# 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_439
_database_code_depnum_ccdc_archive 'CCDC 2008292'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Ural Federal University, Institute of Organic Synthesis
Russia
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2021-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N5 O'
_chemical_formula_sum            'C20 H19 N5 O'
_chemical_formula_weight         345.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   6.7011(11)
_cell_length_b                   9.1071(11)
_cell_length_c                   28.951(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.176(10)
_cell_angle_gamma                90.00
_cell_volume                     1765.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1372
_cell_measurement_theta_min      3.5950
_cell_measurement_theta_max      21.7290

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.084

_exptl_absorpt_correction_T_min  0.33879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12762
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_av_sigmaI/netI    0.1030
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3599
_reflns_number_gt                1730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0075(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3599
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1986
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1578(4) 0.1042(3) 0.09517(9) 0.0480(7) Uani 1 1 d . . .
O1 O 0.2609(5) 0.3763(3) 0.05353(9) 0.0715(9) Uani 1 1 d . . .
C1 C 0.2933(5) 0.2075(3) 0.11377(10) 0.0446(8) Uani 1 1 d . . .
N2 N -0.0438(5) 0.1183(4) 0.10327(10) 0.0587(8) Uani 1 1 d . . .
C2 C 0.4167(5) 0.2041(4) 0.15593(10) 0.0436(8) Uani 1 1 d . . .
N3 N -0.1378(5) 0.0143(3) 0.08116(10) 0.0560(8) Uani 1 1 d . . .
C3 C 0.4845(5) 0.4150(3) 0.12062(10) 0.0398(8) Uani 1 1 d . . .
N4 N 0.3306(4) 0.3306(3) 0.09190(8) 0.0491(8) Uani 1 1 d . . .
C4 C -0.0004(5) -0.0714(4) 0.05848(11) 0.0446(8) Uani 1 1 d . . .
N5 N 0.5267(4) 0.3200(3) 0.16023(8) 0.0438(7) Uani 1 1 d . . .
C5 C -0.0299(7) -0.1930(4) 0.03045(11) 0.0522(10) Uani 1 1 d . . .
C6 C 0.1368(7) -0.2564(5) 0.01298(12) 0.0577(10) Uani 1 1 d . . .
C7 C 0.3273(6) -0.1972(4) 0.02221(12) 0.0587(10) Uani 1 1 d . . .
C8 C 0.3597(6) -0.0758(4) 0.04942(12) 0.0525(9) Uani 1 1 d . . .
C9 C 0.1895(5) -0.0139(4) 0.06765(10) 0.0426(8) Uani 1 1 d . . .
C10 C 0.4220(5) 0.0858(4) 0.19050(10) 0.0456(8) Uani 1 1 d . . .
C11 C 0.2516(6) 0.0091(4) 0.20133(11) 0.0571(10) Uani 1 1 d . . .
H11A H 0.1321 0.0282 0.1850 0.068 Uiso 1 1 calc R . .
C12 C 0.2562(7) -0.0954(4) 0.23601(13) 0.0705(12) Uani 1 1 d . . .
H12A H 0.1408 -0.1463 0.2429 0.085 Uiso 1 1 calc R . .
C13 C 0.4336(8) -0.1235(5) 0.26030(13) 0.0694(12) Uani 1 1 d . . .
H13A H 0.4375 -0.1921 0.2841 0.083 Uiso 1 1 calc R . .
C14 C 0.6037(7) -0.0501(4) 0.24930(12) 0.0660(12) Uani 1 1 d . . .
H14A H 0.7234 -0.0710 0.2652 0.079 Uiso 1 1 calc R . .
C15 C 0.5995(6) 0.0542(4) 0.21491(11) 0.0529(9) Uani 1 1 d . . .
H15A H 0.7160 0.1038 0.2080 0.064 Uiso 1 1 calc R . .
C16 C 0.3923(5) 0.5597(4) 0.13496(11) 0.0501(9) Uani 1 1 d . . .
H16A H 0.3397 0.6107 0.1077 0.060 Uiso 1 1 calc R . .
H16B H 0.2821 0.5404 0.1549 0.060 Uiso 1 1 calc R . .
C17 C 0.5449(7) 0.6563(4) 0.16024(12) 0.0621(11) Uani 1 1 d . . .
H17A H 0.5828 0.6117 0.1897 0.075 Uiso 1 1 calc R . .
