# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2025

####################################################################### 
# 
# 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_191rs
_database_code_depnum_ccdc_archive 'CCDC 2430089'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C12 H17 N4 O2'
_chemical_formula_weight         249.29

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.510(4)
_cell_length_b                   12.545(2)
_cell_length_c                   17.886(3)
_cell_angle_alpha                90
_cell_angle_beta                 120.486(8)
_cell_angle_gamma                90
_cell_volume                     5319.6(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2641
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      20.26

_exptl_crystal_description       rhombic_prism
_exptl_crystal_colour            dark_blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             2128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5020
_exptl_absorpt_correction_T_max  0.5568
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22259
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5422
_reflns_number_gt                2399
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0416P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5422
_refine_ls_number_parameters     428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   0.821
_refine_ls_restrained_S_all      0.821
_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
O1A O 0.04421(5) 0.46171(10) 0.15604(10) 0.0558(4) Uani 1 1 d . . . . .
N2A N -0.00338(7) 0.51068(12) 0.12424(11) 0.0423(4) Uani 1 1 d . . . . .
C3A C -0.05843(8) 0.45172(16) 0.07656(13) 0.0440(5) Uani 1 1 d . . . . .
C4A C -0.05736(11) 0.3827(2) 0.00778(17) 0.0591(7) Uani 1 1 d . . . . .
H4AA H -0.0923(10) 0.3488(18) -0.0249(15) 0.089 Uiso 1 1 d . U . . .
H4AB H -0.0510(9) 0.4264(18) -0.0336(15) 0.089 Uiso 1 1 d . U . . .
H4AC H -0.0248(10) 0.3293(17) 0.0412(15) 0.089 Uiso 1 1 d . U . . .
C5A C -0.06271(11) 0.3821(2) 0.14246(17) 0.0658(8) Uani 1 1 d . . . . .
H5AA H -0.0983(10) 0.3452(18) 0.1132(16) 0.099 Uiso 1 1 d . U . . .
H5AB H -0.0299(10) 0.3306(18) 0.1690(16) 0.099 Uiso 1 1 d . U . . .
H5AC H -0.0616(10) 0.4263(19) 0.1896(17) 0.099 Uiso 1 1 d . U . . .
C6A C -0.10094(9) 0.54669(17) 0.04113(15) 0.0521(6) Uani 1 1 d . . . . .
C7A C -0.12316(12) 0.5717(3) -0.05526(19) 0.0828(9) Uani 1 1 d . . . . .
H7AA H -0.1491(11) 0.509(2) -0.0880(19) 0.124 Uiso 1 1 d . U . . .
H7AB H -0.1462(11) 0.639(2) -0.0686(18) 0.124 Uiso 1 1 d . U . . .
H7AC H -0.0890(12) 0.582(2) -0.0637(18) 0.124 Uiso 1 1 d . U . . .
C8A C -0.15008(12) 0.5394(3) 0.0571(3) 0.0988(12) Uani 1 1 d . . . . .
H8AA H -0.1710(13) 0.475(2) 0.031(2) 0.148 Uiso 1 1 d . U . . .
H8AB H -0.1335(13) 0.530(3) 0.120(2) 0.148 Uiso 1 1 d . U . . .
H8AC H -0.1703(13) 0.602(3) 0.036(2) 0.148 Uiso 1 1 d . U . . .
N9A N -0.06439(7) 0.63815(14) 0.09108(12) 0.0556(5) Uani 1 1 d . . . . .
O10A O -0.08497(6) 0.73103(13) 0.08662(12) 0.0906(6) Uani 1 1 d . . . . .
C11A C -0.00884(8) 0.61464(16) 0.13311(13) 0.0423(5) Uani 1 1 d . . . . .
C12A C 0.03637(9) 0.68950(15) 0.17604(13) 0.0424(5) Uani 1 1 d . . . . .
C13A C 0.03349(10) 0.80015(17) 0.18639(17) 0.0583(7) Uani 1 1 d . . . . .
H13A H 0.0011(8) 0.8409(16) 0.1688(13) 0.070 Uiso 1 1 d . U . . .
N14A N 0.08368(8) 0.84575(13) 0.22547(13) 0.0596(5) Uani 1 1 d . . . . .
N15A N 0.11974(7) 0.76404(13) 0.24061(11) 0.0488(5) Uani 1 1 d . . . . .
C16A C 0.17820(10) 0.7813(2) 0.27726(16) 0.0634(7) Uani 1 1 d . . . . .
H16A H 0.1981(8) 0.7102(17) 0.2805(13) 0.076 Uiso 1 1 d . U . . .
C17A C 0.20212(11) 0.8746(2) 0.29926(19) 0.0747(9) Uani 1 1 d . . . . .
H17A H 0.1812(9) 0.9394(18) 0.2926(15) 0.090 Uiso 1 1 d . U . . .
H17B H 0.2416(10) 0.8771(18) 0.3238(16) 0.090 Uiso 1 1 d . U . . .
C18A C 0.09301(9) 0.67032(17) 0.21290(14) 0.0455(6) Uani 1 1 d . . . . .
H18A H 0.1123(8) 0.6078(15) 0.2180(12) 0.055 Uiso 1 1 d . U . . .
O1B O 0.21699(6) 1.53048(11) 0.30968(11) 0.0710(5) Uani 1 1 d . . . . .
N2B N 0.26134(7) 1.48566(13) 0.37072(12) 0.0489(5) Uani 1 1 d . . . . .
C3B C 0.31219(8) 1.54810(16) 0.43427(14) 0.0495(6) Uani 1 1 d . . . . .
C4B C 0.32785(12) 1.6263(2) 0.3856(2) 0.0704(8) Uani 1 1 d . . . . .
H4BA H 0.3638(10) 1.6644(19) 0.4295(17) 0.106 Uiso 1 1 d . U . . .
H4BB H 0.3333(11) 1.591(2) 0.3411(17) 0.106 Uiso 1 1 d . U . . .
H4BC H 0.2977(10) 1.6788(19) 0.3567(17) 0.106 Uiso 1 1 d . U . . .
C5B C 0.29520(12) 1.6070(2) 0.4916(2) 0.0770(9) Uani 1 1 d . . . . .
H5BA H 0.3270(11) 1.650(2) 0.5356(17) 0.115 Uiso 1 1 d . U . . .
H5BB H 0.2635(11) 1.654(2) 0.4552(18) 0.115 Uiso 1 1 d . U . . .
H5BC H 0.2864(11) 1.555(2) 0.5238(18) 0.115 Uiso 1 1 d . U . . .
