# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1990862'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 N3 O4'
_chemical_formula_sum            'C25 H23 N3 O4'
_chemical_formula_weight         429.46

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                   9.2276(6)
_cell_length_b                   10.5901(7)
_cell_length_c                   11.3733(7)
_cell_angle_alpha                87.0120(10)
_cell_angle_beta                 75.4310(10)
_cell_angle_gamma                77.1710(10)
_cell_volume                     1048.82(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3451
_cell_measurement_theta_min      2
_cell_measurement_theta_max      23.2

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   0.943
_exptl_transmission_factor_max   0.976
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.375
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11114
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.850
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5579
_reflns_number_gt                4459
_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0781P)²+0.0444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5579
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.82516(10) 1.03493(8) 0.59622(8) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.91176(12) 0.88348(10) 0.39940(9) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.29330(11) 1.22778(10) 1.09863(9) 0.0258(2) Uani 1 1 d . . . . .
N2 N 0.94589(12) 0.80228(10) 0.30294(9) 0.0169(2) Uani 1 1 d . . . . .
O3 O 0.46532(10) 0.81017(9) 0.56430(8) 0.0211(2) Uani 1 1 d . . . . .
C3 C 0.82388(14) 0.74929(11) 0.31799(11) 0.0151(2) Uani 1 1 d . . . . .
O4 O 0.53858(10) 0.67368(8) 0.40593(8) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.71102(14) 0.79649(11) 0.42597(11) 0.0143(2) Uani 1 1 d . . . . .
C5 C 0.77458(14) 0.88456(11) 0.47510(10) 0.0143(2) Uani 1 1 d . . . . .
C6 C 0.73247(14) 0.97134(11) 0.58335(11) 0.0144(2) Uani 1 1 d . . . . .
N7 N 0.59546(12) 0.97381(10) 0.65935(9) 0.0154(2) Uani 1 1 d . . . . .
C8 C 0.52824(14) 1.04405(11) 0.76987(11) 0.0151(2) Uani 1 1 d . . . . .
C9 C 0.38336(14) 1.02575(11) 0.83228(11) 0.0172(2) Uani 1 1 d . . . . .
H9A H 0.336060 0.969937 0.799146 0.021 Uiso 1 1 calc R U . . .
C10 C 0.30820(15) 1.08772(12) 0.94139(12) 0.0197(3) Uani 1 1 d . . . . .
H10A H 0.210037 1.074093 0.983370 0.024 Uiso 1 1 calc R U . . .
C11 C 0.37705(15) 1.17079(12) 0.99010(11) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.51975(15) 1.19042(12) 0.92796(11) 0.0186(3) Uani 1 1 d . . . . .
H12A H 0.565869 1.247566 0.960601 0.022 Uiso 1 1 calc R U . . .
C13 C 0.59690(14) 1.12712(12) 0.81764(11) 0.0178(2) Uani 1 1 d . . . . .
H13A H 0.695131 1.140638 0.775716 0.021 Uiso 1 1 calc R U . . .
C14 C 0.36187(18) 1.30846(14) 1.15451(13) 0.0278(3) Uani 1 1 d . . . . .
H14A H 0.291692 1.342017 1.231681 0.042 Uiso 1 1 calc R U . . .
H14B H 0.382993 1.380933 1.100578 0.042 Uiso 1 1 calc R U . . .
H14C H 0.458045 1.257891 1.169658 0.042 Uiso 1 1 calc R U . . .
C15 C 0.56127(14) 0.76316(11) 0.47349(11) 0.0151(2) Uani 1 1 d . . . . .
C16 C 0.38653(15) 0.64324(12) 0.44042(12) 0.0198(3) Uani 1 1 d . . . . .
H16A H 0.306038 0.723171 0.443565 0.024 Uiso 1 1 calc R U . . .
H16B H 0.369648 0.601935 0.521408 0.024 Uiso 1 1 calc R U . . .
C17 C 0.38117(17) 0.55156(14) 0.34492(13) 0.0260(3) Uani 1 1 d . . . . .
H17A H 0.280869 0.528104 0.365014 0.039 Uiso 1 1 calc R U . . .
H17B H 0.461841 0.473243 0.342407 0.039 Uiso 1 1 calc R U . . .
H17C H 0.397335 0.593875 0.265413 0.039 Uiso 1 1 calc R U . . .
C18 C 0.82276(14) 0.65570(11) 0.22392(11) 0.0160(2) Uani 1 1 d . . . . .