H17B H 0.4857 0.7512 0.1663 0.075 Uiso 1 1 calc R . .
C18 C 0.7314(7) 0.6775(5) 0.13193(14) 0.0754(13) Uani 1 1 d . . .
H18A H 0.6966 0.7342 0.1044 0.090 Uiso 1 1 calc R . .
H18B H 0.8304 0.7325 0.1501 0.090 Uiso 1 1 calc R . .
C19 C 0.8188(6) 0.5337(5) 0.11809(13) 0.0647(11) Uani 1 1 d . . .
H19A H 0.8683 0.4822 0.1455 0.078 Uiso 1 1 calc R . .
H19B H 0.9309 0.5515 0.0986 0.078 Uiso 1 1 calc R . .
C20 C 0.6665(5) 0.4382(4) 0.09220(11) 0.0522(9) Uani 1 1 d . . .
H20A H 0.6270 0.4848 0.0631 0.063 Uiso 1 1 calc R . .
H20B H 0.7260 0.3440 0.0853 0.063 Uiso 1 1 calc R . .
H7 H 0.466(7) -0.246(4) 0.0114(12) 0.079(12) Uiso 1 1 d . . .
H8 H 0.488(7) -0.030(5) 0.0579(13) 0.089(14) Uiso 1 1 d . . .
H6 H 0.124(7) -0.347(5) -0.0054(14) 0.096(15) Uiso 1 1 d . . .
H5 H -0.139(7) -0.240(5) 0.0249(13) 0.097(16) Uiso 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 C9 1.360(4) . ?
N1 N2 1.386(4) . ?
N1 C1 1.401(4) . ?
O1 N4 1.259(3) . ?
C1 N4 1.316(4) . ?
C1 C2 1.448(4) . ?
N2 N3 1.293(4) . ?
C2 N5 1.291(4) . ?
C2 C10 1.470(4) . ?
N3 C4 1.390(5) . ?
C3 N5 1.456(4) . ?
C3 N4 1.510(4) . ?
C3 C20 1.512(5) . ?
C3 C16 1.519(5) . ?
C4 C5 1.383(5) . ?
C4 C9 1.392(5) . ?
C5 C6 1.371(6) . ?
C5 H5 0.86(5) . ?
C6 C7 1.402(5) . ?
C6 H6 0.98(5) . ?
C7 C8 1.370(5) . ?
C7 H7 1.09(4) . ?
C8 C9 1.394(5) . ?
C8 H8 0.98(5) . ?
C10 C11 1.385(5) . ?
C10 C15 1.391(5) . ?
C11 C12 1.383(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.369(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.516(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.533(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.495(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.517(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
C9 N1 N2 110.3(3) . . ?
C9 N1 C1 130.0(3) . . ?
N2 N1 C1 119.6(3) . . ?
N4 C1 N1 121.3(3) . . ?
N4 C1 C2 108.1(3) . . ?
N1 C1 C2 130.6(3) . . ?
N3 N2 N1 107.9(3) . . ?
N5 C2 C1 111.7(3) . . ?
N5 C2 C10 122.3(3) . . ?
C1 C2 C10 126.0(3) . . ?
N2 N3 C4 109.0(3) . . ?
N5 C3 N4 103.8(2) . . ?
N5 C3 C20 112.0(3) . . ?
N4 C3 C20 108.6(3) . . ?
N5 C3 C16 111.7(2) . . ?
N4 C3 C16 108.4(3) . . ?
C20 C3 C16 111.8(3) . . ?
O1 N4 C1 129.4(3) . . ?
O1 N4 C3 122.7(3) . . ?
C1 N4 C3 107.9(2) . . ?
C5 C4 N3 130.1(4) . . ?
C5 C4 C9 121.5(4) . . ?
N3 C4 C9 108.4(3) . . ?
C2 N5 C3 108.5(3) . . ?
C6 C5 C4 117.0(4) . . ?
C6 C5 H5 115(3) . . ?
C4 C5 H5 128(3) . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 120(3) . . ?
C7 C6 H6 119(3) . . ?
C8 C7 C6 122.9(4) . . ?
C8 C7 H7 112(2) . . ?
C6 C7 H7 125(2) . . ?
C7 C8 C9 115.5(4) . . ?
C7 C8 H8 127(3) . . ?
C9 C8 H8 117(3) . . ?
N1 C9 C4 104.3(3) . . ?
N1 C9 C8 133.6(3) . . ?