C6B C 0.35544(8) 1.45709(17) 0.48115(14) 0.0517(6) Uani 1 1 d . . . . .
C7B C 0.39449(12) 1.4359(3) 0.4450(2) 0.0778(9) Uani 1 1 d . . . . .
H7BA H 0.4189(11) 1.497(2) 0.4574(18) 0.117 Uiso 1 1 d . U . . .
H7BB H 0.4141(11) 1.368(2) 0.4724(18) 0.117 Uiso 1 1 d . U . . .
H7BC H 0.3722(11) 1.427(2) 0.3811(18) 0.117 Uiso 1 1 d . U . . .
C8B C 0.39033(12) 1.4670(3) 0.57918(19) 0.0813(9) Uani 1 1 d . . . . .
H8BA H 0.4118(11) 1.533(2) 0.5936(18) 0.122 Uiso 1 1 d . U . . .
H8BB H 0.3657(12) 1.474(2) 0.6059(18) 0.122 Uiso 1 1 d . U . . .
H8BC H 0.4141(11) 1.402(2) 0.6009(19) 0.122 Uiso 1 1 d . U . . .
N9B N 0.31727(7) 1.36302(14) 0.45705(13) 0.0585(5) Uani 1 1 d . . . . .
O10B O 0.33561(7) 1.27166(14) 0.49190(12) 0.0929(6) Uani 1 1 d . . . . .
C11B C 0.26523(9) 1.38233(16) 0.39060(14) 0.0465(6) Uani 1 1 d . . . . .
C12B C 0.22121(8) 1.30500(15) 0.34861(14) 0.0451(6) Uani 1 1 d . . . . .
C13B C 0.22321(10) 1.19459(18) 0.36387(17) 0.0632(7) Uani 1 1 d . . . . .
H13B H 0.2547(9) 1.1532(16) 0.4044(14) 0.076 Uiso 1 1 d . U . . .
N14B N 0.17419(8) 1.14770(13) 0.31382(13) 0.0610(5) Uani 1 1 d . . . . .
N15B N 0.13965(7) 1.22815(13) 0.26547(11) 0.0471(5) Uani 1 1 d . . . . .
C16B C 0.08247(9) 1.21016(19) 0.20357(16) 0.0599(7) Uani 1 1 d . . . . .
H16B H 0.0642(8) 1.2788(17) 0.1724(14) 0.072 Uiso 1 1 d . U . . .
C17B C 0.05818(11) 1.1176(2) 0.1867(2) 0.0763(9) Uani 1 1 d . . . . .
H17C H 0.0811(9) 1.0525(18) 0.2184(15) 0.092 Uiso 1 1 d . U . . .
H17D H 0.0185(10) 1.1121(18) 0.1434(15) 0.092 Uiso 1 1 d . U . . .
C18B C 0.16642(9) 1.32246(16) 0.28439(15) 0.0464(6) Uani 1 1 d . . . . .
H18B H 0.1481(8) 1.3841(15) 0.2578(12) 0.056 Uiso 1 1 d . 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
O1A N2A 1.2882(18) . ?
N2A C11A 1.332(2) . ?
N2A C3A 1.503(2) . ?
C3A C4A 1.517(3) . ?
C3A C5A 1.519(3) . ?
C3A C6A 1.561(3) . ?
C6A N9A 1.488(2) . ?
C6A C8A 1.520(4) . ?
C6A C7A 1.541(4) . ?
N9A O10A 1.280(2) . ?
N9A C11A 1.350(2) . ?
C11A C12A 1.432(3) . ?
C12A C18A 1.371(3) . ?
C12A C13A 1.408(3) . ?
C13A N14A 1.320(3) . ?
N14A N15A 1.355(2) . ?
N15A C18A 1.341(2) . ?
N15A C16A 1.412(3) . ?
C16A C17A 1.302(3) . ?
O1B N2B 1.2827(19) . ?
N2B C11B 1.334(2) . ?
N2B C3B 1.500(2) . ?
C3B C4B 1.512(3) . ?
C3B C5B 1.517(3) . ?
C3B C6B 1.552(3) . ?
C6B N9B 1.491(2) . ?
C6B C8B 1.518(3) . ?
C6B C7B 1.532(3) . ?
N9B O10B 1.280(2) . ?
N9B C11B 1.340(2) . ?
C11B C12B 1.431(3) . ?
C12B C18B 1.372(3) . ?
C12B C13B 1.407(3) . ?
C13B N14B 1.320(3) . ?
N14B N15B 1.355(2) . ?
N15B C18B 1.343(2) . ?
N15B C16B 1.409(3) . ?
C16B C17B 1.296(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
O1A N2A C11A 124.43(16) . . ?
O1A N2A C3A 121.45(15) . . ?
C11A N2A C3A 114.06(16) . . ?
N2A C3A C4A 108.21(17) . . ?
N2A C3A C5A 107.18(17) . . ?
C4A C3A C5A 110.0(2) . . ?
N2A C3A C6A 100.74(15) . . ?
C4A C3A C6A 115.16(19) . . ?
C5A C3A C6A 114.65(19) . . ?
N9A C6A C8A 109.2(2) . . ?
N9A C6A C7A 106.1(2) . . ?
C8A C6A C7A 109.7(2) . . ?
N9A C6A C3A 101.88(16) . . ?
C8A C6A C3A 115.6(2) . . ?
C7A C6A C3A 113.6(2) . . ?
O10A N9A C11A 124.99(18) . . ?
O10A N9A C6A 121.44(17) . . ?
C11A N9A C6A 113.28(16) . . ?
N2A C11A N9A 108.17(18) . . ?
N2A C11A C12A 125.91(18) . . ?
N9A C11A C12A 125.84(18) . . ?
C18A C12A C13A 103.65(19) . . ?
C18A C12A C11A 127.54(18) . . ?
C13A C12A C11A 128.7(2) . . ?
N14A C13A C12A 112.5(2) . . ?
C13A N14A N15A 103.94(17) . . ?
C18A N15A N14A 112.40(17) . . ?
C18A N15A C16A 125.99(19) . . ?
N14A N15A C16A 121.52(18) . . ?
C17A C16A N15A 124.1(2) . . ?
N15A C18A C12A 107.46(18) . . ?
O1B N2B C11B 124.47(17) . . ?
O1B N2B C3B 122.34(16) . . ?
C11B N2B C3B 112.80(17) . . ?
N2B C3B C4B 109.33(19) . . ?
N2B C3B C5B 106.13(18) . . ?
C4B C3B C5B 110.4(2) . . ?
N2B C3B C6B 100.95(16) . . ?
C4B C3B C6B 115.08(19) . . ?
C5B C3B C6B 114.1(2) . . ?
N9B C6B C8B 109.8(2) . . ?
N9B C6B C7B 106.4(2) . . ?
C8B C6B C7B 109.5(2) . . ?
N9B C6B C3B 101.05(15) . . ?
C8B C6B C3B 115.2(2) . . ?
C7B C6B C3B 114.2(2) . . ?
O10B N9B C11B 125.02(18) . . ?
O10B N9B C6B 121.50(17) . . ?
C11B N9B C6B 113.11(17) . . ?
N2B C11B N9B 108.50(18) . . ?
N2B C11B C12B 125.91(19) . . ?
N9B C11B C12B 125.59(19) . . ?
C18B C12B C13B 103.7(2) . . ?
C18B C12B C11B 127.51(19) . . ?
C13B C12B C11B 128.7(2) . . ?
N14B C13B C12B 112.4(2) . . ?
C13B N14B N15B 104.20(16) . . ?
C18B N15B N14B 112.22(17) . . ?
C18B N15B C16B 126.17(19) . . ?
N14B N15B C16B 121.61(18) . . ?
C17B C16B N15B 124.4(2) . . ?
N15B C18B C12B 107.42(19) . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_957xs
_database_code_depnum_ccdc_archive 'CCDC 2430092'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C12 H18 Br N4 O2'
_chemical_formula_weight         330.21