H18A H 0.892202 0.673744 0.146208 0.019 Uiso 1 1 calc R U . . .
H18B H 0.717966 0.671204 0.211228 0.019 Uiso 1 1 calc R U . . .
C19 C 0.87115(13) 0.51387(11) 0.25522(11) 0.0158(2) Uani 1 1 d . . . . .
C20 C 0.92364(15) 0.47533(12) 0.35697(12) 0.0196(3) Uani 1 1 d . . . . .
H20A H 0.930674 0.539189 0.409689 0.023 Uiso 1 1 calc R U . . .
C21 C 0.96745(16) 0.34306(13) 0.38518(12) 0.0233(3) Uani 1 1 d . . . . .
H21A H 1.003216 0.319262 0.456289 0.028 Uiso 1 1 calc R U . . .
C22 C 0.95877(15) 0.24937(13) 0.31112(13) 0.0225(3) Uani 1 1 d . . . . .
H22A H 0.987139 0.160679 0.331409 0.027 Uiso 1 1 calc R U . . .
C23 C 0.90762(14) 0.28370(12) 0.20397(12) 0.0181(2) Uani 1 1 d . . . . .
C24 C 0.86380(13) 0.41700(11) 0.17446(11) 0.0160(2) Uani 1 1 d . . . . .
C25 C 0.90197(15) 0.18770(12) 0.12329(13) 0.0219(3) Uani 1 1 d . . . . .
H25A H 0.928689 0.098756 0.143295 0.026 Uiso 1 1 calc R U . . .
C26 C 0.85868(15) 0.22131(13) 0.01730(13) 0.0243(3) Uani 1 1 d . . . . .
H26A H 0.857330 0.155915 -0.036262 0.029 Uiso 1 1 calc R U . . .
C27 C 0.81602(15) 0.35325(13) -0.01240(12) 0.0230(3) Uani 1 1 d . . . . .
H27A H 0.785694 0.376254 -0.085890 0.028 Uiso 1 1 calc R U . . .
C28 C 0.81809(15) 0.44872(12) 0.06436(11) 0.0194(3) Uani 1 1 d . . . . .
H28A H 0.788528 0.537065 0.043422 0.023 Uiso 1 1 calc R U . . .
H1N H 0.984(2) 0.9268(16) 0.4105(15) 0.029(4) Uiso 1 1 d . . . . .
H7N H 0.537(2) 0.9204(18) 0.6371(16) 0.037(5) 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
O1 C6 1.2391(14) . ?
N1 C5 1.3379(16) . ?
N1 N2 1.3588(13) . ?
N1 H1N 0.927(18) . ?
O2 C11 1.3696(15) . ?
O2 C14 1.4259(16) . ?
N2 C3 1.3362(16) . ?
O3 C15 1.2232(15) . ?
C3 C4 1.4255(17) . ?
C3 C18 1.4993(16) . ?
O4 C15 1.3330(14) . ?
O4 C16 1.4619(15) . ?
C4 C5 1.4100(16) . ?
C4 C15 1.4653(17) . ?
C5 C6 1.4934(16) . ?
C6 N7 1.3357(16) . ?
N7 C8 1.4207(15) . ?
N7 H7N 0.946(19) . ?
C8 C13 1.3932(16) . ?
C8 C9 1.3971(18) . ?
C9 C10 1.3789(17) . ?
C9 H9A 0.9500 . ?
C10 C11 1.4002(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3837(19) . ?
C12 C13 1.3988(17) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.5109(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.5194(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.3730(17) . ?
C19 C24 1.4356(16) . ?
C20 C21 1.4125(18) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3627(18) . ?
C21 H21A 0.9500 . ?
C22 C23 1.4167(18) . ?
C22 H22A 0.9500 . ?
C23 C25 1.4224(17) . ?
C23 C24 1.4263(17) . ?
C24 C28 1.4206(17) . ?
C25 C26 1.3688(19) . ?
C25 H25A 0.9500 . ?
C26 C27 1.4124(19) . ?
C26 H26A 0.9500 . ?
C27 C28 1.3760(17) . ?
C27 H27A 0.9500 . ?
C28 H28A 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 113.75(10) . . ?
C5 N1 H1N 126.3(10) . . ?
N2 N1 H1N 119.7(10) . . ?
C11 O2 C14 117.35(11) . . ?
C3 N2 N1 104.82(10) . . ?
N2 C3 C4 111.01(10) . . ?
N2 C3 C18 118.59(11) . . ?
