# Electronic Supplementary Material (ESI) for Green 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_SHS-618
_database_code_depnum_ccdc_archive 'CCDC 2258313'
loop_
_audit_author_name
_audit_author_address
'Dmitry Vinogradov'
;N D Zelinsky Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2023-03-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N3 O'
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   19.9852(4)
_cell_length_b                   7.55810(10)
_cell_length_c                   20.2911(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3064.97(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.70
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0631 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9329.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0590
0.00 0.00 1.00 0.0250
-1.00 0.00 -1.00 0.1260
1.00 0.00 1.00 0.0290
-1.00 -1.00 0.00 0.1580
1.00 1.00 0.00 0.1840
1.00 -1.00 0.00 0.1180
-1.00 1.00 0.00 0.2630
0.00 1.00 0.00 0.2160

_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.118
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            60450
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.498
_diffrn_reflns_theta_min         2.251
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3933
_reflns_number_total             5095
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5095
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.027
_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)+(0.0574P)²+1.7977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1353
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-N1 \\sim O1A-N3
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.76074(5) 0.74047(14) 0.72584(5) 0.0186(2) Uani 1 1 d D . . . .
N2 N 0.75999(5) 0.70219(15) 0.65977(5) 0.0208(2) Uani 1 1 d . . . . .
N3 N 0.69739(5) 0.67708(14) 0.63764(5) 0.0197(2) Uani 1 1 d D . . . .
C4 C 0.65765(6) 0.69584(15) 0.69024(6) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.69612(6) 0.73427(15) 0.74676(6) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.68034(6) 0.75270(16) 0.81699(6) 0.0178(2) Uani 1 1 d . . . . .
C7 C 0.63357(6) 0.64045(17) 0.84646(7) 0.0233(3) Uani 1 1 d . . . . .
H7 H 0.610416 0.555502 0.820569 0.028 Uiso 1 1 calc R U . . .
C8 C 0.62088(7) 0.6530(2) 0.91366(7) 0.0308(3) Uani 1 1 d . . . . .
H8 H 0.588741 0.576894 0.933337 0.037 Uiso 1 1 calc R U . . .
C9 C 0.65453(8) 0.7749(2) 0.95220(7) 0.0347(3) Uani 1 1 d . . . . .
H9 H 0.645750 0.782378 0.998133 0.042 Uiso 1 1 calc R U . . .
C10 C 0.70117(8) 0.8861(2) 0.92321(7) 0.0320(3) Uani 1 1 d . . . . .
H10 H 0.724517 0.969867 0.949463 0.038 Uiso 1 1 calc R U . . .
C11 C 0.71400(7) 0.87590(18) 0.85609(7) 0.0240(3) Uani 1 1 d . . . . .
H11 H 0.745861 0.953196 0.836654 0.029 Uiso 1 1 calc R U . . .
C12 C 0.58455(6) 0.68225(15) 0.68222(6) 0.0176(2) Uani 1 1 d . . . . .
C13 C 0.55803(6) 0.58363(17) 0.63006(6) 0.0217(2) Uani 1 1 d . . . . .
H13 H 0.587168 0.522206 0.600997 0.026 Uiso 1 1 calc R U . . .
C14 C 0.48923(6) 0.57510(18) 0.62057(7) 0.0246(3) Uani 1 1 d . . . . .
H14 H 0.471575 0.508175 0.584957 0.029 Uiso 1 1 calc R U . . .
C15 C 0.44610(6) 0.66410(17) 0.66296(7) 0.0229(3) Uani 1 1 d . . . . .
H15 H 0.399091 0.658320 0.656334 0.028 Uiso 1 1 calc R U . . .
C16 C 0.47219(6) 0.76154(17) 0.71507(6) 0.0209(2) Uani 1 1 d . . . . .
H16 H 0.442862 0.821793 0.744298 0.025 Uiso 1 1 calc R U . . .
C17 C 0.54104(6) 0.77130(16) 0.72466(6) 0.0188(2) Uani 1 1 d . . . . .
H17 H 0.558516 0.838784 0.760215 0.023 Uiso 1 1 calc R U . . .
C18 C 0.81801(6) 0.69383(16) 0.61920(6) 0.0193(2) Uani 1 1 d . . . . .
C19 C 0.87698(6) 0.62148(16) 0.64356(6) 0.0214(2) Uani 1 1 d . . . . .
H19 H 0.879424 0.579229 0.687593 0.026 Uiso 1 1 calc R U . . .
C20 C 0.93236(6) 0.61222(18) 0.60217(7) 0.0246(3) Uani 1 1 d . . . . .
H20 H 0.973148 0.563938 0.618115 0.030 Uiso 1 1 calc R U . . .
C21 C 0.92844(7) 0.67305(18) 0.53766(7) 0.0253(3) Uani 1 1 d . . . . .
H21 H 0.966567 0.667261 0.509780 0.030 Uiso 1 1 calc R U . . .
C22 C 0.86875(7) 0.74231(19) 0.51400(7) 0.0254(3) Uani 1 1 d . . . . .
H22 H 0.865950 0.781565 0.469609 0.030 Uiso 1 1 calc R U . . .
C23 C 0.81306(6) 0.75464(18) 0.55476(6) 0.0227(2) Uani 1 1 d . . . . .
H23 H 0.772387 0.803714 0.538864 0.027 Uiso 1 1 calc R U . . .
O1 O 0.81417(5) 0.77240(15) 0.75693(5) 0.0244(2) Uani 0.900(2) 1 d D . P A 1
O1A O 0.6843(4) 0.6507(13) 0.5778(2) 0.0244(2) Uani 0.100(2) 1 d D . P A 2