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'
Br Br -0.2901 2.4595 '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                   6.4390(5)
_cell_length_b                   11.1141(9)
_cell_length_c                   11.5261(9)
_cell_angle_alpha                62.947(6)
_cell_angle_beta                 76.883(6)
_cell_angle_gamma                89.549(5)
_cell_volume                     711.10(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    3519
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      22.71

_exptl_crystal_description       plate
_exptl_crystal_colour            green_blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             338
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.895
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4035
_exptl_absorpt_correction_T_max  0.6044
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12442
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_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         2.049
_diffrn_reflns_theta_max         28.051
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3433
_reflns_number_gt                1814
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0099(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3433
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_restrained_S_all      0.870
_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
Br1 Br 0.11528(7) 0.67544(4) 0.81563(4) 0.0712(2) Uani 1 1 d . . . . .
O1 O 0.2168(3) 1.1553(2) 0.94365(19) 0.0361(5) Uani 1 1 d . . . . .
N2 N 0.3917(3) 1.2159(2) 0.8518(2) 0.0287(6) Uani 1 1 d . . . . .
C3 C 0.5616(4) 1.2897(3) 0.8725(3) 0.0289(7) Uani 1 1 d . . . . .
C4 C 0.6763(5) 1.1792(3) 0.9648(3) 0.0410(8) Uani 1 1 d . . . . .
H4A H 0.789241 1.221205 0.982049 0.062 Uiso 1 1 calc R U . . .
H4B H 0.574230 1.121045 1.049266 0.062 Uiso 1 1 calc R U . . .
H4C H 0.738190 1.125296 0.921797 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4629(5) 1.3750(3) 0.9376(3) 0.0437(8) Uani 1 1 d . . . . .
H5A H 0.575493 1.421986 0.950169 0.066 Uiso 1 1 calc R U . . .
H5B H 0.383827 1.441041 0.880267 0.066 Uiso 1 1 calc R U . . .
H5C H 0.366177 1.316669 1.024297 0.066 Uiso 1 1 calc R U . . .
C6 C 0.6973(4) 1.3714(3) 0.7265(3) 0.0315(7) Uani 1 1 d . . . . .
C7 C 0.6150(5) 1.5068(3) 0.6467(3) 0.0453(9) Uani 1 1 d . . . . .
H7A H 0.641533 1.569656 0.680085 0.068 Uiso 1 1 calc R U . . .
H7B H 0.689202 1.544638 0.552237 0.068 Uiso 1 1 calc R U . . .
H7C H 0.462152 1.492093 0.657130 0.068 Uiso 1 1 calc R U . . .
C8 C 0.9373(4) 1.3918(3) 0.7114(3) 0.0449(9) Uani 1 1 d . . . . .
H8A H 0.964645 1.449831 0.749870 0.067 Uiso 1 1 calc R U . . .
H8B H 0.988608 1.304477 0.757875 0.067 Uiso 1 1 calc R U . . .
H8C H 1.011684 1.434225 0.616675 0.067 Uiso 1 1 calc R U . . .
N9 N 0.6494(4) 1.2822(2) 0.6680(3) 0.0331(6) Uani 1 1 d . . . . .
O10 O 0.7614(3) 1.2939(2) 0.5556(2) 0.0487(6) Uani 1 1 d . . . . .
C11 C 0.4585(4) 1.2053(3) 0.7381(3) 0.0278(7) Uani 1 1 d . . . . .
C12 C 0.3441(4) 1.1283(3) 0.6960(3) 0.0285(7) Uani 1 1 d . . . . .
C13 C 0.3954(5) 1.1237(3) 0.5722(3) 0.0366(7) Uani 1 1 d . . . . .
H13 H 0.519999 1.169259 0.503134 0.044 Uiso 1 1 calc R U . . .
N14 N 0.2467(4) 1.0477(3) 0.5655(3) 0.0404(7) Uani 1 1 d . . . . .
N15 N 0.0990(3) 1.0027(2) 0.6843(2) 0.0317(6) Uani 1 1 d . . . . .
C16 C -0.0928(4) 0.9168(3) 0.7124(3) 0.0377(8) Uani 1 1 d . . . . .
H16A H -0.183660 0.970259 0.653822 0.045 Uiso 1 1 calc R U . . .
H16B H -0.173357 0.886372 0.805779 0.045 Uiso 1 1 calc R U . . .
C17 C -0.0449(5) 0.7940(3) 0.6914(3) 0.0436(8) Uani 1 1 d . . . . .
H17A H 0.038536 0.823736 0.598692 0.052 Uiso 1 1 calc R U . . .
H17B H -0.179810 0.743584 0.704883 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1507(4) 1.0480(3) 0.7650(3) 0.0298(7) Uani 1 1 d . . . . .
H18 H 0.070655 1.028732 0.851708 0.036 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
Br1 C17 1.945(3) . ?
O1 N2 1.290(3) . ?
N2 C11 1.342(3) . ?
N2 C3 1.495(3) . ?
C3 C5 1.513(4) . ?
C3 C4 1.530(4) . ?
C3 C6 1.541(4) . ?
C6 N9 1.497(4) . ?
C6 C8 1.523(4) . ?
C6 C7 1.531(4) . ?
N9 O10 1.280(3) . ?
N9 C11 1.354(3) . ?
C11 C12 1.435(4) . ?
C12 C18 1.380(4) . ?
C12 C13 1.415(4) . ?
C13 N14 1.321(3) . ?
N14 N15 1.351(3) . ?
N15 C18 1.341(3) . ?
N15 C16 1.448(3) . ?
C16 C17 1.508(4) . ?

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
O1 N2 C11 125.7(2) . . ?
O1 N2 C3 122.0(2) . . ?
C11 N2 C3 111.7(2) . . ?
N2 C3 C5 110.7(2) . . ?
N2 C3 C4 105.6(2) . . ?
C5 C3 C4 110.5(2) . . ?
N2 C3 C6 100.3(2) . . ?
C5 C3 C6 114.9(2) . . ?
C4 C3 C6 113.9(2) . . ?
N9 C6 C8 110.9(2) . . ?
N9 C6 C7 105.4(2) . . ?
C8 C6 C7 110.5(2) . . ?
N9 C6 C3 100.5(2) . . ?
C8 C6 C3 115.0(2) . . ?
C7 C6 C3 113.7(2) . . ?
O10 N9 C11 125.5(2) . . ?
O10 N9 C6 122.9(2) . . ?
C11 N9 C6 110.9(2) . . ?
N2 C11 N9 108.5(2) . . ?
N2 C11 C12 125.8(2) . . ?
N9 C11 C12 125.7(3) . . ?
C18 C12 C13 104.2(2) . . ?
C18 C12 C11 127.3(3) . . ?
C13 C12 C11 128.4(3) . . ?
N14 C13 C12 111.7(3) . . ?
C13 N14 N15 104.5(2) . . ?
C18 N15 N14 112.9(2) . . ?
C18 N15 C16 126.8(3) . . ?
N14 N15 C16 120.2(2) . . ?
N15 C16 C17 112.9(2) . . ?
C16 C17 Br1 111.1(2) . . ?
N15 C18 C12 106.7(3) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_2014s
_database_code_depnum_ccdc_archive 'CCDC 2430095'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C13 H21 N4 O2'
_chemical_formula_weight         265.34

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.2774(4)
_cell_length_b                   13.9041(4)
_cell_length_c                   18.6426(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2923.20(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3306
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      23.38

