . . ?
C13 C14 C17 121.19(13) . . ?
C9 C14 C17 121.87(12) . . ?
C12 C13 C14 122.01(14) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C13 C12 C11 118.73(13) . . ?
C13 C12 C16 120.40(15) . . ?
C11 C12 C16 120.87(15) . . ?
C12 C11 C10 122.00(13) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?

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
O1 C1 N1 N2 178.64(12) . . . . ?
C2 C1 N1 N2 -0.53(13) . . . . ?
O1 C1 N1 C18 0.3(2) . . . . ?
C2 C1 N1 C18 -178.83(12) . . . . ?
C1 N1 N2 N3 0.11(13) . . . . ?
C18 N1 N2 N3 178.60(10) . . . . ?
O1 C1 C2 N3 -178.36(13) . . . . ?
N1 C1 C2 N3 0.73(12) . . . . ?
O1 C1 C2 C3 2.2(2) . . . . ?
N1 C1 C2 C3 -178.75(12) . . . . ?
N1 N2 N3 C2 0.41(14) . . . . ?
N1 N2 N3 C9 176.79(10) . . . . ?
C1 C2 N3 N2 -0.76(14) . . . . ?
C3 C2 N3 N2 178.73(11) . . . . ?
C1 C2 N3 C9 -176.65(11) . . . . ?
C3 C2 N3 C9 2.8(2) . . . . ?
N3 C2 C3 C8 44.0(2) . . . . ?
C1 C2 C3 C8 -136.57(15) . . . . ?
N3 C2 C3 C4 -138.57(14) . . . . ?
C1 C2 C3 C4 40.81(19) . . . . ?
C8 C3 C4 C5 -1.2(2) . . . . ?
C2 C3 C4 C5 -178.68(15) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C4 C3 C8 C7 1.1(2) . . . . ?
C2 C3 C8 C7 178.49(14) . . . . ?
N2 N3 C9 C10 83.75(14) . . . . ?
C2 N3 C9 C10 -100.44(15) . . . . ?
N2 N3 C9 C14 -95.69(13) . . . . ?
C2 N3 C9 C14 80.12(16) . . . . ?
C14 C9 C10 C11 -1.87(18) . . . . ?
N3 C9 C10 C11 178.72(11) . . . . ?
C14 C9 C10 C15 -179.76(12) . . . . ?
N3 C9 C10 C15 0.83(18) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C18 0.4(3) . . . . ?
C20 C19 C18 C23 0.8(3) . . . . ?
C20 C19 C18 N1 179.29(15) . . . . ?
C22 C23 C18 C19 -0.7(2) . . . . ?
C22 C23 C18 N1 -179.15(14) . . . . ?
N2 N1 C18 C19 -16.79(18) . . . . ?
C1 N1 C18 C19 161.45(14) . . . . ?
N2 N1 C18 C23 161.66(13) . . . . ?
C1 N1 C18 C23 -20.1(2) . . . . ?
C10 C9 C14 C13 1.58(18) . . . . ?
N3 C9 C14 C13 -179.00(11) . . . . ?
C10 C9 C14 C17 -178.62(12) . . . . ?
N3 C9 C14 C17 0.80(17) . . . . ?
C9 C14 C13 C12 0.42(19) . . . . ?
C17 C14 C13 C12 -179.38(12) . . . . ?
C14 C13 C12 C11 -2.0(2) . . . . ?
C14 C13 C12 C16 177.97(14) . . . . ?
C13 C12 C11 C10 1.7(2) . . . . ?
C16 C12 C11 C10 -178.29(14) . . . . ?
C9 C10 C11 C12 0.19(19) . . . . ?
C15 C10 C11 C12 178.12(12) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_wl453
_database_code_depnum_ccdc_archive 'CCDC 2104502'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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      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                   25.226(9)
_cell_length_b                   45.845(16)
_cell_length_c                   7.020(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8119(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    44891
_cell_measurement_theta_min      3.744
_cell_measurement_theta_max      27.505

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_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          0.2
_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  0.6568
_exptl_absorpt_correction_T_max  0.7282
_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            44891
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.744
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4628
_reflns_number_gt                3419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    '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)+(0.0094P)²+2.6764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00117(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4628
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 -0.31147(8) -0.06616(4) 0.7748(3) 0.0392(5) Uani 1 1 d . . . . .
C1 C -0.45778(9) -0.11566(5) 0.6561(4) 0.0350(5) Uani 1 1 d . . . . .
H1A H -0.462144 -0.095095 0.661485 0.042 Uiso 1 1 calc R U . . .
N2 N -0.30990(9) -0.03732(4) 0.7406(3) 0.0408(5) Uani 1 1 d . . . . .
C2 C -0.50179(10) -0.13324(6) 0.6348(4) 0.0417(6) Uani 1 1 d . . . . .
H2A H -0.535945 -0.124563 0.628307 0.050 Uiso 1 1 calc R U . . .
C3 C -0.49714(11) -0.16318(6) 0.6229(4) 0.0449(7) Uani 1 1 d . . . . .
H3A H -0.527697 -0.175063 0.607604 0.054 Uiso 1 1 calc R U . . .
N3 N -0.35067(8) -0.03344(4) 0.6232(3) 0.0343(5) Uani 1 1 d . . . . .
C4 C -0.44775(11) -0.17546(5) 0.6333(4) 0.0447(7) Uani 1 1 d . . . . .
H4A H -0.443942 -0.196019 0.623622 0.054 Uiso 1 1 calc R U . . .
C5 C -0.40349(10) -0.15821(5) 0.6578(4) 0.0400(6) Uani 1 1 d . . . . .
H5A H -0.369740 -0.167296 0.666765 0.048 Uiso 1 1 calc R U . . .
C6 C -0.40655(9) -0.12763(5) 0.6700(3) 0.0314(5) Uani 1 1 d . . . . .
C7 C -0.35921(10) -0.11092(5) 0.7050(4) 0.0346(6) Uani 1 1 d . . . . .
H7 H -0.3248(11) -0.1209(6) 0.763(4) 0.056(8) Uiso 1 1 d . . . . .
C8 C -0.35198(9) -0.08116(5) 0.6826(3) 0.0335(6) Uani 1 1 d . . . . .
C9 C -0.37759(9) -0.05845(5) 0.5783(3) 0.0312(6) Uani 1 1 d . . . . .
C10 C -0.41493(9) -0.06032(5) 0.4178(3) 0.0310(5) Uani 1 1 d . . . . .
C11 C -0.40923(10) -0.08316(5) 0.2885(3) 0.0365(6) Uani 1 1 d . . . . .
H11A H -0.382058 -0.097201 0.307819 0.044 Uiso 1 1 calc R U . . .
C12 C -0.44225(10) -0.08578(6) 0.1329(4) 0.0431(6) Uani 1 1 d . . . . .
H12A H -0.437195 -0.101254 0.044799 0.052 Uiso 1 1 calc R U . . .
C13 C -0.48267(11) -0.06591(6) 0.1052(4) 0.0481(7) Uani 1 1 d . . . . .
H13A H -0.505693 -0.067775 -0.001184 0.058 Uiso 1 1 calc R U . . .
C14 C -0.48939(11) -0.04342(6) 0.2325(4) 0.0446(7) Uani 1 1 d . . . . .
H14A H -0.517162 -0.029738 0.213219 0.054 Uiso 1 1 calc R U . . .
C15 C -0.45615(10) -0.04042(5) 0.3889(4) 0.0375(6) Uani 1 1 d . . . . .
H15A H -0.461412 -0.024858 0.476231 0.045 Uiso 1 1 calc R U . . .
C16 C -0.36187(9) -0.00395(5) 0.5628(4) 0.0353(6) Uani 1 1 d . . . . .
C17 C -0.33890(9) 0.00649(5) 0.3969(4) 0.0367(6) Uani 1 1 d . . . . .
C18 C -0.35031(10) 0.03529(5) 0.3462(4) 0.0397(6) Uani 1 1 d . . . . .
