# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_AI-342
_database_code_depnum_ccdc_archive 'CCDC 2026499'
loop_
_audit_author_name
_audit_author_address
'Tatyana Volkhina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2020-10-21 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2020-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N3 O, C2 H3 N'
_chemical_formula_sum            'C22 H24 N4 O'
_chemical_formula_weight         360.45
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9795(8)
_cell_length_b                   9.9569(11)
_cell_length_c                   14.5673(17)
_cell_angle_alpha                108.531(2)
_cell_angle_beta                 92.161(3)
_cell_angle_gamma                97.846(3)
_cell_volume                     947.32(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1434
_cell_measurement_temperature    120
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0573 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.8933.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.184
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2838
_reflns_number_total             4568
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C2S(H2SA,H2SB,
 H2SC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.50549(18) 0.86762(13) 0.82538(10) 0.0232(3) Uani 1 1 d . . . . .
N1 N 0.6400(2) 0.76443(15) 0.92858(11) 0.0182(3) Uani 1 1 d . . . . .
N2 N 0.5590(2) 0.52639(16) 0.84750(11) 0.0191(3) Uani 1 1 d . . . . .
N3 N 0.1927(2) 0.40885(16) 0.72946(12) 0.0232(4) Uani 1 1 d . . . . .
C1 C 0.4691(2) 0.60418(19) 0.79054(13) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.2446(3) 0.56170(19) 0.78373(13) 0.0181(4) Uani 1 1 d . . . . .
H2 H 0.2083 0.5752 0.8515 0.022 Uiso 1 1 calc R . . . .
C3 C 0.2922(3) 0.34138(19) 0.65148(13) 0.0199(4) Uani 1 1 d . . . . .
C4 C 0.4643(3) 0.41385(19) 0.62946(13) 0.0203(4) Uani 1 1 d . . . . .
C5 C 0.5388(3) 0.56702(19) 0.68862(13) 0.0196(4) Uani 1 1 d . . . . .
H5A H 0.4934 0.6312 0.6556 0.024 Uiso 1 1 calc R . . . .
H5B H 0.6825 0.5829 0.6935 0.024 Uiso 1 1 calc R . . . .
C6 C 0.2290(3) 0.1971(2) 0.59428(15) 0.0268(5) Uani 1 1 d . . . . .
H6 H 0.1138 0.1465 0.6077 0.032 Uiso 1 1 calc R . . . .
C7 C 0.3328(3) 0.1284(2) 0.51885(15) 0.0326(5) Uani 1 1 d . . . . .
H7 H 0.2889 0.0308 0.4818 0.039 Uiso 1 1 calc R . . . .
C8 C 0.4997(3) 0.1999(2) 0.49668(15) 0.0337(5) Uani 1 1 d . . . . .
H8 H 0.5694 0.1528 0.4442 0.040 Uiso 1 1 calc R . . . .
C9 C 0.5628(3) 0.3415(2) 0.55266(14) 0.0264(5) Uani 1 1 d . . . . .
H9 H 0.6777 0.3908 0.5379 0.032 Uiso 1 1 calc R . . . .
C10 C 0.5337(2) 0.76270(19) 0.84687(13) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.6505(3) 0.62244(19) 0.92332(13) 0.0183(4) Uani 1 1 d . . . . .
C12 C 0.7344(3) 0.8950(2) 1.00330(14) 0.0245(4) Uani 1 1 d . . . . .
H12A H 0.6680 0.9083 1.0629 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.7283 0.9773 0.9808 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.8704 0.8872 1.0165 0.037 Uiso 1 1 calc GR . . . .
C13 C 0.7614(3) 0.5936(2) 1.00227(14) 0.0247(4) Uani 1 1 d . . . . .
H13A H 0.8947 0.6444 1.0109 0.037 Uiso 1 1 calc GR . . . .
H13B H 0.7631 0.4903 0.9851 0.037 Uiso 1 1 calc GR . . . .
H13C H 0.6994 0.6271 1.0629 0.037 Uiso 1 1 calc GR . . . .
C14 C 0.0012(3) 0.3417(2) 0.74230(16) 0.0305(5) Uani 1 1 d . . . . .
H14A H -0.0853 0.3221 0.6834 0.046 Uiso 1 1 calc GR . . . .
H14B H -0.0518 0.4063 0.7978 0.046 Uiso 1 1 calc GR . . . .
H14C H 0.0118 0.2515 0.7544 0.046 Uiso 1 1 calc GR . . . .
C15 C 0.1340(2) 0.65663(19) 0.74482(13) 0.0181(4) Uani 1 1 d . . . . .
C16 C 0.0966(3) 0.6312(2) 0.64583(14) 0.0225(4) Uani 1 1 d . . . . .
