# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_11675
_database_code_depnum_ccdc_archive 'CCDC 2085222'
loop_
_audit_author_name
_audit_author_address
'Yufeng Wang'
;Changcheng Road ,Qingdao, 
China
;
_audit_update_record             
;
2021-05-22 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N3'
_chemical_formula_weight         325.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6563(6)
_cell_length_b                   9.6499(4)
_cell_length_c                   14.6371(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.392(5)
_cell_angle_gamma                90
_cell_volume                     1731.55(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2093
_cell_measurement_theta_min      3.6230
_cell_measurement_theta_max      70.6830

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.580
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_T_min  0.59801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5821
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.140
_diffrn_reflns_theta_max         67.219
_diffrn_reflns_theta_full        67.219
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3076
_reflns_number_gt                2309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0658P)²+0.2027P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0097(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3076
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.50467(14) 1.08117(16) 0.62613(12) 0.0534(4) Uani 1 1 d . . . . .
N2 N 0.62930(18) 0.5160(2) 0.59236(16) 0.0766(6) Uani 1 1 d . . . . .
N3 N 0.37428(16) 0.5305(2) 0.73362(15) 0.0732(6) Uani 1 1 d . . . . .
C1 C 0.62444(15) 0.88570(19) 0.66880(12) 0.0450(4) Uani 1 1 d . . . . .
C2 C 0.72937(15) 0.8301(2) 0.68172(14) 0.0529(5) Uani 1 1 d . . . . .
H2 H 0.742643 0.740051 0.704232 0.064 Uiso 1 1 calc R U . . .
C3 C 0.81296(17) 0.9052(3) 0.66202(15) 0.0611(6) Uani 1 1 d . . . . .
H3 H 0.882153 0.866654 0.671081 0.073 Uiso 1 1 calc R U . . .
C4 C 0.79264(17) 1.0403(3) 0.62813(14) 0.0620(6) Uani 1 1 d . . . . .
H4 H 0.848623 1.090799 0.613151 0.074 Uiso 1 1 calc R U . . .
C5 C 0.69207(17) 1.1000(2) 0.61650(14) 0.0559(5) Uani 1 1 d . . . . .
H5 H 0.681058 1.190785 0.594937 0.067 Uiso 1 1 calc R U . . .
C6 C 0.60498(16) 1.02517(19) 0.63689(12) 0.0468(5) Uani 1 1 d . . . . .
C7 C 0.47322(19) 1.2212(2) 0.59405(17) 0.0632(6) Uani 1 1 d . . . . .
H7A H 0.490948 1.239901 0.534465 0.076 Uiso 1 1 calc R U . . .
H7B H 0.509618 1.288971 0.640185 0.076 Uiso 1 1 calc R U . . .
C8 C 0.35094(19) 1.2244(2) 0.58285(18) 0.0673(6) Uani 1 1 d . . . . .
H8A H 0.312161 1.203307 0.518454 0.081 Uiso 1 1 calc R U . . .
H8B H 0.327677 1.314511 0.599845 0.081 Uiso 1 1 calc R U . . .
C9 C 0.33120(19) 1.1130(2) 0.65037(17) 0.0657(6) Uani 1 1 d . . . . .
H9A H 0.345368 1.147816 0.714434 0.079 Uiso 1 1 calc R U . . .
H9B H 0.256989 1.078373 0.631509 0.079 Uiso 1 1 calc R U . . .
C10 C 0.41277(16) 1.0013(2) 0.64154(14) 0.0497(5) Uani 1 1 d . . . . .
H10 H 0.381791 0.947862 0.584184 0.060 Uiso 1 1 calc R U . . .
C11 C 0.45183(15) 0.89863(18) 0.72315(13) 0.0459(5) Uani 1 1 d . . . . .
H11 H 0.390298 0.840236 0.728494 0.055 Uiso 1 1 calc R U . . .
C12 C 0.49894(18) 0.9708(2) 0.81837(13) 0.0571(5) Uani 1 1 d . . . . .
H12A H 0.562056 1.024616 0.813574 0.069 Uiso 1 1 calc R U . . .
H12B H 0.444828 1.034976 0.830092 0.069 Uiso 1 1 calc R U . . .
C13 C 0.53240(15) 0.87479(19) 0.90188(13) 0.0460(5) Uani 1 1 d . . . . .
C14 C 0.63595(18) 0.8795(3) 0.96117(17) 0.0681(6) Uani 1 1 d . . . . .