H18A H -0.334865 0.043100 0.233870 0.048 Uiso 1 1 calc R U . . .
C19 C -0.38322(11) 0.05274(5) 0.4539(4) 0.0430(7) Uani 1 1 d . . . . .
C20 C -0.40645(10) 0.04081(5) 0.6163(4) 0.0445(7) Uani 1 1 d . . . . .
H20A H -0.430389 0.052402 0.688313 0.053 Uiso 1 1 calc R U . . .
C21 C -0.39589(10) 0.01274(5) 0.6762(4) 0.0393(6) Uani 1 1 d . . . . .
C22 C -0.30351(11) -0.01212(6) 0.2740(4) 0.0466(7) Uani 1 1 d . . . . .
H22A H -0.274441 -0.019933 0.351258 0.070 Uiso 1 1 calc R U . . .
H22B H -0.288947 -0.000260 0.170310 0.070 Uiso 1 1 calc R U . . .
H22C H -0.324126 -0.028277 0.220411 0.070 Uiso 1 1 calc R U . . .
C23 C -0.39343(13) 0.08416(5) 0.4015(5) 0.0573(8) Uani 1 1 d . . . . .
H23A H -0.431680 0.087362 0.388719 0.086 Uiso 1 1 calc R U . . .
H23B H -0.375921 0.088612 0.280305 0.086 Uiso 1 1 calc R U . . .
H23C H -0.379335 0.096918 0.501375 0.086 Uiso 1 1 calc R U . . .
C24 C -0.41945(13) 0.00066(6) 0.8575(4) 0.0574(8) Uani 1 1 d . . . . .
H24A H -0.448276 0.013392 0.900522 0.086 Uiso 1 1 calc R U . . .
H24B H -0.391996 -0.000284 0.956114 0.086 Uiso 1 1 calc R U . . .
H24C H -0.433365 -0.018954 0.833635 0.086 Uiso 1 1 calc R U . . .
C25 C -0.27082(12) -0.07924(6) 0.8937(5) 0.0568(8) Uani 1 1 d . . . . .
H25A H -0.287519 -0.091719 0.989862 0.085 Uiso 1 1 calc R U . . .
H25B H -0.250471 -0.063830 0.957121 0.085 Uiso 1 1 calc R U . . .
H25C H -0.247019 -0.090991 0.814470 0.085 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 1.344(3) . ?
N1 C8 1.392(3) . ?
N1 C25 1.452(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.407(3) . ?
C1 H1A 0.9500 . ?
N2 N3 1.330(3) . ?
C2 C3 1.380(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.369(4) . ?
C3 H3A 0.9500 . ?
N3 C9 1.370(3) . ?
N3 C16 1.445(3) . ?
C4 C5 1.379(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.406(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.440(3) . ?
C7 C8 1.385(3) . ?
C7 H7 1.06(3) . ?
C8 C9 1.428(3) . ?
C9 C10 1.471(3) . ?
C10 C11 1.394(3) . ?
C10 C15 1.398(3) . ?
C11 C12 1.379(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.375(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.388(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.386(4) . ?
C16 C21 1.399(4) . ?
C17 C18 1.397(3) . ?
C17 C22 1.506(3) . ?
C18 C19 1.379(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.394(4) . ?
C19 C23 1.509(3) . ?
C20 C21 1.379(4) . ?
C20 H20A 0.9500 . ?
C21 C24 1.510(4) . ?
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 C8 115.12(19) . . ?
N2 N1 C25 119.2(2) . . ?
C8 N1 C25 125.6(2) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 H1A 119.4 . . ?
C6 C1 H1A 119.4 . . ?
N3 N2 N1 102.70(18) . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
N2 N3 C9 114.47(19) . . ?
N2 N3 C16 117.29(18) . . ?
C9 N3 C16 128.2(2) . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C5 C6 C1 115.8(2) . . ?
C5 C6 C7 119.7(2) . . ?
C1 C6 C7 124.5(2) . . ?
C8 C7 C6 127.9(2) . . ?
C8 C7 H7 111.0(14) . . ?
C6 C7 H7 121.0(14) . . ?
C7 C8 N1 122.1(2) . . ?
C7 C8 C9 135.8(2) . . ?
N1 C8 C9 102.15(19) . . ?
N3 C9 C8 105.5(2) . . ?
N3 C9 C10 122.9(2) . . ?
C8 C9 C10 129.8(2) . . ?
C11 C10 C15 118.2(2) . . ?
C11 C10 C9 118.5(2) . . ?
C15 C10 C9 123.3(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C14 C15 C10 120.0(2) . . ?
C14 C15 H15A 120.0 . . ?
C10 C15 H15A 120.0 . . ?
C17 C16 C21 123.1(2) . . ?
C17 C16 N3 119.2(2) . . ?
C21 C16 N3 117.7(2) . . ?
C16 C17 C18 117.0(2) . . ?
C16 C17 C22 122.2(2) . . ?
C18 C17 C22 120.8(2) . . ?
C19 C18 C17 122.2(3) . . ?
C19 C18 H18A 118.9 . . ?
C17 C18 H18A 118.9 . . ?
C18 C19 C20 118.3(2) . . ?
C18 C19 C23 121.6(3) . . ?
C20 C19 C23 120.2(3) . . ?
C21 C20 C19 122.3(2) . . ?
C21 C20 H20A 118.9 . . ?
C19 C20 H20A 118.9 . . ?
C20 C21 C16 117.1(2) . . ?
C20 C21 C24 121.5(2) . . ?
C16 C21 C24 121.4(2) . . ?
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
C8 N1 N2 N3 0.2(3) . . . . ?
C25 N1 N2 N3 177.4(2) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
N1 N2 N3 C9 -1.1(3) . . . . ?
N1 N2 N3 C16 177.6(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 176.9(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C1 C6 C7 -175.6(2) . . . . ?
C5 C6 C7 C8 165.3(2) . . . . ?
C1 C6 C7 C8 -18.3(4) . . . . ?
C6 C7 C8 N1 159.3(2) . . . . ?
C6 C7 C8 C9 -20.7(5) . . . . ?
N2 N1 C8 C7 -179.3(2) . . . . ?
C25 N1 C8 C7 3.7(4) . . . . ?
N2 N1 C8 C9 0.7(3) . . . . ?
C25 N1 C8 C9 -176.3(3) . . . . ?
N2 N3 C9 C8 1.6(3) . . . . ?
C16 N3 C9 C8 -177.0(2) . . . . ?
N2 N3 C9 C10 -164.6(2) . . . . ?
C16 N3 C9 C10 16.8(4) . . . . ?
C7 C8 C9 N3 178.7(3) . . . . ?
N1 C8 C9 N3 -1.2(2) . . . . ?
C7 C8 C9 C10 -16.4(5) . . . . ?
N1 C8 C9 C10 163.7(2) . . . . ?
N3 C9 C10 C11 129.5(2) . . . . ?
C8 C9 C10 C11 -33.1(4) . . . . ?
N3 C9 C10 C15 -50.9(3) . . . . ?
C8 C9 C10 C15 146.5(3) . . . . ?
C15 C10 C11 C12 1.7(3) . . . . ?
C9 C10 C11 C12 -178.6(2) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C10 0.5(4) . . . . ?
C11 C10 C15 C14 -1.2(4) . . . . ?
C9 C10 C15 C14 179.1(2) . . . . ?
N2 N3 C16 C17 91.4(3) . . . . ?
C9 N3 C16 C17 -90.0(3) . . . . ?
N2 N3 C16 C21 -88.7(3) . . . . ?
C9 N3 C16 C21 89.8(3) . . . . ?
C21 C16 C17 C18 1.1(4) . . . . ?
N3 C16 C17 C18 -179.0(2) . . . . ?
C21 C16 C17 C22 -178.3(2) . . . . ?
N3 C16 C17 C22 1.5(4) . . . . ?
C16 C17 C18 C19 -0.6(4) . . . . ?