C4 C3 C18 130.39(11) . . ?
C15 O4 C16 115.93(10) . . ?
C5 C4 C3 104.40(11) . . ?
C5 C4 C15 127.87(11) . . ?
C3 C4 C15 127.71(11) . . ?
N1 C5 C4 106.00(10) . . ?
N1 C5 C6 115.77(10) . . ?
C4 C5 C6 138.21(11) . . ?
O1 C6 N7 125.09(11) . . ?
O1 C6 C5 118.54(11) . . ?
N7 C6 C5 116.38(10) . . ?
C6 N7 C8 128.38(10) . . ?
C6 N7 H7N 115.4(11) . . ?
C8 N7 H7N 116.2(11) . . ?
C13 C8 C9 119.65(11) . . ?
C13 C8 N7 124.53(11) . . ?
C9 C8 N7 115.82(11) . . ?
C10 C9 C8 120.80(11) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 119.77(12) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
O2 C11 C12 124.98(11) . . ?
O2 C11 C10 115.37(12) . . ?
C12 C11 C10 119.66(12) . . ?
C11 C12 C13 120.79(11) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C8 C13 C12 119.33(12) . . ?
C8 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 122.29(11) . . ?
O3 C15 C4 125.39(11) . . ?
O4 C15 C4 112.32(10) . . ?
O4 C16 C17 106.82(11) . . ?
O4 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O4 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 C19 114.72(9) . . ?
C3 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
C3 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C24 118.98(11) . . ?
C20 C19 C18 122.29(10) . . ?
C24 C19 C18 118.72(10) . . ?
C19 C20 C21 121.63(11) . . ?
C19 C20 H20A 119.2 . . ?
C21 C20 H20A 119.2 . . ?
C22 C21 C20 120.46(12) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 120.26(12) . . ?
C21 C22 H22A 119.9 . . ?
C23 C22 H22A 119.9 . . ?
C22 C23 C25 121.33(12) . . ?
C22 C23 C24 119.67(11) . . ?
C25 C23 C24 118.99(11) . . ?
C28 C24 C23 118.52(11) . . ?
C28 C24 C19 122.47(11) . . ?
C23 C24 C19 118.98(11) . . ?
C26 C25 C23 121.11(12) . . ?
C26 C25 H25A 119.4 . . ?
C23 C25 H25A 119.4 . . ?
C25 C26 C27 119.97(12) . . ?
C25 C26 H26A 120.0 . . ?
C27 C26 H26A 120.0 . . ?
C28 C27 C26 120.47(12) . . ?
C28 C27 H27A 119.8 . . ?
C26 C27 H27A 119.8 . . ?
C27 C28 C24 120.91(12) . . ?
C27 C28 H28A 119.5 . . ?
C24 C28 H28A 119.5 . . ?

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
C5 N1 N2 C3 0.17(13) . . . . ?
N1 N2 C3 C4 -0.49(13) . . . . ?
N1 N2 C3 C18 178.55(10) . . . . ?
N2 C3 C4 C5 0.62(13) . . . . ?
C18 C3 C4 C5 -178.27(11) . . . . ?
N2 C3 C4 C15 179.33(11) . . . . ?
C18 C3 C4 C15 0.4(2) . . . . ?
N2 N1 C5 C4 0.22(13) . . . . ?
N2 N1 C5 C6 179.37(9) . . . . ?
C3 C4 C5 N1 -0.49(12) . . . . ?
C15 C4 C5 N1 -179.20(11) . . . . ?
C3 C4 C5 C6 -179.34(13) . . . . ?
C15 C4 C5 C6 1.9(2) . . . . ?
N1 C5 C6 O1 -0.28(16) . . . . ?
C4 C5 C6 O1 178.50(13) . . . . ?
N1 C5 C6 N7 179.67(10) . . . . ?
C4 C5 C6 N7 -1.5(2) . . . . ?
O1 C6 N7 C8 -1.87(19) . . . . ?
C5 C6 N7 C8 178.18(10) . . . . ?
C6 N7 C8 C13 1.20(19) . . . . ?
C6 N7 C8 C9 -178.71(11) . . . . ?
C13 C8 C9 C10 -0.79(18) . . . . ?
N7 C8 C9 C10 179.13(11) . . . . ?
C8 C9 C10 C11 0.46(18) . . . . ?
C14 O2 C11 C12 -3.23(19) . . . . ?
C14 O2 C11 C10 177.16(11) . . . . ?
C9 C10 C11 O2 179.93(11) . . . . ?
