# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_exp_11691
_database_code_depnum_ccdc_archive 'CCDC 2077987'
loop_
_audit_author_name
_audit_author_address
wang
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-04-16 deposited with the CCDC.	2021-09-03 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            'C21 H23 N3'
_chemical_formula_weight         317.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   15.4459(6)
_cell_length_b                   7.45856(17)
_cell_length_c                   16.2431(6)
_cell_angle_alpha                90
_cell_angle_beta                 118.081(5)
_cell_angle_gamma                90
_cell_volume                     1650.99(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2659
_cell_measurement_theta_min      3.0880
_cell_measurement_theta_max      70.9460

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.587
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_T_min  0.85670
_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            5325
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.258
_diffrn_reflns_theta_max         67.215
_diffrn_reflns_theta_full        67.215
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2962
_reflns_number_gt                2546
_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)+(0.0611P)²+0.5453P] 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       0.0038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2962
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.11666(10) 0.45070(19) 0.23041(9) 0.0339(3) Uani 1 1 d . . . . .
N2 N -0.12169(10) 0.5608(2) 0.17384(10) 0.0398(4) Uani 1 1 d . . . . .
N3 N -0.02582(10) 0.83510(17) 0.31640(10) 0.0329(3) Uani 1 1 d . . . . .
C1 C 0.20542(12) 0.4406(2) 0.31058(11) 0.0324(4) Uani 1 1 d . . . . .
C2 C 0.28587(13) 0.3297(3) 0.33228(13) 0.0424(4) Uani 1 1 d . . . . .
H2 H 0.285279 0.244951 0.290018 0.051 Uiso 1 1 calc R U . . .
C3 C 0.36640(13) 0.3504(3) 0.41884(14) 0.0460(5) Uani 1 1 d . . . . .
H3 H 0.421223 0.278391 0.435030 0.055 Uiso 1 1 calc R U . . .
C4 C 0.36760(13) 0.4769(3) 0.48276(13) 0.0430(4) Uani 1 1 d . . . . .
H4 H 0.422780 0.486402 0.540864 0.052 Uiso 1 1 calc R U . . .
C5 C 0.28858(12) 0.5876(2) 0.46129(12) 0.0358(4) Uani 1 1 d . . . . .
H5 H 0.290152 0.671630 0.504259 0.043 Uiso 1 1 calc R U . . .
C6 C 0.20556(11) 0.5717(2) 0.37354(11) 0.0299(4) Uani 1 1 d . . . . .
C7 C 0.11384(11) 0.6631(2) 0.32763(11) 0.0302(4) Uani 1 1 d . . . . .
C8 C 0.08168(11) 0.8190(2) 0.36441(11) 0.0326(4) Uani 1 1 d . . . . .
H8 H 0.105355 0.804067 0.431565 0.039 Uiso 1 1 calc R U . . .
C9 C 0.11316(14) 1.0041(2) 0.34547(15) 0.0470(5) Uani 1 1 d . . . . .
H9A H 0.174565 1.041656 0.397739 0.056 Uiso 1 1 calc R U . . .
H9B H 0.121130 1.000802 0.289713 0.056 Uiso 1 1 calc R U . . .
C10 C 0.03050(17) 1.1299(3) 0.33254(19) 0.0617(6) Uani 1 1 d . . . . .
H10A H 0.053880 1.219701 0.381514 0.074 Uiso 1 1 calc R U . . .
H10B H 0.004600 1.190330 0.272733 0.074 Uiso 1 1 calc R U . . .
C11 C -0.04731(15) 1.0158(2) 0.33699(16) 0.0496(5) Uani 1 1 d . . . . .
H11A H -0.042986 1.020905 0.398486 0.059 Uiso 1 1 calc R U . . .
H11B H -0.112316 1.053969 0.291032 0.059 Uiso 1 1 calc R U . . .
C12 C -0.07809(11) 0.6878(2) 0.32968(12) 0.0321(4) Uani 1 1 d . . . . .
C13 C -0.08490(13) 0.6746(2) 0.41164(13) 0.0407(4) Uani 1 1 d . . . . .
H13 H -0.051060 0.757038 0.459034 0.049 Uiso 1 1 calc R U . . .
C14 C -0.13999(15) 0.5439(3) 0.42557(14) 0.0487(5) Uani 1 1 d . . . . .
H14 H -0.144333 0.539143 0.480722 0.058 Uiso 1 1 calc R U . . .
C15 C -0.18824(14) 0.4209(3) 0.35562(15) 0.0485(5) Uani 1 1 d . . . . .
H15 H -0.226719 0.332996 0.363021 0.058 Uiso 1 1 calc R U . . .