C22 C17 C18 C19 178.9(2) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
C17 C18 C19 C23 177.5(3) . . . . ?
C18 C19 C20 C21 2.7(4) . . . . ?
C23 C19 C20 C21 -176.1(3) . . . . ?
C19 C20 C21 C16 -2.2(4) . . . . ?
C19 C20 C21 C24 177.1(3) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
N3 C16 C21 C20 -179.7(2) . . . . ?
C17 C16 C21 C24 -179.1(2) . . . . ?
N3 C16 C21 C24 1.0(4) . . . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_wl507
_database_code_depnum_ccdc_archive 'CCDC 2104499'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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 Cl2 N3 O2'
_chemical_formula_weight         470.38

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'
O O 0.0106 0.0060 '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                   11.279(3)
_cell_length_b                   11.539(4)
_cell_length_c                   11.879(4)
_cell_angle_alpha                93.664(11)
_cell_angle_beta                 116.197(9)
_cell_angle_gamma                115.492(9)
_cell_volume                     1189.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    41856
_cell_measurement_theta_min      2.343
_cell_measurement_theta_max      27.988

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.300
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6837
_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            41856
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.343
_diffrn_reflns_theta_max         27.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5673
_reflns_number_gt                4429
_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)+(0.0645P)²+0.3801P] 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         5673
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Cl1 Cl 0.44484(5) 0.12635(5) 0.49302(5) 0.04883(15) Uani 1 1 d . . . . .
O1 O 0.20471(17) 0.46670(14) 0.28955(12) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.25491(14) 0.48437(13) 0.64249(12) 0.0259(3) Uani 1 1 d . . . . .
C1 C -0.0332(2) 0.14832(18) 0.02542(18) 0.0374(4) Uani 1 1 d . . . . .
H1 H 0.015231 0.100654 0.067419 0.045 Uiso 1 1 calc R U . . .
Cl2 Cl 0.35183(6) 0.21355(5) 0.65993(5) 0.05019(15) Uani 1 1 d . . . . .
O2 O 0.19901(13) 0.27283(13) 0.29445(12) 0.0394(3) Uani 1 1 d . . . . .
N2 N 0.33637(15) 0.54171(14) 0.77247(12) 0.0289(3) Uani 1 1 d . . . . .
C2 C -0.1518(2) 0.0890(2) -0.1069(2) 0.0459(5) Uani 1 1 d . . . . .
H2 H -0.184035 0.001517 -0.154699 0.055 Uiso 1 1 calc R U . . .
N3 N 0.47937(14) 0.61352(14) 0.79880(12) 0.0280(3) Uani 1 1 d . . . . .
C3 C -0.2213(3) 0.1574(2) -0.1673(2) 0.0594(6) Uani 1 1 d . . . . .
H3 H -0.300904 0.117871 -0.257835 0.071 Uiso 1 1 calc R U . . .
C4 C -0.1769(3) 0.2837(3) -0.0979(2) 0.0819(9) Uani 1 1 d . . . . .
H4 H -0.227550 0.329806 -0.139921 0.098 Uiso 1 1 calc R U . . .
C5 C -0.0582(3) 0.3430(2) 0.0333(2) 0.0627(7) Uani 1 1 d . . . . .
H5 H -0.026732 0.430552 0.080352 0.075 Uiso 1 1 calc R U . . .
C6 C 0.0151(2) 0.27624(18) 0.09657(16) 0.0346(4) Uani 1 1 d . . . . .
C7 C 0.1514(2) 0.34482(17) 0.24030(17) 0.0326(3) Uani 1 1 d . . . . .
C8 C 0.34288(18) 0.51809(16) 0.58706(15) 0.0283(3) Uani 1 1 d . . . . .
H8 H 0.309187 0.488973 0.496262 0.034 Uiso 1 1 calc R U . . .
C9 C 0.48984(18) 0.60267(17) 0.68971(15) 0.0296(3) Uani 1 1 d . . . . .
H9 H 0.580444 0.645046 0.685631 0.035 Uiso 1 1 calc R U . . .
C10 C 0.60410(17) 0.69622(16) 0.93319(14) 0.0283(3) Uani 1 1 d . . . . .
C11 C 0.62447(19) 0.82084(18) 0.98141(16) 0.0351(4) Uani 1 1 d . . . . .
C12 C 0.7509(2) 0.90191(18) 1.10711(16) 0.0363(4) Uani 1 1 d . . . . .
H12 H 0.768579 0.987669 1.143125 0.044 Uiso 1 1 calc R U . . .
C13 C 0.85217(18) 0.86124(17) 1.18169(15) 0.0321(3) Uani 1 1 d . . . . .
C14 C 0.82351(18) 0.73442(17) 1.12936(15) 0.0312(3) Uani 1 1 d . . . . .
H14 H 0.891031 0.705331 1.180947 0.037 Uiso 1 1 calc R U . . .
C15 C 0.69929(18) 0.64858(16) 1.00400(15) 0.0285(3) Uani 1 1 d . . . . .
C16 C 0.5167(3) 0.8671(2) 0.9015(2) 0.0552(6) Uani 1 1 d . . . . .
H16A H 0.495138 0.848544 0.810797 0.083 Uiso 1 1 calc R U . . .
H16B H 0.564442 0.964383 0.941090 0.083 Uiso 1 1 calc R U . . .
H16C H 0.420353 0.818360 0.900633 0.083 Uiso 1 1 calc R U . . .
C17 C 0.9914(2) 0.95415(19) 1.31532(17) 0.0410(4) Uani 1 1 d . . . . .
H17A H 1.057813 0.915661 1.347637 0.062 Uiso 1 1 calc R U . . .
H17B H 0.958556 0.964512 1.377280 0.062 Uiso 1 1 calc R U . . .
H17C H 1.048350 1.042727 1.308018 0.062 Uiso 1 1 calc R U . . .
C18 C 0.6707(2) 0.51187(18) 0.94904(17) 0.0372(4) Uani 1 1 d . . . . .
H18A H 0.565206 0.442458 0.920477 0.056 Uiso 1 1 calc R U . . .
H18B H 0.743302 0.493486 1.017438 0.056 Uiso 1 1 calc R U . . .
H18C H 0.684823 0.510606 0.873385 0.056 Uiso 1 1 calc R U . . .
C19 C 0.09090(17) 0.39496(16) 0.57845(15) 0.0265(3) Uani 1 1 d . . . . .
C20 C 0.01835(18) 0.28697(17) 0.46792(16) 0.0322(3) Uani 1 1 d . . . . .
H20 H 0.074299 0.273137 0.433165 0.039 Uiso 1 1 calc R U . . .
C21 C -0.1391(2) 0.19921(19) 0.40920(17) 0.0386(4) Uani 1 1 d . . . . .
H21 H -0.192181 0.124870 0.332381 0.046 Uiso 1 1 calc R U . . .
C22 C -0.21914(19) 0.21922(19) 0.46168(17) 0.0381(4) Uani 1 1 d . . . . .
H22 H -0.326173 0.157203 0.421970 0.046 Uiso 1 1 calc R U . . .
C23 C -0.14444(19) 0.32889(19) 0.57159(17) 0.0352(4) Uani 1 1 d . . . . .
H23 H -0.200409 0.342388 0.606508 0.042 Uiso 1 1 calc R U . . .
C24 C 0.01248(19) 0.41933(17) 0.63091(16) 0.0305(3) Uani 1 1 d . . . . .
H24 H 0.064730 0.495849 0.705460 0.037 Uiso 1 1 calc R U . . .
C25 C 0.4327(2) 0.25926(18) 0.56045(17) 0.0355(4) Uani 1 1 d . . . . .
H25A H 0.536852 0.340493 0.614300 0.043 Uiso 1 1 calc R U . . .
H25B H 0.368624 0.282215 0.487812 0.043 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 C25 1.7701(19) . ?
O1 C7 1.240(2) . ?