C9 C10 C11 C12 0.29(19) . . . . ?
O2 C11 C12 C13 179.68(11) . . . . ?
C10 C11 C12 C13 -0.72(19) . . . . ?
C9 C8 C13 C12 0.36(18) . . . . ?
N7 C8 C13 C12 -179.55(11) . . . . ?
C11 C12 C13 C8 0.39(18) . . . . ?
C16 O4 C15 O3 5.30(16) . . . . ?
C16 O4 C15 C4 -174.63(9) . . . . ?
C5 C4 C15 O3 1.53(19) . . . . ?
C3 C4 C15 O3 -176.89(12) . . . . ?
C5 C4 C15 O4 -178.55(11) . . . . ?
C3 C4 C15 O4 3.03(16) . . . . ?
C15 O4 C16 C17 174.13(10) . . . . ?
N2 C3 C18 C19 97.42(13) . . . . ?
C4 C3 C18 C19 -83.75(15) . . . . ?
C3 C18 C19 C20 -5.09(17) . . . . ?
C3 C18 C19 C24 175.88(11) . . . . ?
C24 C19 C20 C21 -1.31(19) . . . . ?
C18 C19 C20 C21 179.66(12) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C23 0.9(2) . . . . ?
C21 C22 C23 C25 178.06(13) . . . . ?
C21 C22 C23 C24 -0.6(2) . . . . ?
C22 C23 C24 C28 177.82(12) . . . . ?
C25 C23 C24 C28 -0.86(18) . . . . ?
C22 C23 C24 C19 -0.63(18) . . . . ?
C25 C23 C24 C19 -179.31(11) . . . . ?
C20 C19 C24 C28 -176.83(12) . . . . ?
C18 C19 C24 C28 2.23(18) . . . . ?
C20 C19 C24 C23 1.56(18) . . . . ?
C18 C19 C24 C23 -179.38(11) . . . . ?
C22 C23 C25 C26 -177.19(13) . . . . ?
C24 C23 C25 C26 1.46(19) . . . . ?
C23 C25 C26 C27 -1.1(2) . . . . ?
C25 C26 C27 C28 0.2(2) . . . . ?
C26 C27 C28 C24 0.4(2) . . . . ?
C23 C24 C28 C27 -0.03(19) . . . . ?
C19 C24 C28 C27 178.36(12) . . . . ?

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
N1 H1N O1 0.927(18) 1.873(18) 2.7640(14) 160.5(15) 2_776
N7 H7N O3 0.946(19) 1.790(19) 2.7178(13) 166.1(17) .

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.265



####################################################################### 
# 
# 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_anko_417
_database_code_depnum_ccdc_archive 'CCDC 1990863'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N3 O4'
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32

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      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                   11.5210(8)
_cell_length_b                   7.7967(6)
_cell_length_c                   15.9176(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.3708(14)
_cell_angle_gamma                90
_cell_volume                     1429.40(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4320
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.945
_exptl_transmission_factor_max   0.988
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16729
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3809
_reflns_number_gt                3306
_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0525P)²+0.5551P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0072(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3809
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_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 0.67251(7) 0.46627(10) 0.62466(5) 0.01915(18) Uani 1 1 d . . . . .
N1 N 0.80497(8) 0.01833(12) 0.70271(6) 0.01623(19) Uani 1 1 d . . . . .
H1 H 0.8112(13) -0.019(2) 0.7576(10) 0.029(4) Uiso 1 1 d . . . . .
O2 O 0.54343(8) 0.93264(10) 0.29534(5) 0.02258(19) Uani 1 1 d . . . . .
N2 N 0.75638(8) 0.17373(12) 0.68809(5) 0.01632(19) Uani 1 1 d . . . . .
O3 O 0.80193(7) 0.10025(10) 0.41750(5) 0.01955(18) Uani 1 1 d . . . . .
C3 C 0.75667(9) 0.19258(13) 0.60489(6) 0.0139(2) Uani 1 1 d . . . . .
O4 O 0.88860(7) -0.13588(10) 0.46940(5) 0.01819(17) Uani 1 1 d . . . . .
C4 C 0.80775(8) 0.04626(13) 0.56603(6) 0.0135(2) Uani 1 1 d . . . . .
C5 C 0.83752(9) -0.06338(14) 0.63287(6) 0.0146(2) Uani 1 1 d . . . . .
C6 C 0.70530(9) 0.35815(13) 0.57383(6) 0.0141(2) Uani 1 1 d . . . . .