H16 H 0.1350 0.5496 0.6003 0.027 Uiso 1 1 calc R . . . .
C17 C 0.0034(3) 0.7242(2) 0.61277(15) 0.0264(5) Uani 1 1 d . . . . .
H17 H -0.0204 0.7065 0.5450 0.032 Uiso 1 1 calc R . . . .
C18 C -0.0548(3) 0.8424(2) 0.67872(15) 0.0270(5) Uani 1 1 d . . . . .
H18 H -0.1167 0.9067 0.6562 0.032 Uiso 1 1 calc R . . . .
C19 C -0.0227(3) 0.8672(2) 0.77759(15) 0.0254(5) Uani 1 1 d . . . . .
H19 H -0.0643 0.9476 0.8228 0.030 Uiso 1 1 calc R . . . .
C20 C 0.0704(3) 0.7743(2) 0.81038(14) 0.0215(4) Uani 1 1 d . . . . .
H20 H 0.0909 0.7911 0.8782 0.026 Uiso 1 1 calc R . . . .
N1S N 0.7619(3) 0.21012(19) 0.93179(14) 0.0352(5) Uani 1 1 d . . . . .
C1S C 0.6651(3) 0.1827(2) 0.86114(16) 0.0265(5) Uani 1 1 d . . . . .
C2S C 0.5406(3) 0.1512(2) 0.77192(15) 0.0334(5) Uani 1 1 d . . . . .
H2SA H 0.6149 0.1160 0.7158 0.050 Uiso 1 1 calc GR . . . .
H2SB H 0.4931 0.2386 0.7702 0.050 Uiso 1 1 calc GR . . . .
H2SC H 0.4301 0.0777 0.7698 0.050 Uiso 1 1 calc GR . . . .


_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 C10 1.220(2) . ?
N1 C10 1.373(2) . ?
N1 C11 1.404(2) . ?
N1 C12 1.456(2) . ?
N2 C1 1.478(2) . ?
N2 C11 1.285(2) . ?
N3 C2 1.461(2) . ?
N3 C3 1.388(2) . ?
N3 C14 1.457(2) . ?
C1 C2 1.558(2) . ?
C1 C5 1.527(2) . ?
C1 C10 1.524(2) . ?
C2 C15 1.522(2) . ?
C3 C4 1.416(3) . ?
C3 C6 1.411(3) . ?
C4 C5 1.501(2) . ?
C4 C9 1.387(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.386(3) . ?
C11 C13 1.486(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.395(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.384(3) . ?
C18 C19 1.386(3) . ?
C19 C20 1.388(3) . ?
N1S C1S 1.144(3) . ?
C1S C2S 1.457(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
C10 N1 C11 108.64(15) . . ?
C10 N1 C12 123.93(15) . . ?
C11 N1 C12 127.31(15) . . ?
C11 N2 C1 106.38(15) . . ?
C3 N3 C2 121.75(15) . . ?
C3 N3 C14 120.11(16) . . ?
C14 N3 C2 115.84(16) . . ?
N2 C1 C2 108.47(14) . . ?
N2 C1 C5 110.89(14) . . ?
N2 C1 C10 105.30(14) . . ?
C5 C1 C2 109.84(14) . . ?
C10 C1 C2 111.79(14) . . ?
C10 C1 C5 110.47(14) . . ?
N3 C2 C1 108.99(14) . . ?
N3 C2 C15 113.64(15) . . ?
C15 C2 C1 113.38(14) . . ?
N3 C3 C4 120.83(16) . . ?
N3 C3 C6 120.97(17) . . ?
C6 C3 C4 118.16(18) . . ?
C3 C4 C5 120.31(17) . . ?
C9 C4 C3 119.17(18) . . ?
C9 C4 C5 120.52(17) . . ?
C4 C5 C1 111.26(15) . . ?
C7 C6 C3 120.82(19) . . ?
C8 C7 C6 120.97(19) . . ?
C7 C8 C9 118.5(2) . . ?
C8 C9 C4 122.3(2) . . ?
O1 C10 N1 125.90(17) . . ?
O1 C10 C1 129.31(17) . . ?
N1 C10 C1 104.75(15) . . ?
N1 C11 C13 119.77(16) . . ?
N2 C11 N1 114.86(16) . . ?
N2 C11 C13 125.37(17) . . ?
C16 C15 C2 122.15(17) . . ?
C16 C15 C20 118.74(17) . . ?
C20 C15 C2 119.10(16) . . ?
C15 C16 C17 120.62(18) . . ?
C18 C17 C16 119.95(18) . . ?
C17 C18 C19 120.06(18) . . ?
C18 C19 C20 119.88(19) . . ?
C19 C20 C15 120.71(18) . . ?
N1S C1S C2S 178.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