N1 N2 1.3265(18) . ?
N1 C8 1.359(2) . ?
N1 C19 1.4421(19) . ?
C1 C6 1.390(2) . ?
C1 C2 1.396(3) . ?
C1 H1 0.9500 . ?
Cl2 C25 1.7674(18) . ?
O2 C7 1.241(2) . ?
N2 N3 1.3256(19) . ?
C2 C3 1.364(3) . ?
C2 H2 0.9500 . ?
N3 C9 1.355(2) . ?
N3 C10 1.451(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.539(2) . ?
C8 C9 1.363(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.390(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.506(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C13 C17 1.506(2) . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 C18 1.504(2) . ?
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 1.382(2) . ?
C19 C24 1.389(2) . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 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 112.98(13) . . ?
N2 N1 C19 118.70(12) . . ?
C8 N1 C19 128.31(13) . . ?
C6 C1 C2 120.83(17) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
N3 N2 N1 103.32(12) . . ?
C3 C2 C1 119.63(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N2 N3 C9 113.07(13) . . ?
N2 N3 C10 119.96(12) . . ?
C9 N3 C10 126.93(13) . . ?
C2 C3 C4 120.50(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.41(16) . . ?
C5 C6 C7 120.65(16) . . ?
C1 C6 C7 120.88(15) . . ?
O1 C7 O2 126.51(17) . . ?
O1 C7 C6 117.02(15) . . ?
O2 C7 C6 116.45(15) . . ?
N1 C8 C9 105.20(14) . . ?
N1 C8 H8 127.4 . . ?
C9 C8 H8 127.4 . . ?
N3 C9 C8 105.44(14) . . ?
N3 C9 H9 127.3 . . ?
C8 C9 H9 127.3 . . ?
C15 C10 C11 124.09(14) . . ?
C15 C10 N3 117.99(14) . . ?
C11 C10 N3 117.88(14) . . ?
C12 C11 C10 116.68(15) . . ?
C12 C11 C16 121.23(16) . . ?
C10 C11 C16 122.09(16) . . ?
C13 C12 C11 121.95(16) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 118.62(15) . . ?
C12 C13 C17 120.41(16) . . ?
C14 C13 C17 120.96(16) . . ?
C13 C14 C15 122.26(15) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 116.37(15) . . ?
C10 C15 C18 122.22(14) . . ?
C14 C15 C18 121.40(15) . . ?
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 . . ?
C20 C19 C24 122.61(15) . . ?
C20 C19 N1 118.41(14) . . ?
C24 C19 N1 118.97(14) . . ?
C19 C20 C21 117.91(15) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C22 C21 C20 120.58(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.50(16) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 120.03(15) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 118.32(16) . . ?
C19 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
Cl2 C25 Cl1 111.34(10) . . ?
Cl2 C25 H25A 109.4 . . ?
Cl1 C25 H25A 109.4 . . ?
Cl2 C25 H25B 109.4 . . ?
Cl1 C25 H25B 109.4 . . ?
H25A C25 H25B 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
C8 N1 N2 N3 0.11(16) . . . . ?
C19 N1 N2 N3 178.86(12) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
N1 N2 N3 C9 -0.12(17) . . . . ?
N1 N2 N3 C10 177.84(13) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 177.3(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C6 C7 -176.78(16) . . . . ?
C5 C6 C7 O1 -9.4(3) . . . . ?
C1 C6 C7 O1 167.80(17) . . . . ?
C5 C6 C7 O2 171.96(19) . . . . ?
C1 C6 C7 O2 -10.8(2) . . . . ?
N2 N1 C8 C9 -0.06(18) . . . . ?
C19 N1 C8 C9 -178.66(14) . . . . ?
N2 N3 C9 C8 0.09(18) . . . . ?
C10 N3 C9 C8 -177.70(15) . . . . ?
N1 C8 C9 N3 -0.02(17) . . . . ?
N2 N3 C10 C15 103.36(17) . . . . ?
C9 N3 C10 C15 -79.0(2) . . . . ?
N2 N3 C10 C11 -79.03(19) . . . . ?
C9 N3 C10 C11 98.6(2) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
N3 C10 C11 C12 -175.81(15) . . . . ?
C15 C10 C11 C16 -179.07(18) . . . . ?
N3 C10 C11 C16 3.5(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C16 C11 C12 C13 -179.45(18) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C11 C12 C13 C17 177.56(16) . . . . ?
C12 C13 C14 C15 1.6(2) . . . . ?
C17 C13 C14 C15 -177.36(15) . . . . ?
C11 C10 C15 C14 -1.5(2) . . . . ?
N3 C10 C15 C14 175.98(13) . . . . ?
C11 C10 C15 C18 178.55(16) . . . . ?
N3 C10 C15 C18 -4.0(2) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C13 C14 C15 C18 179.78(15) . . . . ?
N2 N1 C19 C20 -147.27(15) . . . . ?
C8 N1 C19 C20 31.3(2) . . . . ?
N2 N1 C19 C24 31.8(2) . . . . ?
C8 N1 C19 C24 -149.64(16) . . . . ?
C24 C19 C20 C21 -0.9(2) . . . . ?
N1 C19 C20 C21 178.20(14) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 1.6(3) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C20 C19 C24 C23 1.9(2) . . . . ?
N1 C19 C24 C23 -177.20(14) . . . . ?
C22 C23 C24 C19 -1.1(2) . . . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.390
_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_wl524
_database_code_depnum_ccdc_archive 'CCDC 2104503'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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            'C30 H27 N3'
_chemical_formula_weight         429.54

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                   8.500(2)
_cell_length_b                   24.610(8)
_cell_length_c                   12.044(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.619(15)
_cell_angle_gamma                90
_cell_volume                     2358.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    30484
_cell_measurement_theta_min      3.050
_cell_measurement_theta_max      27.510

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_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  0.6994
_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            30484
_diffrn_reflns_av_unetI/netI     0.1031
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.050
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5388
_reflns_number_gt                3265
_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)+(0.0411P)²+0.2684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0123(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5388
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.26089(18) 0.61037(6) 0.50755(13) 0.0254(4) Uani 1 1 d . . . . .
C1 C 0.3531(2) 0.71002(8) 0.20243(17) 0.0306(5) Uani 1 1 d . . . . .
H1 H 0.447667 0.732614 0.239682 0.037 Uiso 1 1 calc R U . . .
N2 N 0.31182(18) 0.57968(7) 0.61034(13) 0.0284(4) Uani 1 1 d . . . . .
C2 C 0.2731(3) 0.71351(9) 0.08081(18) 0.0366(5) Uani 1 1 d . . . . .
H2 H 0.313708 0.738169 0.036460 0.044 Uiso 1 1 calc R U . . .
N3 N 0.47252(18) 0.59385(6) 0.66192(13) 0.0248(4) Uani 1 1 d . . . . .
C3 C 0.1347(3) 0.68147(9) 0.02310(18) 0.0392(5) Uani 1 1 d . . . . .
H3 H 0.078480 0.684394 -0.060197 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0798(2) 0.64508(9) 0.08917(17) 0.0353(5) Uani 1 1 d . . . . .
H4 H -0.014150 0.622488 0.050362 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1597(2) 0.64101(8) 0.21137(16) 0.0285(4) Uani 1 1 d . . . . .
H5 H 0.119603 0.615409 0.254148 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2989(2) 0.67390(7) 0.27347(16) 0.0245(4) Uani 1 1 d . . . . .
C7 C 0.3981(2) 0.67198(8) 0.39817(16) 0.0254(4) Uani 1 1 d . . . . .
H7 H 0.503(2) 0.6925(8) 0.4192(16) 0.031(5) Uiso 1 1 d . . . . .
C8 C 0.3907(2) 0.64149(7) 0.49333(16) 0.0235(4) Uani 1 1 d . . . . .
C9 C 0.5283(2) 0.63073(7) 0.60122(16) 0.0240(4) Uani 1 1 d . . . . .