_exptl_crystal_description       block
_exptl_crystal_colour            dark-blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2344
_exptl_absorpt_correction_T_max  0.2660
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18355
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3618
_reflns_number_gt                1750
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3618
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_restrained_S_all      0.875
_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 0.14168(11) 0.08126(8) 0.59223(6) 0.0662(4) Uani 1 1 d . . . . .
N2 N 0.20283(11) 0.03988(8) 0.54293(6) 0.0474(3) Uani 1 1 d . . . . .
C3 C 0.21770(14) 0.08386(10) 0.46987(8) 0.0473(4) Uani 1 1 d . . . . .
C4 C 0.30423(16) 0.16746(11) 0.47967(10) 0.0666(5) Uani 1 1 d . . . . .
H4A H 0.378507 0.143430 0.497327 0.100 Uiso 1 1 calc R U . . .
H4B H 0.271978 0.212575 0.513425 0.100 Uiso 1 1 calc R U . . .
H4C H 0.316548 0.198882 0.434430 0.100 Uiso 1 1 calc R U . . .
C5 C 0.09898(16) 0.11996(12) 0.44242(10) 0.0692(5) Uani 1 1 d . . . . .
H5A H 0.107145 0.140346 0.393473 0.104 Uiso 1 1 calc R U . . .
H5B H 0.073197 0.173211 0.471247 0.104 Uiso 1 1 calc R U . . .
H5C H 0.041553 0.069126 0.445197 0.104 Uiso 1 1 calc R U . . .
C6 C 0.27070(14) -0.00249(9) 0.42796(8) 0.0464(4) Uani 1 1 d . . . . .
C7 C 0.36928(16) 0.02308(12) 0.37616(9) 0.0668(5) Uani 1 1 d . . . . .
H7A H 0.395502 -0.033935 0.351833 0.100 Uiso 1 1 calc R U . . .
H7B H 0.434394 0.050708 0.402157 0.100 Uiso 1 1 calc R U . . .
H7C H 0.340424 0.068683 0.341657 0.100 Uiso 1 1 calc R U . . .
C8 C 0.17878(17) -0.06529(12) 0.39097(9) 0.0674(5) Uani 1 1 d . . . . .
H8A H 0.145892 -0.031224 0.350846 0.101 Uiso 1 1 calc R U . . .
H8B H 0.116723 -0.080863 0.424257 0.101 Uiso 1 1 calc R U . . .
H8C H 0.215688 -0.123442 0.374470 0.101 Uiso 1 1 calc R U . . .
N9 N 0.32051(11) -0.06094(8) 0.48832(6) 0.0469(3) Uani 1 1 d . . . . .
O10 O 0.39187(10) -0.13100(7) 0.47732(6) 0.0649(4) Uani 1 1 d . . . . .
C11 C 0.27162(13) -0.03808(10) 0.55170(7) 0.0432(4) Uani 1 1 d . . . . .
C12 C 0.29326(13) -0.08720(10) 0.61789(8) 0.0451(4) Uani 1 1 d . . . . .
C13 C 0.26000(16) -0.06018(11) 0.68750(8) 0.0579(4) Uani 1 1 d . . . . .
H13 H 0.215402 -0.005691 0.697956 0.070 Uiso 1 1 calc R U . . .
N14 N 0.29919(14) -0.12088(9) 0.73647(7) 0.0647(4) Uani 1 1 d . . . . .
N15 N 0.35712(12) -0.18962(8) 0.69846(7) 0.0542(4) Uani 1 1 d . . . . .
C16 C 0.41383(16) -0.26907(11) 0.73629(9) 0.0623(5) Uani 1 1 d . . . . .
H16A H 0.418593 -0.324038 0.704374 0.075 Uiso 1 1 calc R U . . .
H16B H 0.364878 -0.287223 0.776871 0.075 Uiso 1 1 calc R U . . .
C17 C 0.53511(16) -0.24537(11) 0.76247(9) 0.0699(5) Uani 1 1 d . . . . .
H17A H 0.532309 -0.185685 0.789365 0.084 Uiso 1 1 calc R U . . .
H17B H 0.587135 -0.235759 0.721661 0.084 Uiso 1 1 calc R U . . .
C18 C 0.58544(17) -0.32387(13) 0.80968(11) 0.0876(6) Uani 1 1 d . . . . .
H18A H 0.586124 -0.383513 0.783748 0.131 Uiso 1 1 calc R U . . .
H18B H 0.537223 -0.330533 0.851828 0.131 Uiso 1 1 calc R U . . .
H18C H 0.664916 -0.307377 0.823434 0.131 Uiso 1 1 calc R U . . .
C19 C 0.35623(14) -0.17164(10) 0.62809(8) 0.0498(4) Uani 1 1 d . . . . .
H19 H 0.391362 -0.208900 0.592525 0.060 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 N2 1.2851(14) . ?
N2 C11 1.3429(18) . ?
N2 C3 1.5024(19) . ?
C3 C5 1.519(2) . ?
C3 C4 1.529(2) . ?
C3 C6 1.5522(19) . ?
C6 N9 1.4973(18) . ?
C6 C7 1.515(2) . ?
C6 C8 1.521(2) . ?
N9 O10 1.2801(14) . ?
N9 C11 1.3421(17) . ?
C11 C12 1.431(2) . ?
C12 C19 1.385(2) . ?
C12 C13 1.402(2) . ?
C13 N14 1.3196(19) . ?
N14 N15 1.3572(17) . ?
N15 C19 1.3357(18) . ?
N15 C16 1.4583(18) . ?
C16 C17 1.489(2) . ?
C17 C18 1.513(2) . ?

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
O1 N2 C11 125.75(12) . . ?
O1 N2 C3 121.74(11) . . ?
C11 N2 C3 111.99(11) . . ?
N2 C3 C5 109.97(13) . . ?
N2 C3 C4 105.80(12) . . ?
C5 C3 C4 110.60(13) . . ?
N2 C3 C6 100.63(10) . . ?
C5 C3 C6 115.19(13) . . ?
C4 C3 C6 113.74(13) . . ?
N9 C6 C7 109.34(12) . . ?
N9 C6 C8 106.55(11) . . ?
C7 C6 C8 110.24(13) . . ?
N9 C6 C3 100.72(11) . . ?
C7 C6 C3 114.96(12) . . ?
C8 C6 C3 114.20(13) . . ?
O10 N9 C11 125.41(12) . . ?
O10 N9 C6 121.91(11) . . ?
C11 N9 C6 112.27(12) . . ?
N9 C11 N2 108.74(12) . . ?
N9 C11 C12 125.17(13) . . ?
N2 C11 C12 126.05(13) . . ?
C19 C12 C13 103.73(13) . . ?
C19 C12 C11 127.59(13) . . ?
C13 C12 C11 128.64(14) . . ?
N14 C13 C12 112.29(14) . . ?
C13 N14 N15 104.50(13) . . ?
C19 N15 N14 112.17(12) . . ?
C19 N15 C16 128.32(14) . . ?
N14 N15 C16 119.48(13) . . ?
N15 C16 C17 113.18(13) . . ?
C16 C17 C18 112.06(14) . . ?
N15 C19 C12 107.29(13) . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_RsecBUs
_database_code_depnum_ccdc_archive 'CCDC 2430096'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C14 H23 N4 O2'
_chemical_formula_weight         279.36

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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3953(2)
_cell_length_b                   12.4423(4)
_cell_length_c                   17.4655(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.508(2)
_cell_angle_gamma                90
_cell_volume                     1589.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3259
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      21.96

