# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Z-617
_database_code_depnum_ccdc_archive 'CCDC 2144481'
loop_
_audit_author_name
_audit_author_address
'Dinara Nasyrova'
;Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2022-09-15 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         'C16 H19 N3 O'
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34

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                   5.1190(5)
_cell_length_b                   11.5332(11)
_cell_length_c                   11.6739(11)
_cell_angle_alpha                100.610(3)
_cell_angle_beta                 92.588(3)
_cell_angle_gamma                94.229(3)
_cell_volume                     674.37(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7216
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      32.62

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            25877
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3942
_reflns_number_gt                2784
_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       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²+0.4225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3942
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1618
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.8388(3) 0.59619(11) 0.94323(11) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.5576(3) 0.20338(12) 0.88235(12) 0.0206(3) Uani 1 1 d . . . . .
N2 N 0.3759(3) 0.11651(13) 0.82657(13) 0.0219(3) Uani 1 1 d . . . . .
N3 N 0.7256(3) 0.40117(13) 0.88580(13) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.859(5) 0.391(2) 0.933(2) 0.039(7) Uiso 1 1 d . . . . .
C1 C 0.2547(3) 0.16500(15) 0.74580(15) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.3594(3) 0.28214(15) 0.74599(14) 0.0199(3) Uani 1 1 d . . . . .
C3 C 0.2751(3) 0.36146(14) 0.66477(14) 0.0194(3) Uani 1 1 d . . . . .
H3A H 0.091660 0.380010 0.682281 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4445(3) 0.47924(15) 0.68574(15) 0.0209(3) Uani 1 1 d . . . . .
H4A H 0.373107 0.530872 0.635076 0.025 Uiso 1 1 calc R U . . .
H4B H 0.624866 0.464277 0.663234 0.025 Uiso 1 1 calc R U . . .
C5 C 0.4557(3) 0.54400(15) 0.81335(15) 0.0217(3) Uani 1 1 d . . . . .
H5A H 0.465113 0.630349 0.815045 0.026 Uiso 1 1 calc R U . . .
H5B H 0.291191 0.521954 0.848521 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6850(3) 0.51695(15) 0.88666(14) 0.0200(3) Uani 1 1 d . . . . .
C7 C 0.5542(3) 0.30275(15) 0.83576(14) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.0315(4) 0.09569(16) 0.66958(16) 0.0256(4) Uani 1 1 d . . . . .
H8A H 0.020432 0.013435 0.681034 0.038 Uiso 1 1 calc R U . . .
H8B H 0.061055 0.097809 0.587611 0.038 Uiso 1 1 calc R U . . .
H8C H -0.132894 0.130508 0.690293 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2700(3) 0.30374(14) 0.53651(14) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.4496(4) 0.22436(16) 0.49299(15) 0.0243(4) Uani 1 1 d . . . . .
H10 H 0.582733 0.205660 0.544340 0.029 Uiso 1 1 calc R U . . .
C11 C 0.4371(3) 0.17196(16) 0.37525(15) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.559961 0.116971 0.347842 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2478(3) 0.19870(15) 0.29706(15) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.0727(4) 0.28068(16) 0.33987(15) 0.0242(4) Uani 1 1 d . . . . .
H13 H -0.055272 0.302046 0.287790 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0824(3) 0.33180(15) 0.45782(15) 0.0218(3) Uani 1 1 d . . . . .
H14 H -0.040647 0.386697 0.485191 0.026 Uiso 1 1 calc R U . . .
C15 C 0.2275(4) 0.13714(16) 0.17091(15) 0.0253(4) Uani 1 1 d . . . . .
H15A H 0.374098 0.087467 0.155897 0.038 Uiso 1 1 calc R U . . .