C10 C 0.7014(2) 0.65195(8) 0.63983(15) 0.0254(4) Uani 1 1 d . . . . .
C11 C 0.7280(2) 0.70792(8) 0.63631(17) 0.0322(5) Uani 1 1 d . . . . .
H11 H 0.634643 0.731985 0.613531 0.039 Uiso 1 1 calc R U . . .
C12 C 0.8898(3) 0.72866(9) 0.66583(18) 0.0383(5) Uani 1 1 d . . . . .
H12 H 0.906688 0.766727 0.663221 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0261(3) 0.69371(9) 0.69902(18) 0.0386(5) Uani 1 1 d . . . . .
H13 H 1.136713 0.707826 0.719181 0.046 Uiso 1 1 calc R U . . .
C14 C 1.0017(2) 0.63834(9) 0.70289(17) 0.0356(5) Uani 1 1 d . . . . .
H14 H 1.095595 0.614476 0.725842 0.043 Uiso 1 1 calc R U . . .
C15 C 0.8398(2) 0.61741(8) 0.67322(17) 0.0304(5) Uani 1 1 d . . . . .
H15 H 0.823829 0.579286 0.675798 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5631(2) 0.56764(8) 0.77451(16) 0.0247(4) Uani 1 1 d . . . . .
C17 C 0.6174(2) 0.51434(8) 0.77220(17) 0.0283(4) Uani 1 1 d . . . . .
C18 C 0.6954(2) 0.48883(9) 0.88082(17) 0.0346(5) Uani 1 1 d . . . . .
H18 H 0.732908 0.452411 0.881764 0.041 Uiso 1 1 calc R U . . .
C19 C 0.7204(3) 0.51500(9) 0.98840(17) 0.0361(5) Uani 1 1 d . . . . .
C20 C 0.6641(2) 0.56825(8) 0.98541(17) 0.0349(5) Uani 1 1 d . . . . .
H20 H 0.680782 0.586426 1.058264 0.042 Uiso 1 1 calc R U . . .
C21 C 0.5841(2) 0.59591(8) 0.87951(17) 0.0285(4) Uani 1 1 d . . . . .
C22 C 0.5977(3) 0.48482(8) 0.65839(17) 0.0370(5) Uani 1 1 d . . . . .
H22A H 0.485339 0.491723 0.600316 0.055 Uiso 1 1 calc R U . . .
H22B H 0.612428 0.445712 0.673961 0.055 Uiso 1 1 calc R U . . .
H22C H 0.682706 0.497827 0.626926 0.055 Uiso 1 1 calc R U . . .
C23 C 0.8059(3) 0.48545(11) 1.10360(19) 0.0546(7) Uani 1 1 d . . . . .
H23A H 0.726857 0.481134 1.145776 0.082 Uiso 1 1 calc R U . . .
H23B H 0.903547 0.506428 1.152774 0.082 Uiso 1 1 calc R U . . .
H23C H 0.842729 0.449583 1.087163 0.082 Uiso 1 1 calc R U . . .
C24 C 0.5248(3) 0.65358(9) 0.8795(2) 0.0449(6) Uani 1 1 d . . . . .
H24A H 0.608907 0.678585 0.870109 0.067 Uiso 1 1 calc R U . . .
H24B H 0.508805 0.661081 0.954792 0.067 Uiso 1 1 calc R U . . .
H24C H 0.417970 0.658587 0.813774 0.067 Uiso 1 1 calc R U . . .
C25 C 0.0835(2) 0.61219(7) 0.44492(16) 0.0249(4) Uani 1 1 d . . . . .
C26 C 0.0029(2) 0.66164(8) 0.41047(17) 0.0309(5) Uani 1 1 d . . . . .
H26 H 0.065079 0.694593 0.426059 0.037 Uiso 1 1 calc R U . . .
C27 C -0.1691(2) 0.66219(9) 0.35316(18) 0.0368(5) Uani 1 1 d . . . . .
H27 H -0.225705 0.695871 0.329734 0.044 Uiso 1 1 calc R U . . .
C28 C -0.2602(2) 0.61431(9) 0.32938(18) 0.0369(5) Uani 1 1 d . . . . .
H28 H -0.378523 0.615202 0.289527 0.044 Uiso 1 1 calc R U . . .
C29 C -0.1787(2) 0.56507(9) 0.36375(18) 0.0356(5) Uani 1 1 d . . . . .
H29 H -0.241063 0.532156 0.347561 0.043 Uiso 1 1 calc R U . . .
C30 C -0.0057(2) 0.56386(8) 0.42191(17) 0.0298(5) Uani 1 1 d . . . . .
H30 H 0.050959 0.530202 0.445666 0.036 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 1.383(2) . ?
N1 C8 1.402(2) . ?
N1 C25 1.429(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.419(2) . ?
C1 H1 0.9500 . ?
N2 N3 1.333(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
N3 C9 1.352(2) . ?
N3 C16 1.453(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.411(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.441(3) . ?
C7 C8 1.390(3) . ?
C7 H7 0.979(18) . ?
C8 C9 1.434(2) . ?
C9 C10 1.474(2) . ?
C10 C15 1.391(3) . ?
C10 C11 1.399(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.394(3) . ?
C16 C21 1.399(3) . ?
C17 C18 1.391(3) . ?
C17 C22 1.508(3) . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(3) . ?
C19 C23 1.507(3) . ?
C20 C21 1.393(3) . ?
C20 H20 0.9500 . ?
C21 C24 1.506(3) . ?
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 C30 1.385(3) . ?
C25 C26 1.386(3) . ?
C26 C27 1.380(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.383(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.389(3) . ?
C29 H29 0.9500 . ?
C30 H30 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 113.32(14) . . ?
N2 N1 C25 115.40(13) . . ?
C8 N1 C25 130.36(15) . . ?
C2 C1 C6 122.32(19) . . ?
C2 C1 H1 118.8 . . ?
C6 C1 H1 118.8 . . ?
N3 N2 N1 102.75(13) . . ?
C3 C2 C1 120.71(19) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N2 N3 C9 114.88(15) . . ?
N2 N3 C16 115.97(14) . . ?
C9 N3 C16 129.15(15) . . ?
C2 C3 C4 118.65(19) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 121.72(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 115.43(17) . . ?
C5 C6 C7 127.41(16) . . ?
C1 C6 C7 116.98(17) . . ?
C8 C7 C6 134.19(18) . . ?
C8 C7 H7 111.6(11) . . ?
C6 C7 H7 113.5(11) . . ?
C7 C8 N1 131.44(17) . . ?
C7 C8 C9 125.99(16) . . ?
N1 C8 C9 102.37(15) . . ?
N3 C9 C8 106.55(15) . . ?
N3 C9 C10 124.65(16) . . ?
C8 C9 C10 128.72(15) . . ?
C15 C10 C11 118.76(17) . . ?
C15 C10 C9 121.57(17) . . ?
C11 C10 C9 119.56(17) . . ?
C12 C11 C10 120.64(19) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.14(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.45(19) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C21 123.25(17) . . ?
C17 C16 N3 117.99(16) . . ?
C21 C16 N3 118.68(16) . . ?
C18 C17 C16 117.22(18) . . ?
C18 C17 C22 120.08(18) . . ?
C16 C17 C22 122.69(17) . . ?
C17 C18 C19 122.12(19) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C18 118.19(18) . . ?
C20 C19 C23 121.88(19) . . ?
C18 C19 C23 119.9(2) . . ?
C19 C20 C21 122.43(18) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C16 116.78(17) . . ?
C20 C21 C24 121.03(17) . . ?
C16 C21 C24 122.19(17) . . ?
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 . . ?
C30 C25 C26 121.06(17) . . ?
C30 C25 N1 118.68(16) . . ?
C26 C25 N1 120.25(17) . . ?
C27 C26 C25 118.91(19) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C28 120.82(19) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C29 119.92(18) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 119.94(19) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C29 119.35(18) . . ?
C25 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?