_exptl_crystal_description       bulk
_exptl_crystal_colour            dark_blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2420
_exptl_absorpt_correction_T_max  0.2966
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15241
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.017
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3931
_reflns_number_gt                1619
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0977P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3931
_refine_ls_number_parameters     219
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1919
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.919
_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 0.2095(2) 0.52954(11) 0.44040(9) 0.0796(5) Uani 1 1 d . . . . .
N2 N 0.2916(2) 0.48474(12) 0.38908(8) 0.0568(5) Uani 1 1 d . . . . .
C3 C 0.3965(3) 0.54803(16) 0.33784(11) 0.0635(6) Uani 1 1 d . . . . .
C4 C 0.2536(4) 0.6057(2) 0.27970(14) 0.0966(8) Uani 1 1 d . . . . .
H4A H 0.314055 0.647877 0.245075 0.145 Uiso 1 1 calc R U . . .
H4B H 0.176165 0.553483 0.250590 0.145 Uiso 1 1 calc R U . . .
H4C H 0.180821 0.651796 0.306984 0.145 Uiso 1 1 calc R U . . .
C5 C 0.5174(3) 0.62931(19) 0.38465(14) 0.0941(8) Uani 1 1 d . . . . .
H5A H 0.584013 0.669383 0.351023 0.141 Uiso 1 1 calc R U . . .
H5B H 0.443353 0.677482 0.409692 0.141 Uiso 1 1 calc R U . . .
H5C H 0.601847 0.592795 0.423020 0.141 Uiso 1 1 calc R U . . .
C6 C 0.4984(3) 0.45703(17) 0.30152(12) 0.0663(6) Uani 1 1 d . . . . .
C7 C 0.5103(4) 0.4693(2) 0.21585(14) 0.1048(9) Uani 1 1 d . . . . .
H7A H 0.586568 0.529641 0.208353 0.157 Uiso 1 1 calc R U . . .
H7B H 0.561651 0.405218 0.197250 0.157 Uiso 1 1 calc R U . . .
H7C H 0.390046 0.480690 0.187806 0.157 Uiso 1 1 calc R U . . .
C8 C 0.6867(3) 0.4315(2) 0.34650(16) 0.1000(9) Uani 1 1 d . . . . .
H8A H 0.768847 0.489755 0.341018 0.150 Uiso 1 1 calc R U . . .
H8B H 0.676782 0.421788 0.400256 0.150 Uiso 1 1 calc R U . . .
H8C H 0.732806 0.366750 0.326508 0.150 Uiso 1 1 calc R U . . .
N9 N 0.3795(2) 0.36294(13) 0.31296(9) 0.0628(5) Uani 1 1 d . . . . .
O10 O 0.3964(2) 0.27219(13) 0.27985(9) 0.0892(6) Uani 1 1 d . . . . .
C11 C 0.2738(2) 0.38111(15) 0.36815(10) 0.0527(5) Uani 1 1 d . . . . .
C12 C 0.1618(3) 0.30344(15) 0.39916(12) 0.0570(5) Uani 1 1 d . . . . .
C13 C 0.1330(4) 0.19481(19) 0.37750(16) 0.0876(8) Uani 1 1 d . . . . .
H13 H 0.186(3) 0.157(2) 0.3356(14) 0.105 Uiso 1 1 d . U . . .
N14 N 0.0062(8) 0.1480(4) 0.4090(3) 0.0714(12) Uani 0.671(6) 1 d . . P A 1
N15 N -0.0406(9) 0.2247(6) 0.4578(3) 0.0607(12) Uani 0.671(6) 1 d . . P A 1
C16 C -0.1728(8) 0.2019(5) 0.5111(3) 0.0763(15) Uani 0.671(6) 1 d . . P A 1
H16 H -0.205052 0.270656 0.532832 0.092 Uiso 0.671(6) 1 calc R U P A 1
C17 C -0.3460(13) 0.1582(11) 0.4610(8) 0.111(2) Uani 0.671(6) 1 d . U P A 1
H17A H -0.386948 0.208573 0.420460 0.167 Uiso 0.671(6) 1 calc R U P A 1
H17B H -0.318841 0.090702 0.438587 0.167 Uiso 0.671(6) 1 calc R U P A 1
H17C H -0.440333 0.148066 0.492606 0.167 Uiso 0.671(6) 1 calc R U P A 1
C18 C -0.0941(10) 0.1349(5) 0.5748(4) 0.125(3) Uani 0.671(6) 1 d . U P A 1
H18A H -0.179515 0.131520 0.611920 0.150 Uiso 0.671(6) 1 calc R U P A 1
H18B H -0.081861 0.062656 0.555351 0.150 Uiso 0.671(6) 1 calc R U P A 1
C19 C 0.0615(19) 0.1642(11) 0.6107(5) 0.141(3) Uani 0.671(6) 1 d . . P A 1
H19A H 0.100913 0.114365 0.651782 0.211 Uiso 0.671(6) 1 calc R U P A 1
H19B H 0.149126 0.165617 0.575330 0.211 Uiso 0.671(6) 1 calc R U P A 1
H19C H 0.051180 0.234687 0.632068 0.211 Uiso 0.671(6) 1 calc R U P A 1
N14B N 0.0559(17) 0.1448(10) 0.4417(6) 0.0714(12) Uani 0.329(6) 1 d . . P A 2
N15B N 0.005(2) 0.2238(13) 0.4840(7) 0.0607(12) Uani 0.329(6) 1 d . . P A 2
C16B C -0.0959(13) 0.1944(8) 0.5476(7) 0.056(2) Uani 0.329(6) 1 d . . P A 2
H16B H -0.152761 0.261355 0.561455 0.067 Uiso 0.329(6) 1 calc R U P A 2
C17B C -0.402(3) 0.150(2) 0.4679(18) 0.111(2) Uani 0.329(6) 1 d . . P A 2
H17D H -0.486180 0.091119 0.457293 0.167 Uiso 0.329(6) 1 calc R U P A 2
H17E H -0.461342 0.208644 0.489485 0.167 Uiso 0.329(6) 1 calc R U P A 2
H17F H -0.361360 0.172365 0.420678 0.167 Uiso 0.329(6) 1 calc R U P A 2
C18B C -0.2593(10) 0.1183(6) 0.5178(4) 0.064(2) Uani 0.329(6) 1 d . U P A 2
H18C H -0.207831 0.056430 0.495015 0.076 Uiso 0.329(6) 1 calc R U P A 2
H18D H -0.307017 0.092421 0.563274 0.076 Uiso 0.329(6) 1 calc R U P A 2
C19B C 0.033(4) 0.147(2) 0.6356(11) 0.141(3) Uani 0.329(6) 1 d . U P A 2
H19D H -0.048951 0.131057 0.671977 0.211 Uiso 0.329(6) 1 calc R U P A 2
H19E H 0.098668 0.083771 0.625543 0.211 Uiso 0.329(6) 1 calc R U P A 2
H19F H 0.117232 0.202010 0.656722 0.211 Uiso 0.329(6) 1 calc R U P A 2
C20 C 0.0545(3) 0.31811(17) 0.45593(13) 0.0617(6) Uani 1 1 d . . . . .
H20 H 0.040(3) 0.3772(17) 0.4878(11) 0.074 Uiso 1 1 d . 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 N2 1.2820(18) . ?
N2 C11 1.341(2) . ?
N2 C3 1.493(2) . ?
C3 C5 1.508(3) . ?
C3 C4 1.532(3) . ?
C3 C6 1.547(3) . ?
C6 N9 1.495(3) . ?
C6 C7 1.519(3) . ?
C6 C8 1.528(3) . ?
N9 O10 1.283(2) . ?
N9 C11 1.347(2) . ?
C11 C12 1.430(3) . ?
C12 C20 1.370(3) . ?
C12 C13 1.411(3) . ?
C13 N14 1.294(6) . ?
C13 N14B 1.470(12) . ?
N14 N15 1.359(9) . ?
N15 C20 1.361(7) . ?
N15 C16 1.473(8) . ?
C16 C18 1.443(8) . ?
C16 C17 1.540(14) . ?
C18 C19 1.280(15) . ?
N14B N15B 1.32(2) . ?
N15B C20 1.343(16) . ?
N15B C16B 1.473(18) . ?
C16B C18B 1.562(14) . ?
C16B C19B 1.78(2) . ?
C17B C18B 1.32(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
O1 N2 C11 124.82(15) . . ?
O1 N2 C3 122.11(15) . . ?
C11 N2 C3 112.49(15) . . ?
N2 C3 C5 110.35(16) . . ?
N2 C3 C4 105.98(17) . . ?
C5 C3 C4 109.95(19) . . ?
N2 C3 C6 100.81(15) . . ?
C5 C3 C6 115.30(18) . . ?
C4 C3 C6 113.66(17) . . ?
N9 C6 C7 109.32(19) . . ?
N9 C6 C8 106.12(17) . . ?
C7 C6 C8 110.3(2) . . ?
N9 C6 C3 100.74(15) . . ?
C7 C6 C3 115.65(19) . . ?
C8 C6 C3 113.81(18) . . ?
O10 N9 C11 125.17(17) . . ?
O10 N9 C6 122.01(17) . . ?
C11 N9 C6 112.29(16) . . ?
N2 C11 N9 108.20(17) . . ?
N2 C11 C12 125.83(17) . . ?
N9 C11 C12 125.97(18) . . ?
C20 C12 C13 103.95(19) . . ?
C20 C12 C11 127.84(18) . . ?
C13 C12 C11 128.20(19) . . ?
N14 C13 C12 114.0(3) . . ?
C12 C13 N14B 105.1(5) . . ?
C13 N14 N15 102.6(5) . . ?
N14 N15 C20 113.8(5) . . ?
N14 N15 C16 121.0(6) . . ?
C20 N15 C16 125.0(5) . . ?
C18 C16 N15 111.7(5) . . ?
C18 C16 C17 116.2(7) . . ?
N15 C16 C17 106.5(5) . . ?
C19 C18 C16 116.4(8) . . ?
N15B N14B C13 106.7(10) . . ?
N14B N15B C20 109.3(12) . . ?
N14B N15B C16B 117.1(13) . . ?
C20 N15B C16B 133.5(13) . . ?
N15B C16B C18B 110.7(9) . . ?
N15B C16B C19B 117.8(12) . . ?
C18B C16B C19B 112.1(12) . . ?
C17B C18B C16B 122.7(13) . . ?
N15B C20 C12 111.5(7) . . ?
N15 C20 C12 105.1(3) . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_2088
_database_code_depnum_ccdc_archive 'CCDC 2430090'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C13 H19 N4 O2'
_chemical_formula_weight         263.32

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   11.4485(5)
_cell_length_b                   16.5913(8)
_cell_length_c                   14.7557(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2802.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1473
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      19.38