N7 N 0.69831(8) 0.37834(12) 0.48961(5) 0.01499(19) Uani 1 1 d . . . . .
H7 H 0.7294(12) 0.293(2) 0.4599(9) 0.025(4) Uiso 1 1 d . . . . .
C8 C 0.65459(9) 0.52225(13) 0.44462(6) 0.0146(2) Uani 1 1 d . . . . .
C9 C 0.61014(10) 0.66764(15) 0.48279(7) 0.0190(2) Uani 1 1 d . . . . .
H9 H 0.605784 0.672892 0.542256 0.023 Uiso 1 1 calc R U . . .
C10 C 0.57196(10) 0.80574(15) 0.43388(7) 0.0191(2) Uani 1 1 d . . . . .
H10 H 0.541887 0.904827 0.460435 0.023 Uiso 1 1 calc R U . . .
C11 C 0.57727(9) 0.80043(14) 0.34703(7) 0.0169(2) Uani 1 1 d . . . . .
C12 C 0.62074(10) 0.65380(14) 0.30834(7) 0.0185(2) Uani 1 1 d . . . . .
H12 H 0.624019 0.648215 0.248821 0.022 Uiso 1 1 calc R U . . .
C13 C 0.65901(9) 0.51674(14) 0.35675(6) 0.0169(2) Uani 1 1 d . . . . .
H13 H 0.688683 0.417528 0.330072 0.020 Uiso 1 1 calc R U . . .
C14 C 0.49567(11) 1.08102(15) 0.33449(8) 0.0240(2) Uani 1 1 d . . . . .
H14A H 0.471226 1.163751 0.291225 0.036 Uiso 1 1 calc R U . . .
H14B H 0.554588 1.133530 0.371728 0.036 Uiso 1 1 calc R U . . .
H14C H 0.428490 1.047443 0.367337 0.036 Uiso 1 1 calc R U . . .
C15 C 0.83070(9) 0.01066(13) 0.47756(6) 0.0142(2) Uani 1 1 d . . . . .
C16 C 0.90654(9) -0.20072(14) 0.38520(6) 0.0178(2) Uani 1 1 d . . . . .
H16A H 0.961148 -0.126347 0.354834 0.021 Uiso 1 1 calc R U . . .
H16B H 0.832133 -0.205736 0.352870 0.021 Uiso 1 1 calc R U . . .
C17 C 0.95663(10) -0.37820(15) 0.39713(7) 0.0226(2) Uani 1 1 d . . . . .
H17A H 0.967835 -0.431352 0.342127 0.034 Uiso 1 1 calc R U . . .
H17B H 0.903091 -0.448202 0.429579 0.034 Uiso 1 1 calc R U . . .
H17C H 1.031487 -0.370258 0.427439 0.034 Uiso 1 1 calc R U . . .
C18 C 0.89435(9) -0.23508(14) 0.63793(7) 0.0182(2) Uani 1 1 d . . . . .
H18A H 0.898135 -0.273234 0.696595 0.027 Uiso 1 1 calc R U . . .
H18B H 0.973108 -0.227145 0.616313 0.027 Uiso 1 1 calc R U . . .
H18C H 0.849165 -0.317664 0.604212 0.027 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 1.2339(13) . ?
N1 C5 1.3425(13) . ?
N1 N2 1.3526(13) . ?
N1 H1 0.922(16) . ?
O2 C11 1.3697(12) . ?
O2 C14 1.4303(14) . ?
N2 C3 1.3326(13) . ?
O3 C15 1.2233(13) . ?
C3 C4 1.4309(14) . ?
C3 C6 1.4990(14) . ?
O4 C15 1.3309(13) . ?
O4 C16 1.4519(12) . ?
C4 C5 1.4011(14) . ?
C4 C15 1.4655(14) . ?
C5 C18 1.4915(15) . ?
C6 N7 1.3503(13) . ?
N7 C8 1.4172(13) . ?
N7 H7 0.898(16) . ?
C8 C9 1.3897(15) . ?
C8 C13 1.4014(14) . ?
C9 C10 1.3938(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.3859(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.3971(15) . ?
C12 C13 1.3835(15) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.5095(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C5 N1 N2 113.91(9) . . ?
C5 N1 H1 128.1(10) . . ?
N2 N1 H1 118.0(10) . . ?
C11 O2 C14 117.00(9) . . ?
C3 N2 N1 105.00(8) . . ?
N2 C3 C4 110.64(9) . . ?