H14 H 0.687764 0.939743 0.948287 0.082 Uiso 1 1 calc R U . . .
C15 C 0.6629(2) 0.7937(4) 1.0406(2) 0.0921(10) Uani 1 1 d . . . . .
H15 H 0.732376 0.798089 1.080923 0.110 Uiso 1 1 calc R U . . .
C16 C 0.5885(3) 0.7041(3) 1.0593(2) 0.0954(10) Uani 1 1 d . . . . .
H16 H 0.606959 0.646979 1.112031 0.115 Uiso 1 1 calc R U . . .
C17 C 0.4883(3) 0.6980(3) 1.0016(2) 0.0894(9) Uani 1 1 d . . . . .
H17 H 0.437641 0.635573 1.014027 0.107 Uiso 1 1 calc R U . . .
C18 C 0.45952(19) 0.7832(2) 0.92412(16) 0.0666(6) Uani 1 1 d . . . . .
H18 H 0.388967 0.778769 0.885796 0.080 Uiso 1 1 calc R U . . .
C19 C 0.53520(15) 0.80970(19) 0.69239(12) 0.0434(4) Uani 1 1 d . . . . .
C20 C 0.52240(15) 0.67010(19) 0.68141(13) 0.0457(5) Uani 1 1 d . . . . .
C21 C 0.58510(17) 0.58588(19) 0.63329(15) 0.0528(5) Uani 1 1 d . . . . .
C22 C 0.43942(17) 0.59502(19) 0.71121(15) 0.0522(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.353(2) . ?
N1 C7 1.453(2) . ?
N1 C10 1.459(2) . ?
N2 C21 1.137(3) . ?
N3 C22 1.144(2) . ?
C1 C2 1.401(3) . ?
C1 C6 1.426(3) . ?
C1 C19 1.458(2) . ?
C2 C3 1.371(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.369(3) . ?
C5 C6 1.410(3) . ?
C7 C8 1.515(3) . ?
C8 C9 1.523(3) . ?
C9 C10 1.520(3) . ?
C10 C11 1.536(3) . ?
C11 C19 1.513(2) . ?
C11 C12 1.539(3) . ?
C12 C13 1.508(3) . ?
C13 C18 1.374(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.399(4) . ?
C15 C16 1.355(4) . ?
C16 C17 1.339(4) . ?
C17 C18 1.374(3) . ?
C19 C20 1.362(3) . ?
C20 C22 1.430(3) . ?
C20 C21 1.437(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
C6 N1 C7 125.66(17) . . ?
C6 N1 C10 122.14(16) . . ?
C7 N1 C10 112.12(16) . . ?
C2 C1 C6 119.10(17) . . ?
C2 C1 C19 122.66(17) . . ?
C6 C1 C19 118.12(17) . . ?
C3 C2 C1 121.7(2) . . ?
C2 C3 C4 119.0(2) . . ?
C5 C4 C3 121.39(19) . . ?
C4 C5 C6 120.6(2) . . ?
N1 C6 C5 122.08(18) . . ?
N1 C6 C1 119.74(16) . . ?
C5 C6 C1 118.17(18) . . ?
N1 C7 C8 104.13(17) . . ?
C7 C8 C9 104.09(18) . . ?
C10 C9 C8 102.77(17) . . ?
N1 C10 C9 102.87(16) . . ?
N1 C10 C11 110.26(16) . . ?
C9 C10 C11 119.02(16) . . ?
C19 C11 C10 104.35(14) . . ?
C19 C11 C12 112.59(16) . . ?
C10 C11 C12 112.96(16) . . ?
C13 C12 C11 115.07(17) . . ?
C18 C13 C14 117.4(2) . . ?
C18 C13 C12 121.16(19) . . ?
C14 C13 C12 121.37(19) . . ?
C13 C14 C15 120.0(2) . . ?
C16 C15 C14 120.5(3) . . ?
C17 C16 C15 119.8(3) . . ?
C16 C17 C18 120.6(3) . . ?
C13 C18 C17 121.7(2) . . ?
C20 C19 C1 123.10(17) . . ?
C20 C19 C11 121.67(16) . . ?
C1 C19 C11 115.07(16) . . ?
C19 C20 C22 122.68(17) . . ?
C19 C20 C21 123.61(17) . . ?
C22 C20 C21 113.57(16) . . ?
N2 C21 C20 176.1(2) . . ?
N3 C22 C20 177.4(2) . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047