_exptl_crystal_description       bulk
_exptl_crystal_colour            dark-blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12742
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2859
_reflns_number_gt                1285
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0415P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2859
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_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 0.71359(14) 0.43494(10) 0.14133(11) 0.0831(5) Uani 1 1 d . . . . .
N2 N 0.77845(16) 0.37172(11) 0.13814(11) 0.0586(5) Uani 1 1 d . . . . .
C3 C 0.73012(17) 0.28883(14) 0.15200(14) 0.0571(6) Uani 1 1 d . . . . .
C4 C 0.7031(2) 0.28153(15) 0.25363(16) 0.0814(8) Uani 1 1 d . . . . .
H4A H 0.651936 0.324507 0.271555 0.122 Uiso 1 1 calc R U . . .
H4B H 0.774499 0.284849 0.287564 0.122 Uiso 1 1 calc R U . . .
H4C H 0.666030 0.230686 0.265295 0.122 Uiso 1 1 calc R U . . .
C5 C 0.61823(19) 0.27954(16) 0.09802(16) 0.0839(8) Uani 1 1 d . . . . .
H5A H 0.633432 0.290849 0.035313 0.126 Uiso 1 1 calc R U . . .
H5B H 0.560644 0.316522 0.120546 0.126 Uiso 1 1 calc R U . . .
H5C H 0.589779 0.225376 0.104019 0.126 Uiso 1 1 calc R U . . .
C6 C 0.83430(17) 0.23676(13) 0.11984(14) 0.0556(6) Uani 1 1 d . . . . .
C7 C 0.8289(2) 0.21394(15) 0.01947(15) 0.0826(8) Uani 1 1 d . . . . .
H7A H 0.817615 0.261648 -0.016286 0.124 Uiso 1 1 calc R U . . .
H7B H 0.764950 0.177525 0.009618 0.124 Uiso 1 1 calc R U . . .
H7C H 0.900642 0.188311 0.002099 0.124 Uiso 1 1 calc R U . . .
C8 C 0.86082(19) 0.16290(14) 0.17689(17) 0.0800(8) Uani 1 1 d . . . . .
H8A H 0.794045 0.127898 0.177375 0.120 Uiso 1 1 calc R U . . .
H8B H 0.878653 0.179244 0.237748 0.120 Uiso 1 1 calc R U . . .
H8C H 0.926523 0.134824 0.151647 0.120 Uiso 1 1 calc R U . . .
N9 N 0.93226(15) 0.29533(11) 0.12855(10) 0.0531(5) Uani 1 1 d . . . . .
O10 O 1.03977(12) 0.27368(8) 0.12284(10) 0.0686(5) Uani 1 1 d . . . . .
C11 C 0.89551(19) 0.37203(13) 0.13111(13) 0.0498(5) Uani 1 1 d . . . . .
C12 C 0.9683(2) 0.44247(12) 0.12698(12) 0.0510(5) Uani 1 1 d . . . . .
C13 C 0.9364(2) 0.52415(16) 0.12854(15) 0.0806(8) Uani 1 1 d . . . . .
H13 H 0.859637 0.541959 0.133143 0.097 Uiso 1 1 calc R U . . .
N14 N 1.0271(2) 0.57299(12) 0.12278(14) 0.0841(7) Uani 1 1 d . . . . .
N15 N 1.11865(18) 0.52315(12) 0.11712(11) 0.0638(5) Uani 1 1 d . . . . .
C16A C 1.2348(3) 0.55754(17) 0.1075(2) 0.0944(9) Uani 0.662(7) 1 d . . P A 1
H16A H 1.250620 0.565221 0.043500 0.113 Uiso 0.662(7) 1 calc R U P A 1
H16B H 1.235315 0.610275 0.135883 0.113 Uiso 0.662(7) 1 calc R U P A 1
C17A C 1.3273(6) 0.5106(3) 0.1456(5) 0.0782(15) Uani 0.662(7) 1 d . . P A 1
H17A H 1.320518 0.497159 0.206604 0.094 Uiso 0.662(7) 1 calc R U P A 1
C18A C 1.4153(18) 0.4862(17) 0.1057(16) 0.129(3) Uani 0.662(7) 1 d . . P A 1
H18A H 1.426047 0.498077 0.044698 0.155 Uiso 0.662(7) 1 calc R U P A 1
H18B H 1.470766 0.455887 0.136692 0.155 Uiso 0.662(7) 1 calc R U P A 1
C16B C 1.2348(3) 0.55754(17) 0.1075(2) 0.0944(9) Uani 0.338(7) 1 d . . P A 2
H16C H 1.229816 0.599015 0.061339 0.113 Uiso 0.338(7) 1 calc R U P A 2
H16D H 1.252893 0.584614 0.164060 0.113 Uiso 0.338(7) 1 calc R U P A 2
C17B C 1.3282(12) 0.5107(7) 0.0866(9) 0.0782(15) Uani 0.338(7) 1 d D . P A 2
H17B H 1.324349 0.496350 0.025739 0.094 Uiso 0.338(7) 1 calc R U P A 2
C18B C 1.425(4) 0.478(4) 0.124(3) 0.129(3) Uani 0.338(7) 1 d D . P A 2
H18C H 1.441649 0.486634 0.184706 0.155 Uiso 0.338(7) 1 calc R U P A 2
H18D H 1.474644 0.446612 0.088598 0.155 Uiso 0.338(7) 1 calc R U P A 2
C19 C 1.0874(2) 0.44565(13) 0.11925(13) 0.0573(6) Uani 1 1 d . . . . .
H19 H 1.137521 0.401651 0.116052 0.069 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 N2 1.286(2) . ?
N2 C11 1.344(2) . ?
N2 C3 1.496(3) . ?
C3 C5 1.516(3) . ?
C3 C4 1.536(3) . ?
C3 C6 1.547(3) . ?
C6 N9 1.490(2) . ?
C6 C8 1.518(3) . ?
C6 C7 1.530(3) . ?
N9 O10 1.2849(18) . ?
N9 C11 1.341(2) . ?
C11 C12 1.437(3) . ?
C12 C19 1.369(3) . ?
C12 C13 1.404(3) . ?
C13 N14 1.319(3) . ?
N14 N15 1.338(3) . ?
N15 C19 1.335(3) . ?
N15 C16A 1.454(3) . ?
N15 C16B 1.454(3) . ?
C16A C17A 1.429(7) . ?
C17A C18A 1.24(2) . ?
C16B C17B 1.357(14) . ?
C17B C18B 1.35(2) . ?

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
O1 N2 C11 125.13(19) . . ?
O1 N2 C3 122.08(17) . . ?
C11 N2 C3 112.50(18) . . ?
N2 C3 C5 109.51(18) . . ?
N2 C3 C4 106.28(18) . . ?
C5 C3 C4 109.56(18) . . ?
N2 C3 C6 100.73(16) . . ?
C5 C3 C6 115.68(18) . . ?
C4 C3 C6 114.25(18) . . ?
N9 C6 C8 109.17(17) . . ?
N9 C6 C7 106.00(17) . . ?
C8 C6 C7 110.20(19) . . ?
N9 C6 C3 100.93(16) . . ?
C8 C6 C3 115.78(19) . . ?
C7 C6 C3 113.82(17) . . ?
O10 N9 C11 124.60(18) . . ?
O10 N9 C6 122.22(17) . . ?
C11 N9 C6 112.66(17) . . ?
N9 C11 N2 108.15(19) . . ?
N9 C11 C12 126.1(2) . . ?
N2 C11 C12 125.8(2) . . ?
C19 C12 C13 102.9(2) . . ?
C19 C12 C11 127.8(2) . . ?
C13 C12 C11 129.4(2) . . ?
N14 C13 C12 112.8(2) . . ?
C13 N14 N15 103.94(19) . . ?
C19 N15 N14 112.6(2) . . ?
C19 N15 C16A 128.7(2) . . ?
N14 N15 C16A 118.7(2) . . ?
C19 N15 C16B 128.7(2) . . ?
N14 N15 C16B 118.7(2) . . ?
C17A C16A N15 115.2(3) . . ?
C18A C17A C16A 126.5(11) . . ?
C17B C16B N15 121.2(5) . . ?
C18B C17B C16B 142(3) . . ?
N15 C19 C12 107.8(2) . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_2205s
_database_code_depnum_ccdc_archive 'CCDC 2430094'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C14 H23 N4 O2'
_chemical_formula_weight         279.36

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                   13.9705(16)
_cell_length_b                   7.5726(10)
_cell_length_c                   15.0705(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.979(9)
_cell_angle_gamma                90
_cell_volume                     1590.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1678
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      19.19