H15B H 0.233873 0.196384 0.120515 0.038 Uiso 1 1 calc R U . . .
H15C H 0.061348 0.087571 0.154323 0.038 Uiso 1 1 calc R U . . .
C16 C 0.7440(4) 0.17761(16) 0.97016(15) 0.0227(4) Uani 1 1 d . . . . .
H16A H 0.680179 0.105012 0.996017 0.034 Uiso 1 1 calc R U . . .
H16B H 0.762730 0.243551 1.036994 0.034 Uiso 1 1 calc R U . . .
H16C H 0.914594 0.166893 0.936624 0.034 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 C6 1.231(2) . ?
N1 C7 1.357(2) . ?
N1 N2 1.3639(19) . ?
N1 C16 1.454(2) . ?
N2 C1 1.334(2) . ?
N3 C6 1.365(2) . ?
N3 C7 1.401(2) . ?
N3 H3 0.89(3) . ?
C1 C2 1.416(2) . ?
C1 C8 1.499(2) . ?
C2 C7 1.388(2) . ?
C2 C3 1.504(2) . ?
C3 C9 1.521(2) . ?
C3 C4 1.530(2) . ?
C3 H3A 1.0000 . ?
C4 C5 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.507(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.392(2) . ?
C9 C14 1.395(2) . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(3) . ?
C12 C15 1.508(2) . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 111.78(13) . . ?
C7 N1 C16 128.10(14) . . ?
N2 N1 C16 119.69(14) . . ?
C1 N2 N1 104.59(14) . . ?
C6 N3 C7 126.22(15) . . ?
C6 N3 H3 113.8(16) . . ?
C7 N3 H3 118.9(16) . . ?
N2 C1 C2 112.35(15) . . ?
N2 C1 C8 119.69(15) . . ?
C2 C1 C8 127.95(15) . . ?
C7 C2 C1 103.61(15) . . ?
C7 C2 C3 129.84(15) . . ?
C1 C2 C3 126.54(14) . . ?
C2 C3 C9 113.40(14) . . ?
C2 C3 C4 111.91(13) . . ?
C9 C3 C4 109.71(14) . . ?
C2 C3 H3A 107.2 . . ?
C9 C3 H3A 107.2 . . ?
C4 C3 H3A 107.2 . . ?
C3 C4 C5 112.79(14) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 113.78(14) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
O1 C6 N3 120.06(16) . . ?
O1 C6 C5 121.60(15) . . ?
N3 C6 C5 118.29(14) . . ?
N1 C7 C2 107.64(14) . . ?
N1 C7 N3 118.52(14) . . ?
C2 C7 N3 133.78(16) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 117.87(15) . . ?
C10 C9 C3 122.47(14) . . ?
C14 C9 C3 119.65(15) . . ?
C9 C10 C11 120.94(16) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 121.17(16) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 117.93(15) . . ?
C11 C12 C15 120.77(16) . . ?
C13 C12 C15 121.26(15) . . ?
C14 C13 C12 120.97(16) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 121.07(16) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C1 -1.41(19) . . . . ?
C16 N1 N2 C1 -174.46(15) . . . . ?
N1 N2 C1 C2 1.44(19) . . . . ?
N1 N2 C1 C8 -177.51(15) . . . . ?
N2 C1 C2 C7 -1.0(2) . . . . ?
C8 C1 C2 C7 177.89(17) . . . . ?
N2 C1 C2 C3 178.21(16) . . . . ?
C8 C1 C2 C3 -3.0(3) . . . . ?
C7 C2 C3 C9 127.42(19) . . . . ?
C1 C2 C3 C9 -51.5(2) . . . . ?
C7 C2 C3 C4 2.7(3) . . . . ?
C1 C2 C3 C4 -176.27(16) . . . . ?
C2 C3 C4 C5 -54.14(19) . . . . ?
C9 C3 C4 C5 179.08(14) . . . . ?
C3 C4 C5 C6 92.94(18) . . . . ?
C7 N3 C6 O1 172.97(16) . . . . ?
C7 N3 C6 C5 -9.4(3) . . . . ?
C4 C5 C6 O1 126.14(18) . . . . ?
C4 C5 C6 N3 -51.4(2) . . . . ?
N2 N1 C7 C2 0.9(2) . . . . ?
C16 N1 C7 C2 173.18(16) . . . . ?
N2 N1 C7 N3 178.38(14) . . . . ?
C16 N1 C7 N3 -9.3(3) . . . . ?
C1 C2 C7 N1 0.04(19) . . . . ?
C3 C2 C7 N1 -179.08(17) . . . . ?
C1 C2 C7 N3 -176.95(19) . . . . ?
C3 C2 C7 N3 3.9(3) . . . . ?
C6 N3 C7 N1 -151.34(17) . . . . ?
C6 N3 C7 C2 25.4(3) . . . . ?
C2 C3 C9 C10 -34.6(2) . . . . ?
C4 C3 C9 C10 91.37(19) . . . . ?
C2 C3 C9 C14 146.55(16) . . . . ?
C4 C3 C9 C14 -87.52(18) . . . . ?
C14 C9 C10 C11 -1.9(3) . . . . ?
C3 C9 C10 C11 179.15(16) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C10 C11 C12 C15 -177.04(17) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
C15 C12 C13 C14 176.05(16) . . . . ?
C12 C13 C14 C9 0.9(3) . . . . ?
C10 C9 C14 C13 1.0(3) . . . . ?
C3 C9 C14 C13 179.91(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O1 0.89(3) 2.04(3) 2.9194(19) 168(2) 2_767 yes

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.063