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 2.50(19) . . . . ?
C25 N1 N2 N3 -167.66(14) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
N1 N2 N3 C9 -0.03(19) . . . . ?
N1 N2 N3 C16 -179.84(14) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -1.5(2) . . . . ?
C4 C5 C6 C7 -176.56(17) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C7 176.75(17) . . . . ?
C5 C6 C7 C8 -2.2(3) . . . . ?
C1 C6 C7 C8 -177.21(19) . . . . ?
C6 C7 C8 N1 -17.3(3) . . . . ?
C6 C7 C8 C9 156.52(19) . . . . ?
N2 N1 C8 C7 171.11(18) . . . . ?
C25 N1 C8 C7 -20.6(3) . . . . ?
N2 N1 C8 C9 -3.77(19) . . . . ?
C25 N1 C8 C9 164.54(17) . . . . ?
N2 N3 C9 C8 -2.3(2) . . . . ?
C16 N3 C9 C8 177.49(16) . . . . ?
N2 N3 C9 C10 -179.19(16) . . . . ?
C16 N3 C9 C10 0.6(3) . . . . ?
C7 C8 C9 N3 -171.78(17) . . . . ?
N1 C8 C9 N3 3.47(18) . . . . ?
C7 C8 C9 C10 4.9(3) . . . . ?
N1 C8 C9 C10 -179.80(17) . . . . ?
N3 C9 C10 C15 50.9(3) . . . . ?
C8 C9 C10 C15 -125.3(2) . . . . ?
N3 C9 C10 C11 -133.03(19) . . . . ?
C8 C9 C10 C11 50.8(3) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 C12 -176.32(17) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C11 C10 C15 C14 0.2(3) . . . . ?
C9 C10 C15 C14 176.33(17) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
N2 N3 C16 C17 77.7(2) . . . . ?
C9 N3 C16 C17 -102.1(2) . . . . ?
N2 N3 C16 C21 -99.15(19) . . . . ?
C9 N3 C16 C21 81.1(2) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
N3 C16 C17 C18 -176.46(16) . . . . ?
C21 C16 C17 C22 -178.43(17) . . . . ?
N3 C16 C17 C22 4.8(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C22 C17 C18 C19 178.28(18) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C17 C18 C19 C23 -179.9(2) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C23 C19 C20 C21 -179.7(2) . . . . ?
C19 C20 C21 C16 -0.3(3) . . . . ?
C19 C20 C21 C24 180.00(19) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
N3 C16 C21 C20 176.80(15) . . . . ?
C17 C16 C21 C24 179.79(18) . . . . ?
N3 C16 C21 C24 -3.5(3) . . . . ?
N2 N1 C25 C30 -49.1(2) . . . . ?
C8 N1 C25 C30 142.80(18) . . . . ?
N2 N1 C25 C26 129.57(17) . . . . ?
C8 N1 C25 C26 -38.5(3) . . . . ?
C30 C25 C26 C27 0.5(3) . . . . ?
N1 C25 C26 C27 -178.15(16) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C26 C27 C28 C29 0.3(3) . . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
C26 C25 C30 C29 -0.2(3) . . . . ?
N1 C25 C30 C29 178.41(16) . . . . ?
C28 C29 C30 C25 0.0(3) . . . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_wl483
_database_code_depnum_ccdc_archive 'CCDC 2104501'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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 O2'
_chemical_formula_weight         399.48

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'
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/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                   16.149(5)
_cell_length_b                   6.597(2)
_cell_length_c                   21.350(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.183(10)
_cell_angle_gamma                90
_cell_volume                     2205.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    72145
_cell_measurement_theta_min      3.241
_cell_measurement_theta_max      27.564

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_T_max  0.6946
_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            72145
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.241
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5074
_reflns_number_gt                3396
_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)+(0.0862P)²+0.7152P] 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         5074
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1734
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.36489(11) -0.4225(3) 0.49652(9) 0.0687(6) Uani 1 1 d . . . . .
N1 N 0.46394(10) 0.3080(2) 0.59882(7) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.19387(15) -0.0591(4) 0.44986(11) 0.0487(6) Uani 1 1 d . . . . .
H1 H 0.224591 0.050962 0.437764 0.058 Uiso 1 1 calc R U . . .
O2 O 0.36309(10) -0.1278(2) 0.44743(8) 0.0487(4) Uani 1 1 d . . . . .
N2 N 0.41957(10) 0.3096(2) 0.64317(7) 0.0299(4) Uani 1 1 d . . . . .
C2 C 0.10685(17) -0.0398(5) 0.44638(13) 0.0670(8) Uani 1 1 d . . . . .
H2 H 0.078360 0.084114 0.432312 0.080 Uiso 1 1 calc R U . . .
N3 N 0.45677(9) 0.4528(2) 0.68422(7) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.06247(16) -0.1989(6) 0.46315(15) 0.0802(10) Uani 1 1 d . . . . .
H3 H 0.003060 -0.185212 0.460134 0.096 Uiso 1 1 calc R U . . .
C4 C 0.10276(18) -0.3774(6) 0.48425(16) 0.0829(10) Uani 1 1 d . . . . .
H4 H 0.071454 -0.486704 0.496138 0.099 Uiso 1 1 calc R U . . .
C5 C 0.19009(15) -0.3991(4) 0.48830(12) 0.0601(7) Uani 1 1 d . . . . .
H5 H 0.218217 -0.523108 0.502843 0.072 Uiso 1 1 calc R U . . .
C6 C 0.23528(13) -0.2393(3) 0.47104(9) 0.0381(5) Uani 1 1 d . . . . .
C7 C 0.32914(13) -0.2646(3) 0.47212(9) 0.0370(5) Uani 1 1 d . . . . .
C8 C 0.52763(12) 0.4448(3) 0.61013(9) 0.0299(4) Uani 1 1 d . . . . .
H8 H 0.567006 0.469106 0.584423 0.036 Uiso 1 1 calc R U . . .
C9 C 0.52431(11) 0.5419(3) 0.66614(9) 0.0269(4) Uani 1 1 d . . . . .
C10 C 0.57770(11) 0.7056(3) 0.70132(9) 0.0281(4) Uani 1 1 d . . . . .
C11 C 0.60814(12) 0.8537(3) 0.66563(10) 0.0342(5) Uani 1 1 d . . . . .
H11 H 0.591958 0.849580 0.619760 0.041 Uiso 1 1 calc R U . . .
C12 C 0.66154(13) 1.0057(3) 0.69666(11) 0.0398(5) Uani 1 1 d . . . . .
H12 H 0.682129 1.105277 0.672115 0.048 Uiso 1 1 calc R U . . .
C13 C 0.68509(13) 1.0130(3) 0.76349(11) 0.0403(5) Uani 1 1 d . . . . .
H13 H 0.721730 1.117681 0.784836 0.048 Uiso 1 1 calc R U . . .
C14 C 0.65502(13) 0.8671(3) 0.79921(10) 0.0386(5) Uani 1 1 d . . . . .
H14 H 0.671114 0.872422 0.845065 0.046 Uiso 1 1 calc R U . . .
C15 C 0.60186(12) 0.7141(3) 0.76859(9) 0.0334(4) Uani 1 1 d . . . . .
H15 H 0.581733 0.614466 0.793411 0.040 Uiso 1 1 calc R U . . .
C16 C 0.41598(11) 0.5121(3) 0.73502(9) 0.0279(4) Uani 1 1 d . . . . .
C17 C 0.42869(12) 0.3958(3) 0.79063(9) 0.0315(4) Uani 1 1 d . . . . .
C18 C 0.39009(12) 0.4653(3) 0.83867(9) 0.0371(5) Uani 1 1 d . . . . .
H18 H 0.396988 0.389520 0.877443 0.045 Uiso 1 1 calc R U . . .
C19 C 0.34190(12) 0.6426(3) 0.83098(10) 0.0388(5) Uani 1 1 d . . . . .