_exptl_crystal_description       block
_exptl_crystal_colour            dark_blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2315
_exptl_absorpt_correction_T_max  0.2761
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13434
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.923
_diffrn_reflns_theta_max         26.369
_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             3257
_reflns_number_gt                1389
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0431P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0124(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_restrained_S_all      0.822
_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 0.13114(11) -0.01532(17) 0.84749(8) 0.0886(5) Uani 1 1 d . . . . .
N2 N 0.12399(10) 0.1484(2) 0.86807(10) 0.0653(4) Uani 1 1 d . . . . .
C3 C 0.06068(14) 0.2733(2) 0.81404(12) 0.0645(5) Uani 1 1 d . . . . .
C4 C 0.0732(2) 0.2453(3) 0.71560(15) 0.0941(8) Uani 1 1 d . . . . .
H4A H 0.0592(17) 0.120(3) 0.7005(15) 0.141 Uiso 1 1 d . U . . .
H4B H 0.1405(19) 0.269(3) 0.7038(16) 0.141 Uiso 1 1 d . U . . .
H4C H 0.0288(16) 0.333(3) 0.6804(15) 0.141 Uiso 1 1 d . U . . .
C5 C -0.04218(18) 0.2264(4) 0.83518(19) 0.0930(7) Uani 1 1 d . . . . .
H5A H -0.0494(17) 0.095(3) 0.8216(16) 0.139 Uiso 1 1 d . U . . .
H5B H -0.0546(17) 0.250(3) 0.9022(17) 0.139 Uiso 1 1 d . U . . .
H5C H -0.0869(17) 0.298(3) 0.8012(16) 0.139 Uiso 1 1 d . U . . .
C6 C 0.09679(14) 0.4531(2) 0.85262(12) 0.0639(5) Uani 1 1 d . . . . .
C7 C 0.1771(2) 0.5368(3) 0.80365(17) 0.0930(8) Uani 1 1 d . . . . .
H7A H 0.2321(18) 0.445(3) 0.7955(15) 0.139 Uiso 1 1 d . U . . .
H7B H 0.2054(17) 0.631(3) 0.8428(15) 0.139 Uiso 1 1 d . U . . .
H7C H 0.1517(18) 0.576(3) 0.7442(16) 0.139 Uiso 1 1 d . U . . .
C8 C 0.01820(19) 0.5876(3) 0.86745(17) 0.0860(7) Uani 1 1 d . . . . .
H8A H -0.0146(17) 0.616(3) 0.8091(15) 0.129 Uiso 1 1 d . U . . .
H8B H 0.0448(17) 0.693(3) 0.8917(15) 0.129 Uiso 1 1 d . U . . .
H8C H -0.0301(17) 0.541(3) 0.9089(16) 0.129 Uiso 1 1 d . U . . .
N9 N 0.14104(10) 0.3953(2) 0.94121(10) 0.0639(4) Uani 1 1 d . . . . .
O10 O 0.16781(10) 0.50821(16) 1.00173(9) 0.0861(5) Uani 1 1 d . . . . .
C11 C 0.15887(12) 0.2217(2) 0.94522(12) 0.0588(5) Uani 1 1 d . . . . .
C12 C 0.20612(12) 0.1288(2) 1.01802(12) 0.0607(5) Uani 1 1 d . . . . .
C13 C 0.24376(16) 0.1964(3) 1.10011(14) 0.0800(6) Uani 1 1 d . . . . .
H13 H 0.2413(15) 0.328(3) 1.1160(13) 0.120 Uiso 1 1 d . U . . .
N14 N 0.28160(13) 0.0699(3) 1.15248(11) 0.0868(6) Uani 1 1 d . . . . .
N15 N 0.26818(11) -0.0808(2) 1.10435(11) 0.0714(5) Uani 1 1 d . . . . .
C16 C 0.3060(2) -0.2489(3) 1.13973(17) 0.0849(7) Uani 1 1 d . . . . .
H16A H 0.3035(17) -0.242(3) 1.2027(16) 0.127 Uiso 1 1 d . U . . .
H16B H 0.2604(16) -0.342(3) 1.1145(14) 0.127 Uiso 1 1 d . U . . .
C20 C 0.22385(14) -0.0507(3) 1.02441(13) 0.0657(6) Uani 1 1 d . . . . .
H20 H 0.2083(13) -0.145(3) 0.9816(12) 0.099 Uiso 1 1 d . U . . .
C17A C 0.4131(6) -0.2500(10) 1.1401(4) 0.082(2) Uani 0.5 1 d . . P A 1
H17A H 0.437869 -0.353133 1.172229 0.098 Uiso 0.5 1 calc R U P A 1
H17B H 0.438422 -0.146046 1.171230 0.098 Uiso 0.5 1 calc R U P A 1
C18A C 0.4491(6) -0.2523(11) 1.0427(4) 0.091(2) Uani 0.5 1 d . . P A 1
H18A H 0.422893 -0.353498 1.009942 0.109 Uiso 0.5 1 calc R U P A 1
H18B H 0.428845 -0.145763 1.010954 0.109 Uiso 0.5 1 calc R U P A 1
C19A C 0.5594(2) -0.2630(4) 1.0527(2) 0.1520(12) Uani 0.5 1 d . . P A 1
H19A H 0.584154 -0.264683 0.994905 0.228 Uiso 0.5 1 calc R U P A 1
H19B H 0.584311 -0.162125 1.085276 0.228 Uiso 0.5 1 calc R U P A 1
H19C H 0.578388 -0.368854 1.084269 0.228 Uiso 0.5 1 calc R U P A 1
C17B C 0.3908(6) -0.3207(9) 1.0962(7) 0.111(2) Uani 0.5 1 d . . P A 2
H17C H 0.410147 -0.430127 1.125767 0.133 Uiso 0.5 1 calc R U P A 2
H17D H 0.370823 -0.349243 1.034993 0.133 Uiso 0.5 1 calc R U P A 2
C18B C 0.4705(7) -0.2107(11) 1.0965(9) 0.137(3) Uani 0.5 1 d . . P A 2
H18C H 0.489841 -0.185425 1.158215 0.165 Uiso 0.5 1 calc R U P A 2
H18D H 0.448814 -0.099949 1.069675 0.165 Uiso 0.5 1 calc R U P A 2
C19B C 0.5594(2) -0.2630(4) 1.0527(2) 0.1520(12) Uani 0.5 1 d . . P A 2
H19D H 0.606050 -0.170159 1.059993 0.228 Uiso 0.5 1 calc R U P A 2
H19E H 0.585149 -0.369212 1.079700 0.228 Uiso 0.5 1 calc R U P A 2
H19F H 0.543820 -0.283107 0.990508 0.228 Uiso 0.5 1 calc R U 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
O1 N2 1.2836(17) . ?
N2 C11 1.349(2) . ?
N2 C3 1.497(2) . ?
C3 C4 1.521(3) . ?
C3 C5 1.535(3) . ?
C3 C6 1.551(2) . ?
C6 N9 1.497(2) . ?
C6 C7 1.523(3) . ?
C6 C8 1.525(3) . ?
N9 O10 1.2869(16) . ?
N9 C11 1.338(2) . ?
C11 C12 1.426(2) . ?
C12 C20 1.384(2) . ?
C12 C13 1.407(2) . ?
C13 N14 1.327(2) . ?
N14 N15 1.3584(19) . ?
N15 C20 1.336(2) . ?
N15 C16 1.464(2) . ?
C16 C17B 1.496(10) . ?
C16 C17A 1.496(9) . ?
C17A C18A 1.584(10) . ?
C18A C19A 1.540(9) . ?
C17B C18B 1.390(11) . ?
C18B C19B 1.499(10) . ?