C4 C9 C8 122.1(3) . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C2 121.7(3) . . ?
C15 C10 C2 119.8(3) . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 119.5(4) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C14 C15 C10 120.3(4) . . ?
C14 C15 H15A 119.9 . . ?
C10 C15 H15A 119.9 . . ?
C17 C16 C3 111.2(3) . . ?
C17 C16 H16A 109.4 . . ?
C3 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C3 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.3(3) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 111.6(3) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 111.8(3) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C3 C20 C19 110.6(3) . . ?
C3 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?

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
C9 N1 C1 N4 91.9(4) . . . . ?
N2 N1 C1 N4 -86.1(4) . . . . ?
C9 N1 C1 C2 -86.2(5) . . . . ?
N2 N1 C1 C2 95.8(4) . . . . ?
C9 N1 N2 N3 -0.9(4) . . . . ?
C1 N1 N2 N3 177.4(3) . . . . ?
N4 C1 C2 N5 -0.1(4) . . . . ?
N1 C1 C2 N5 178.2(3) . . . . ?
N4 C1 C2 C10 -179.9(3) . . . . ?
N1 C1 C2 C10 -1.6(6) . . . . ?
N1 N2 N3 C4 0.7(4) . . . . ?
N1 C1 N4 O1 -0.5(6) . . . . ?
C2 C1 N4 O1 178.0(3) . . . . ?
N1 C1 N4 C3 -179.0(3) . . . . ?
C2 C1 N4 C3 -0.5(4) . . . . ?
N5 C3 N4 O1 -177.7(3) . . . . ?
C20 C3 N4 O1 -58.3(4) . . . . ?
C16 C3 N4 O1 63.4(4) . . . . ?
N5 C3 N4 C1 0.9(3) . . . . ?
C20 C3 N4 C1 120.3(3) . . . . ?
C16 C3 N4 C1 -118.0(3) . . . . ?
N2 N3 C4 C5 -179.4(3) . . . . ?
N2 N3 C4 C9 -0.2(4) . . . . ?
C1 C2 N5 C3 0.7(4) . . . . ?
C10 C2 N5 C3 -179.5(3) . . . . ?
N4 C3 N5 C2 -0.9(4) . . . . ?
C20 C3 N5 C2 -118.0(3) . . . . ?
C16 C3 N5 C2 115.7(3) . . . . ?
N3 C4 C5 C6 -179.4(3) . . . . ?
C9 C4 C5 C6 1.5(5) . . . . ?
C4 C5 C6 C7 -1.8(5) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
N2 N1 C9 C4 0.8(3) . . . . ?
C1 N1 C9 C4 -177.3(3) . . . . ?
N2 N1 C9 C8 179.9(3) . . . . ?
C1 N1 C9 C8 1.8(6) . . . . ?
C5 C4 C9 N1 178.9(3) . . . . ?
N3 C4 C9 N1 -0.4(3) . . . . ?
C5 C4 C9 C8 -0.3(5) . . . . ?
N3 C4 C9 C8 -179.6(3) . . . . ?
C7 C8 C9 N1 -179.4(3) . . . . ?
C7 C8 C9 C4 -0.4(5) . . . . ?
N5 C2 C10 C11 144.1(3) . . . . ?
C1 C2 C10 C11 -36.1(5) . . . . ?
N5 C2 C10 C15 -32.4(5) . . . . ?
C1 C2 C10 C15 147.3(3) . . . . ?
C15 C10 C11 C12 0.8(5) . . . . ?
C2 C10 C11 C12 -175.8(3) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C12 C13 C14 C15 1.5(6) . . . . ?
C13 C14 C15 C10 -0.5(6) . . . . ?
C11 C10 C15 C14 -0.6(5) . . . . ?
C2 C10 C15 C14 176.1(3) . . . . ?
N5 C3 C16 C17 71.4(4) . . . . ?
N4 C3 C16 C17 -174.8(3) . . . . ?
C20 C3 C16 C17 -55.0(4) . . . . ?
C3 C16 C17 C18 53.5(4) . . . . ?
C16 C17 C18 C19 -54.1(5) . . . . ?
C17 C18 C19 C20 55.2(4) . . . . ?
N5 C3 C20 C19 -70.6(4) . . . . ?
N4 C3 C20 C19 175.2(3) . . . . ?
C16 C3 C20 C19 55.6(4) . . . . ?
C18 C19 C20 C3 -55.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049