N2 C3 C6 114.35(9) . . ?
C4 C3 C6 135.01(9) . . ?
C15 O4 C16 118.15(8) . . ?
C5 C4 C3 104.71(9) . . ?
C5 C4 C15 124.58(9) . . ?
C3 C4 C15 130.68(9) . . ?
N1 C5 C4 105.73(9) . . ?
N1 C5 C18 120.81(9) . . ?
C4 C5 C18 133.45(9) . . ?
O1 C6 N7 124.02(10) . . ?
O1 C6 C3 119.78(9) . . ?
N7 C6 C3 116.20(9) . . ?
C6 N7 C8 127.31(9) . . ?
C6 N7 H7 114.9(9) . . ?
C8 N7 H7 117.7(9) . . ?
C9 C8 C13 118.94(10) . . ?
C9 C8 N7 123.72(9) . . ?
C13 C8 N7 117.33(9) . . ?
C8 C9 C10 120.04(10) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.88(10) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
O2 C11 C10 123.91(10) . . ?
O2 C11 C12 116.80(9) . . ?
C10 C11 C12 119.28(10) . . ?
C13 C12 C11 119.95(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.90(10) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 122.75(9) . . ?
O3 C15 C4 126.23(10) . . ?
O4 C15 C4 111.03(9) . . ?
O4 C16 C17 105.39(9) . . ?
O4 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
O4 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C5 N1 N2 C3 0.54(12) . . . . ?
N1 N2 C3 C4 -0.59(11) . . . . ?
N1 N2 C3 C6 179.66(8) . . . . ?
N2 C3 C4 C5 0.45(11) . . . . ?
C6 C3 C4 C5 -179.88(11) . . . . ?
N2 C3 C4 C15 -177.68(10) . . . . ?
C6 C3 C4 C15 1.99(19) . . . . ?
N2 N1 C5 C4 -0.26(12) . . . . ?
N2 N1 C5 C18 179.00(9) . . . . ?
C3 C4 C5 N1 -0.11(11) . . . . ?
C15 C4 C5 N1 178.16(9) . . . . ?
C3 C4 C5 C18 -179.24(11) . . . . ?
C15 C4 C5 C18 -0.96(18) . . . . ?
N2 C3 C6 O1 3.46(14) . . . . ?
C4 C3 C6 O1 -176.21(11) . . . . ?
N2 C3 C6 N7 -176.60(9) . . . . ?
C4 C3 C6 N7 3.73(17) . . . . ?
O1 C6 N7 C8 0.52(17) . . . . ?
C3 C6 N7 C8 -179.42(9) . . . . ?
C6 N7 C8 C9 -0.63(17) . . . . ?
C6 N7 C8 C13 178.20(10) . . . . ?
C13 C8 C9 C10 -0.67(16) . . . . ?
N7 C8 C9 C10 178.13(10) . . . . ?
C8 C9 C10 C11 0.18(17) . . . . ?
C14 O2 C11 C10 -2.61(16) . . . . ?
C14 O2 C11 C12 178.20(10) . . . . ?
C9 C10 C11 O2 -178.67(10) . . . . ?
C9 C10 C11 C12 0.50(17) . . . . ?
O2 C11 C12 C13 178.55(10) . . . . ?
C10 C11 C12 C13 -0.68(16) . . . . ?
C11 C12 C13 C8 0.18(17) . . . . ?
C9 C8 C13 C12 0.49(16) . . . . ?
N7 C8 C13 C12 -178.39(10) . . . . ?
C16 O4 C15 O3 -7.09(15) . . . . ?
C16 O4 C15 C4 172.88(8) . . . . ?
C5 C4 C15 O3 176.97(10) . . . . ?
C3 C4 C15 O3 -5.23(18) . . . . ?
C5 C4 C15 O4 -3.00(14) . . . . ?
C3 C4 C15 O4 174.80(10) . . . . ?
C15 O4 C16 C17 -171.34(9) . . . . ?

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
C18 H18A O2 0.98 2.59 3.3756(13) 137.6 4_666
C18 H18A N2 0.98 2.62 3.3794(14) 134.4 2_646
C9 H9 O1 0.95 2.20 2.8290(13) 122.4 .
C17 H17A O2 0.98 2.43 3.4002(14) 169.4 2_635
N7 H7 O3 0.898(16) 1.852(16) 2.7402(12) 169.6(14) .
N1 H1 O1 0.922(16) 1.883(17) 2.7836(12) 165.0(14) 2_646

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046