C16 C -0.18025(13) 0.4264(2) 0.27463(13) 0.0412(4) Uani 1 1 d . . . . .
H16 H -0.212526 0.340045 0.229022 0.049 Uiso 1 1 calc R U . . .
C17 C -0.12493(11) 0.5583(2) 0.25881(12) 0.0328(4) Uani 1 1 d . . . . .
C18 C -0.03841(12) 0.6398(2) 0.16629(11) 0.0361(4) Uani 1 1 d . . . . .
H18A H -0.044019 0.769305 0.166605 0.043 Uiso 1 1 calc R U . . .
H18B H -0.043722 0.605898 0.106428 0.043 Uiso 1 1 calc R U . . .
C19 C 0.06191(11) 0.5875(2) 0.24143(11) 0.0310(4) Uani 1 1 d . . . . .
C20 C 0.09084(15) 0.3424(3) 0.14814(13) 0.0498(5) Uani 1 1 d . . . . .
H20A H 0.107463 0.405722 0.106046 0.075 Uiso 1 1 calc R U . . .
H20B H 0.021636 0.318435 0.117861 0.075 Uiso 1 1 calc R U . . .
H20C H 0.126308 0.231289 0.165953 0.075 Uiso 1 1 calc R U . . .
C21 C -0.17652(16) 0.4261(3) 0.10517(15) 0.0605(6) Uani 1 1 d . . . . .
H21A H -0.149858 0.309849 0.128970 0.091 Uiso 1 1 calc R U . . .
H21B H -0.172184 0.448861 0.049052 0.091 Uiso 1 1 calc R U . . .
H21C H -0.244018 0.430109 0.091789 0.091 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 C1 1.379(2) . ?
N1 C19 1.389(2) . ?
N1 C20 1.448(2) . ?
N2 C17 1.405(2) . ?
N2 C21 1.443(2) . ?
N2 C18 1.472(2) . ?
N3 C12 1.439(2) . ?
N3 C11 1.464(2) . ?
N3 C8 1.470(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.376(3) . ?
C5 C6 1.403(2) . ?
C6 C7 1.426(2) . ?
C7 C19 1.365(2) . ?
C7 C8 1.495(2) . ?
C8 C9 1.542(2) . ?
C9 C10 1.518(3) . ?
C10 C11 1.502(3) . ?
C12 C13 1.387(2) . ?
C12 C17 1.413(2) . ?
C13 C14 1.381(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.379(3) . ?
C16 C17 1.404(2) . ?
C18 C19 1.504(2) . ?

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
C1 N1 C19 108.26(13) . . ?
C1 N1 C20 124.12(15) . . ?
C19 N1 C20 127.50(15) . . ?
C17 N2 C21 118.11(16) . . ?
C17 N2 C18 121.61(13) . . ?
C21 N2 C18 115.62(15) . . ?
C12 N3 C11 117.74(13) . . ?
C12 N3 C8 115.56(12) . . ?
C11 N3 C8 105.96(13) . . ?
N1 C1 C2 130.05(16) . . ?
N1 C1 C6 107.92(14) . . ?
C2 C1 C6 122.02(16) . . ?
C3 C2 C1 117.42(17) . . ?
C2 C3 C4 121.57(17) . . ?
C5 C4 C3 121.15(17) . . ?
C4 C5 C6 118.97(16) . . ?
C5 C6 C1 118.85(15) . . ?
C5 C6 C7 134.33(15) . . ?
C1 C6 C7 106.82(14) . . ?
C19 C7 C6 107.36(14) . . ?
C19 C7 C8 125.85(14) . . ?
C6 C7 C8 126.73(14) . . ?
N3 C8 C7 110.88(13) . . ?
N3 C8 C9 101.81(13) . . ?
C7 C8 C9 114.91(14) . . ?
C10 C9 C8 104.93(15) . . ?
C11 C10 C9 106.42(16) . . ?
N3 C11 C10 103.79(15) . . ?
C13 C12 C17 119.50(16) . . ?
C13 C12 N3 119.94(15) . . ?
C17 C12 N3 120.54(15) . . ?
C14 C13 C12 122.54(17) . . ?
C15 C14 C13 118.15(18) . . ?
C14 C15 C16 120.76(18) . . ?
C15 C16 C17 122.09(17) . . ?
C16 C17 N2 119.69(15) . . ?
C16 C17 C12 116.88(16) . . ?
N2 C17 C12 123.38(15) . . ?
N2 C18 C19 115.82(14) . . ?
C7 C19 N1 109.63(14) . . ?
C7 C19 C18 127.48(15) . . ?
N1 C19 C18 122.88(14) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037