C20 C 0.32862(12) 0.7465(3) 0.77330(10) 0.0397(5) Uani 1 1 d . . . . .
H20 H 0.293751 0.864301 0.767325 0.048 Uiso 1 1 calc R U . . .
C21 C 0.36469(12) 0.6841(3) 0.72349(10) 0.0341(5) Uani 1 1 d . . . . .
C22 C 0.48202(14) 0.2063(3) 0.79960(11) 0.0423(5) Uani 1 1 d . . . . .
H22A H 0.457089 0.108730 0.765593 0.063 Uiso 1 1 calc R U . . .
H22B H 0.483472 0.146949 0.841931 0.063 Uiso 1 1 calc R U . . .
H22C H 0.540258 0.239744 0.797118 0.063 Uiso 1 1 calc R U . . .
C23 C 0.30604(15) 0.7229(4) 0.88521(12) 0.0564(7) Uani 1 1 d . . . . .
H23A H 0.245361 0.754721 0.868524 0.085 Uiso 1 1 calc R U . . .
H23B H 0.337009 0.845867 0.903062 0.085 Uiso 1 1 calc R U . . .
H23C H 0.312517 0.620072 0.919205 0.085 Uiso 1 1 calc R U . . .
C24 C 0.34929(15) 0.7984(3) 0.66064(12) 0.0497(6) Uani 1 1 d . . . . .
H24A H 0.341567 0.701903 0.624758 0.075 Uiso 1 1 calc R U . . .
H24B H 0.398444 0.885699 0.660856 0.075 Uiso 1 1 calc R U . . .
H24C H 0.297838 0.881794 0.655386 0.075 Uiso 1 1 calc R U . . .
C25 C 0.43899(13) 0.1689(3) 0.54420(9) 0.0373(5) Uani 1 1 d . . . . .
H25A H 0.393714 0.230834 0.510557 0.056 Uiso 1 1 calc R U . . .
H25B H 0.418006 0.042148 0.558668 0.056 Uiso 1 1 calc R U . . .
H25C H 0.488519 0.140291 0.526739 0.056 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 C7 1.242(3) . ?
N1 N2 1.320(2) . ?
N1 C8 1.345(2) . ?
N1 C25 1.461(2) . ?
C1 C6 1.385(3) . ?
C1 C2 1.395(4) . ?
C1 H1 0.9500 . ?
O2 C7 1.239(3) . ?
N2 N3 1.328(2) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
N3 C9 1.375(2) . ?
N3 C16 1.454(2) . ?
C3 C4 1.368(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.519(3) . ?
C8 C9 1.369(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.468(3) . ?
C10 C15 1.394(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 C21 1.391(3) . ?
C17 C18 1.401(3) . ?
C17 C22 1.504(3) . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(3) . ?
C19 C23 1.512(3) . ?
C20 C21 1.394(3) . ?
C20 H20 0.9500 . ?
C21 C24 1.506(3) . ?
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 C8 113.02(15) . . ?
N2 N1 C25 119.07(15) . . ?
C8 N1 C25 127.89(16) . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
N1 N2 N3 104.01(14) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
N2 N3 C9 112.36(14) . . ?
N2 N3 C16 118.00(14) . . ?
C9 N3 C16 129.06(15) . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 120.1(2) . . ?
C1 C6 C7 120.0(2) . . ?
O2 C7 O1 125.5(2) . . ?
O2 C7 C6 117.21(19) . . ?
O1 C7 C6 117.26(19) . . ?
N1 C8 C9 106.21(16) . . ?
N1 C8 H8 126.9 . . ?
C9 C8 H8 126.9 . . ?
C8 C9 N3 104.39(16) . . ?
C8 C9 C10 130.34(16) . . ?
N3 C9 C10 125.27(16) . . ?
C15 C10 C11 119.07(18) . . ?
C15 C10 C9 122.52(16) . . ?
C11 C10 C9 118.36(17) . . ?
C12 C11 C10 120.44(19) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.09(19) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.82(19) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.50(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.09(18) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C17 C16 C21 124.06(17) . . ?
C17 C16 N3 119.40(16) . . ?
C21 C16 N3 116.53(16) . . ?
C16 C17 C18 116.54(18) . . ?
C16 C17 C22 121.97(17) . . ?
C18 C17 C22 121.48(18) . . ?
C19 C18 C17 121.64(19) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 118.87(18) . . ?
C20 C19 C23 120.3(2) . . ?
C18 C19 C23 120.8(2) . . ?
C19 C20 C21 122.13(19) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C16 C21 C20 116.60(19) . . ?
C16 C21 C24 121.82(18) . . ?
C20 C21 C24 121.58(19) . . ?
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
C8 N1 N2 N3 -0.13(19) . . . . ?
C25 N1 N2 N3 -178.58(15) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
N1 N2 N3 C9 0.06(19) . . . . ?
N1 N2 N3 C16 172.09(15) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 -177.0(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 177.3(2) . . . . ?
C5 C6 C7 O2 169.8(2) . . . . ?
C1 C6 C7 O2 -7.2(3) . . . . ?
C5 C6 C7 O1 -8.8(3) . . . . ?
C1 C6 C7 O1 174.2(2) . . . . ?
N2 N1 C8 C9 0.2(2) . . . . ?
C25 N1 C8 C9 178.44(18) . . . . ?
N1 C8 C9 N3 -0.11(19) . . . . ?
N1 C8 C9 C10 -179.64(17) . . . . ?
N2 N3 C9 C8 0.0(2) . . . . ?
C16 N3 C9 C8 -170.90(17) . . . . ?
N2 N3 C9 C10 179.59(16) . . . . ?
C16 N3 C9 C10 8.7(3) . . . . ?
C8 C9 C10 C15 -142.4(2) . . . . ?
N3 C9 C10 C15 38.1(3) . . . . ?
C8 C9 C10 C11 34.9(3) . . . . ?
N3 C9 C10 C11 -144.55(18) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C12 -177.25(18) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C9 C10 C15 C14 177.39(17) . . . . ?
N2 N3 C16 C17 81.7(2) . . . . ?
C9 N3 C16 C17 -107.8(2) . . . . ?
N2 N3 C16 C21 -97.31(19) . . . . ?
C9 N3 C16 C21 73.2(2) . . . . ?
C21 C16 C17 C18 -3.3(3) . . . . ?
N3 C16 C17 C18 177.77(16) . . . . ?
C21 C16 C17 C22 177.50(18) . . . . ?
N3 C16 C17 C22 -1.4(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C22 C17 C18 C19 178.87(18) . . . . ?
C17 C18 C19 C20 3.2(3) . . . . ?
C17 C18 C19 C23 -175.62(19) . . . . ?
C18 C19 C20 C21 -2.6(3) . . . . ?
C23 C19 C20 C21 176.18(19) . . . . ?
C17 C16 C21 C20 3.8(3) . . . . ?
N3 C16 C21 C20 -177.21(16) . . . . ?
C17 C16 C21 C24 -176.58(19) . . . . ?
N3 C16 C21 C24 2.4(3) . . . . ?
C19 C20 C21 C16 -0.7(3) . . . . ?
C19 C20 C21 C24 179.68(19) . . . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_wl520a
_database_code_depnum_ccdc_archive 'CCDC 2104506'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-22 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 H21 N3 O'
_chemical_formula_weight         367.44

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.077(7)
_cell_length_b                   8.652(3)
_cell_length_c                   23.320(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3849(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    122528
_cell_measurement_theta_min      3.120
_cell_measurement_theta_max      27.876

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             1552
_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    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6690
_exptl_absorpt_correction_T_max  0.7193
_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            122528
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.1451
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4477
_reflns_number_gt                3104
_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)+(0.0546P)²+2.2425P] 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       0.0107(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4477
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1303
_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
O1 O 0.12706(8) 0.25912(17) 0.04959(6) 0.0348(4) Uani 1 1 d . . . . .