_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 N2 1.3715(14) . ?
N1 C5 1.3603(15) . ?
N1 O1 1.2635(13) . ?
N2 N3 1.3427(14) . ?
N2 C18 1.4234(15) . ?
N3 C4 1.3379(16) . ?
N3 O1A 1.257(3) . ?
C4 C5 1.4108(16) . ?
C4 C12 1.4735(16) . ?
C5 C6 1.4662(17) . ?
C6 C7 1.3968(17) . ?
C6 C11 1.3961(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3901(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3879(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3989(17) . ?
C12 C17 1.3967(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3898(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3913(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3901(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3917(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3902(17) . ?
C18 C23 1.3896(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3911(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.3884(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.3896(18) . ?
C23 H23 0.9500 . ?

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
C5 N1 N2 106.70(9) . . ?
O1 N1 N2 122.52(10) . . ?
O1 N1 C5 130.78(11) . . ?
N1 N2 C18 124.45(10) . . ?
N3 N2 N1 111.52(9) . . ?
N3 N2 C18 124.01(10) . . ?
C4 N3 N2 105.74(10) . . ?
O1A N3 N2 122.7(4) . . ?
O1A N3 C4 131.5(4) . . ?
N3 C4 C5 110.30(10) . . ?
N3 C4 C12 119.54(11) . . ?
C5 C4 C12 130.12(11) . . ?
N1 C5 C4 105.71(10) . . ?
N1 C5 C6 120.28(10) . . ?
C4 C5 C6 133.82(11) . . ?
C7 C6 C5 120.16(11) . . ?
C11 C6 C5 120.81(11) . . ?
C11 C6 C7 118.95(12) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.05(13) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.74(14) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.40(13) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.47(14) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.38(13) . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C4 119.77(11) . . ?
C17 C12 C4 121.03(11) . . ?
C17 C12 C13 119.16(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.30(12) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.32(12) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.61(11) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.35(12) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.26(12) . . ?
C16 C17 H17 119.9 . . ?
C19 C18 N2 120.17(11) . . ?
C23 C18 N2 118.14(11) . . ?
C23 C18 C19 121.67(12) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.66(12) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.49(12) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.92(12) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.50(12) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 118.75(12) . . ?
C18 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?

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
C23 H23 O1A 0.95 2.25 2.732(9) 110.5 . yes

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
N1 N2 N3 C4 -1.24(14) . . . . ?
N1 N2 N3 O1A 175.7(6) . . . . ?
N1 N2 C18 C19 38.48(18) . . . . ?
N1 N2 C18 C23 -143.43(13) . . . . ?
N1 C5 C6 C7 -135.94(12) . . . . ?
N1 C5 C6 C11 40.82(17) . . . . ?
N2 N1 C5 C4 -1.55(12) . . . . ?
N2 N1 C5 C6 174.14(10) . . . . ?
N2 N3 C4 C5 0.21(13) . . . . ?
N2 N3 C4 C12 177.86(10) . . . . ?
N2 C18 C19 C20 178.75(11) . . . . ?
N2 C18 C23 C22 -178.07(12) . . . . ?
N3 N2 C18 C19 -142.98(13) . . . . ?
N3 N2 C18 C23 35.11(18) . . . . ?
N3 C4 C5 N1 0.86(13) . . . . ?
N3 C4 C5 C6 -173.97(12) . . . . ?
N3 C4 C12 C13 25.82(17) . . . . ?
N3 C4 C12 C17 -152.02(12) . . . . ?
C4 C5 C6 C7 38.3(2) . . . . ?
C4 C5 C6 C11 -144.93(14) . . . . ?
C4 C12 C13 C14 -177.66(12) . . . . ?
C4 C12 C17 C16 177.93(11) . . . . ?
C5 N1 N2 N3 1.80(13) . . . . ?
C5 N1 N2 C18 -179.51(11) . . . . ?
C5 C4 C12 C13 -157.06(13) . . . . ?
C5 C4 C12 C17 25.10(19) . . . . ?
C5 C6 C7 C8 177.14(12) . . . . ?
C5 C6 C11 C10 -176.67(12) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C6 C11 C10 0.13(19) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C6 -0.4(2) . . . . ?
C11 C6 C7 C8 0.32(19) . . . . ?
C12 C4 C5 N1 -176.47(12) . . . . ?
C12 C4 C5 C6 8.7(2) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C12 C17 C16 0.08(18) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 0.44(19) . . . . ?
C15 C16 C17 C12 -0.41(18) . . . . ?
C17 C12 C13 C14 0.23(19) . . . . ?
C18 N2 N3 C4 -179.94(11) . . . . ?
C18 N2 N3 O1A -3.0(6) . . . . ?
C18 C19 C20 C21 -0.45(19) . . . . ?
C19 C18 C23 C22 0.0(2) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C20 C21 C22 C23 1.3(2) . . . . ?
C21 C22 C23 C18 -1.0(2) . . . . ?
C23 C18 C19 C20 0.73(19) . . . . ?
O1 N1 N2 N3 -178.63(11) . . . . ?
O1 N1 N2 C18 0.07(19) . . . . ?
O1 N1 C5 C4 178.93(12) . . . . ?
O1 N1 C5 C6 -5.39(19) . . . . ?
O1A N3 C4 C5 -176.4(6) . . . . ?
O1A N3 C4 C12 1.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