N1 N 0.00157(9) 0.3213(2) 0.15700(7) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.13652(10) 0.1843(2) 0.20146(9) 0.0281(5) Uani 1 1 d . . . . .
H1 H 0.108771 0.267265 0.215450 0.034 Uiso 1 1 calc R U . . .
N2 N -0.04311(9) 0.43311(19) 0.16336(7) 0.0265(4) Uani 1 1 d . . . . .
C2 C 0.17323(11) 0.0920(3) 0.23937(9) 0.0318(5) Uani 1 1 d . . . . .
H2 H 0.171112 0.112646 0.279344 0.038 Uiso 1 1 calc R U . . .
N3 N -0.02292(8) 0.55059(18) 0.12816(7) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.21290(11) -0.0299(3) 0.21947(9) 0.0321(5) Uani 1 1 d . . . . .
H3 H 0.238125 -0.092868 0.245695 0.039 Uiso 1 1 calc R U . . .
C4 C 0.21599(11) -0.0605(3) 0.16117(10) 0.0325(5) Uani 1 1 d . . . . .
H4 H 0.242812 -0.145359 0.147493 0.039 Uiso 1 1 calc R U . . .
C5 C 0.18015(10) 0.0321(2) 0.12302(9) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.182781 0.011410 0.083075 0.032 Uiso 1 1 calc R U . . .
C6 C 0.14018(10) 0.1556(2) 0.14263(8) 0.0230(4) Uani 1 1 d . . . . .
C7 C 0.10713(10) 0.2588(2) 0.09940(9) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.05076(10) 0.3650(2) 0.11767(8) 0.0232(4) Uani 1 1 d . . . . .
C9 C 0.03578(10) 0.5123(2) 0.09864(8) 0.0216(4) Uani 1 1 d . . . . .
C10 C 0.07209(10) 0.6174(2) 0.05911(8) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.14487(10) 0.6264(2) 0.06101(8) 0.0256(4) Uani 1 1 d . . . . .
H11 H 0.170237 0.564031 0.087344 0.031 Uiso 1 1 calc R U . . .
C12 C 0.18044(11) 0.7254(2) 0.02486(9) 0.0289(5) Uani 1 1 d . . . . .
H12 H 0.230175 0.730112 0.026022 0.035 Uiso 1 1 calc R U . . .
C13 C 0.14381(12) 0.8176(3) -0.01296(9) 0.0333(5) Uani 1 1 d . . . . .
H13 H 0.168345 0.886817 -0.037405 0.040 Uiso 1 1 calc R U . . .
C14 C 0.07167(12) 0.8097(3) -0.01538(9) 0.0333(5) Uani 1 1 d . . . . .
H14 H 0.046671 0.872843 -0.041684 0.040 Uiso 1 1 calc R U . . .
C15 C 0.03563(11) 0.7099(2) 0.02035(8) 0.0281(5) Uani 1 1 d . . . . .
H15 H -0.014053 0.704514 0.018476 0.034 Uiso 1 1 calc R U . . .
C16 C -0.05771(10) 0.6975(2) 0.13453(8) 0.0210(4) Uani 1 1 d . . . . .
C17 C -0.02496(10) 0.8103(2) 0.16772(8) 0.0234(4) Uani 1 1 d . . . . .
C18 C -0.06090(10) 0.9476(2) 0.17648(8) 0.0254(4) Uani 1 1 d . . . . .
H18 H -0.039316 1.027355 0.198200 0.030 Uiso 1 1 calc R U . . .
C19 C -0.12753(11) 0.9715(2) 0.15438(8) 0.0256(4) Uani 1 1 d . . . . .
C20 C -0.15790(10) 0.8554(2) 0.12177(8) 0.0245(4) Uani 1 1 d . . . . .
H20 H -0.203416 0.871441 0.106360 0.029 Uiso 1 1 calc R U . . .
C21 C -0.12395(10) 0.7161(2) 0.11086(8) 0.0221(4) Uani 1 1 d . . . . .
C22 C 0.04560(11) 0.7833(3) 0.19429(9) 0.0302(5) Uani 1 1 d . . . . .
H22A H 0.081831 0.788651 0.164568 0.045 Uiso 1 1 calc R U . . .
H22B H 0.046510 0.681043 0.212321 0.045 Uiso 1 1 calc R U . . .
H22C H 0.054560 0.862731 0.223356 0.045 Uiso 1 1 calc R U . . .
C23 C -0.16513(12) 1.1206(2) 0.16651(10) 0.0339(5) Uani 1 1 d . . . . .
H23A H -0.140830 1.205813 0.147228 0.051 Uiso 1 1 calc R U . . .
H23B H -0.165712 1.139393 0.207954 0.051 Uiso 1 1 calc R U . . .
H23C H -0.213363 1.113897 0.152274 0.051 Uiso 1 1 calc R U . . .
C24 C -0.15768(11) 0.5896(2) 0.07642(9) 0.0285(5) Uani 1 1 d . . . . .
H24A H -0.200687 0.628670 0.058611 0.043 Uiso 1 1 calc R U . . .
H24B H -0.169121 0.502636 0.101690 0.043 Uiso 1 1 calc R U . . .
H24C H -0.125216 0.554805 0.046512 0.043 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 C7 1.222(2) . ?
N1 N2 1.298(2) . ?
N1 C8 1.365(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.396(3) . ?
N2 N3 1.362(2) . ?
C2 C3 1.379(3) . ?
N3 C9 1.356(2) . ?
N3 C16 1.442(2) . ?
C3 C4 1.386(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.487(3) . ?
C7 C8 1.477(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.469(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.382(3) . ?
C16 C21 1.388(3) . ?
C16 C17 1.393(3) . ?
C17 C18 1.387(3) . ?
C17 C22 1.500(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.387(3) . ?
C19 C23 1.503(3) . ?
C20 C21 1.391(3) . ?
C21 C24 1.503(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 108.77(16) . . ?
C2 C1 C6 120.07(19) . . ?
N1 N2 N3 107.57(15) . . ?
C3 C2 C1 120.3(2) . . ?
C9 N3 N2 110.91(15) . . ?
C9 N3 C16 130.41(16) . . ?
N2 N3 C16 117.76(14) . . ?
C2 C3 C4 120.0(2) . . ?
C5 C4 C3 120.0(2) . . ?
C4 C5 C6 120.44(19) . . ?
C5 C6 C1 119.15(18) . . ?
C5 C6 C7 118.11(18) . . ?
C1 C6 C7 122.59(18) . . ?
O1 C7 C8 119.96(18) . . ?
O1 C7 C6 120.91(18) . . ?
C8 C7 C6 119.11(17) . . ?
N1 C8 C9 109.23(17) . . ?
N1 C8 C7 121.48(17) . . ?
C9 C8 C7 129.22(18) . . ?
N3 C9 C8 103.52(16) . . ?
N3 C9 C10 123.83(17) . . ?
C8 C9 C10 132.57(18) . . ?
C11 C10 C15 119.12(18) . . ?
C11 C10 C9 119.04(17) . . ?
C15 C10 C9 121.84(18) . . ?
C12 C11 C10 120.39(19) . . ?
C13 C12 C11 120.03(19) . . ?
C12 C13 C14 120.20(19) . . ?
C13 C14 C15 120.2(2) . . ?
C14 C15 C10 120.09(19) . . ?
C21 C16 C17 123.22(18) . . ?
C21 C16 N3 118.71(17) . . ?
C17 C16 N3 117.91(17) . . ?
C18 C17 C16 117.39(18) . . ?
C18 C17 C22 121.05(18) . . ?
C16 C17 C22 121.55(18) . . ?
C17 C18 C19 121.75(19) . . ?
C20 C19 C18 118.57(18) . . ?
C20 C19 C23 121.72(19) . . ?
C18 C19 C23 119.71(19) . . ?
C19 C20 C21 122.22(18) . . ?
C16 C21 C20 116.83(18) . . ?
C16 C21 C24 121.18(17) . . ?
C20 C21 C24 121.97(18) . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.067