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
O1 N2 C11 125.19(16) . . ?
O1 N2 C3 122.13(14) . . ?
C11 N2 C3 111.94(15) . . ?
N2 C3 C4 109.82(16) . . ?
N2 C3 C5 105.51(16) . . ?
C4 C3 C5 110.08(19) . . ?
N2 C3 C6 100.73(14) . . ?
C4 C3 C6 115.55(17) . . ?
C5 C3 C6 114.21(17) . . ?
N9 C6 C7 106.36(17) . . ?
N9 C6 C8 108.76(16) . . ?
C7 C6 C8 110.79(19) . . ?
N9 C6 C3 100.41(13) . . ?
C7 C6 C3 114.52(16) . . ?
C8 C6 C3 114.98(18) . . ?
O10 N9 C11 125.22(16) . . ?
O10 N9 C6 121.27(14) . . ?
C11 N9 C6 113.06(15) . . ?
N9 C11 N2 108.07(16) . . ?
N9 C11 C12 126.44(17) . . ?
N2 C11 C12 125.49(17) . . ?
C20 C12 C13 104.01(18) . . ?
C20 C12 C11 127.52(17) . . ?
C13 C12 C11 128.45(19) . . ?
N14 C13 C12 111.68(19) . . ?
C13 N14 N15 104.73(16) . . ?
C20 N15 N14 112.11(16) . . ?
C20 N15 C16 127.59(18) . . ?
N14 N15 C16 120.19(17) . . ?
N15 C16 C17B 115.7(3) . . ?
N15 C16 C17A 110.0(3) . . ?
N15 C20 C12 107.46(17) . . ?
C16 C17A C18A 112.2(5) . . ?
C19A C18A C17A 106.8(5) . . ?
C18B C17B C16 116.1(9) . . ?
C17B C18B C19B 121.9(9) . . ?

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_1135s
_database_code_depnum_ccdc_archive 'CCDC 2430091'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C14 H21 N4 O2'
_chemical_formula_weight         277.35

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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2645(6)
_cell_length_b                   11.4078(7)
_cell_length_c                   12.3143(6)
_cell_angle_alpha                90
_cell_angle_beta                 118.580(3)
_cell_angle_gamma                90
_cell_volume                     1512.97(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2927
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      23.43

_exptl_crystal_description       bulk
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4815
_exptl_absorpt_correction_T_max  0.5139
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14065
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.891
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3769
_reflns_number_gt                1810
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0629P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3769
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_restrained_S_all      0.891
_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 0.40028(10) 0.43579(11) 0.19730(10) 0.0596(4) Uani 1 1 d . . . . .
N2 N 0.29308(12) 0.39033(12) 0.16382(11) 0.0441(3) Uani 1 1 d . . . . .
C3 C 0.24461(15) 0.29072(15) 0.07435(14) 0.0478(4) Uani 1 1 d . . . . .
C4 C 0.2564(2) 0.3216(3) -0.0396(2) 0.0843(8) Uani 1 1 d . . . . .
H4A H 0.344(2) 0.332(2) -0.015(2) 0.126 Uiso 1 1 d . U . . .
H4B H 0.204(2) 0.400(2) -0.074(2) 0.126 Uiso 1 1 d . U . . .
H4C H 0.219(2) 0.258(2) -0.098(3) 0.126 Uiso 1 1 d . U . . .
C5 C 0.3264(2) 0.1854(2) 0.1415(2) 0.0769(7) Uani 1 1 d . . . . .
H5A H 0.413(2) 0.202(2) 0.164(2) 0.115 Uiso 1 1 d . U . . .
H5B H 0.318(2) 0.164(2) 0.226(2) 0.115 Uiso 1 1 d . U . . .
H5C H 0.298(2) 0.117(2) 0.083(2) 0.115 Uiso 1 1 d . U . . .
C6 C 0.10900(15) 0.27996(15) 0.05230(14) 0.0485(4) Uani 1 1 d . . . . .
C7 C 0.0134(2) 0.3421(3) -0.0645(2) 0.0817(7) Uani 1 1 d . . . . .
H7A H 0.047(2) 0.430(2) -0.062(2) 0.123 Uiso 1 1 d . U . . .
H7B H -0.065(2) 0.343(2) -0.066(2) 0.123 Uiso 1 1 d . U . . .
H7C H 0.007(2) 0.298(2) -0.137(2) 0.123 Uiso 1 1 d . U . . .
C8 C 0.0652(3) 0.1571(2) 0.0586(3) 0.0799(7) Uani 1 1 d . . . . .
H8A H 0.133(2) 0.120(2) 0.141(2) 0.120 Uiso 1 1 d . U . . .
H8B H -0.023(2) 0.164(2) 0.040(2) 0.120 Uiso 1 1 d . U . . .
H8C H 0.067(2) 0.111(2) -0.008(2) 0.120 Uiso 1 1 d . U . . .
N9 N 0.11658(12) 0.34995(12) 0.15877(12) 0.0475(4) Uani 1 1 d . . . . .
O10 O 0.02716(11) 0.35127(12) 0.18502(12) 0.0743(4) Uani 1 1 d . . . . .
C11 C 0.21952(14) 0.41571(14) 0.21379(13) 0.0416(4) Uani 1 1 d . . . . .
C12 C 0.24653(14) 0.49860(14) 0.31088(13) 0.0429(4) Uani 1 1 d . . . . .
C13 C 0.17061(17) 0.53098(17) 0.36298(16) 0.0546(5) Uani 1 1 d . . . . .
H13 H 0.0872(15) 0.5002(16) 0.3401(15) 0.065 Uiso 1 1 d . U . . .
N14 N 0.22546(14) 0.60835(14) 0.45217(13) 0.0605(4) Uani 1 1 d . . . . .
N15 N 0.33733(13) 0.62785(12) 0.45853(12) 0.0528(4) Uani 1 1 d . . . . .
C16 C 0.4179(2) 0.71845(19) 0.54175(18) 0.0704(6) Uani 1 1 d . . . . .
H16A H 0.5036(19) 0.7066(18) 0.5482(17) 0.084 Uiso 1 1 d . U . . .
H16B H 0.4265(18) 0.7031(17) 0.626(2) 0.084 Uiso 1 1 d . U . . .
C17 C 0.3626(3) 0.8398(2) 0.4977(2) 0.0794(7) Uani 1 1 d . . . . .
H17A H 0.419(2) 0.892(2) 0.555(2) 0.095 Uiso 1 1 d . U . . .
H17B H 0.274(2) 0.8423(19) 0.4875(19) 0.095 Uiso 1 1 d . U . . .
C18 C 0.3504(2) 0.87094(19) 0.3748(2) 0.0773(6) Uani 1 1 d . . . . .
H18 H 0.426(2) 0.8828(19) 0.3709(19) 0.093 Uiso 1 1 d . U . . .
C19 C 0.2466(3) 0.8792(2) 0.2746(3) 0.0973(8) Uani 1 1 d . . . . .
H19A H 0.240(2) 0.901(2) 0.190(2) 0.117 Uiso 1 1 d . U . . .
H19B H 0.172(2) 0.866(2) 0.284(2) 0.117 Uiso 1 1 d . U . . .
C20 C 0.35294(17) 0.56387(15) 0.37522(15) 0.0496(4) Uani 1 1 d . . . . .
H20 H 0.4338(14) 0.5694(14) 0.3717(13) 0.060 Uiso 1 1 d . 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 N2 1.2841(15) . ?
N2 C11 1.3445(18) . ?
N2 C3 1.494(2) . ?
C3 C4 1.519(3) . ?
C3 C5 1.530(3) . ?
C3 C6 1.556(2) . ?
C6 N9 1.500(2) . ?
C6 C8 1.516(3) . ?
C6 C7 1.527(3) . ?
N9 O10 1.2832(15) . ?
N9 C11 1.3406(19) . ?
C11 C12 1.433(2) . ?
C12 C20 1.377(2) . ?
C12 C13 1.409(2) . ?
C13 N14 1.316(2) . ?
N14 N15 1.3547(19) . ?
N15 C20 1.345(2) . ?
N15 C16 1.458(2) . ?
C16 C17 1.523(3) . ?
C17 C18 1.490(3) . ?
C18 C19 1.284(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
O1 N2 C11 125.05(13) . . ?
O1 N2 C3 121.94(12) . . ?
C11 N2 C3 112.57(12) . . ?
N2 C3 C4 108.95(15) . . ?
N2 C3 C5 105.81(14) . . ?
C4 C3 C5 110.69(18) . . ?
N2 C3 C6 101.75(12) . . ?
C4 C3 C6 115.04(15) . . ?
C5 C3 C6 113.70(16) . . ?
N9 C6 C8 108.81(15) . . ?
N9 C6 C7 105.98(15) . . ?
C8 C6 C7 110.26(18) . . ?
N9 C6 C3 101.03(12) . . ?
C8 C6 C3 116.05(16) . . ?
C7 C6 C3 113.72(16) . . ?
O10 N9 C11 125.30(13) . . ?
O10 N9 C6 121.57(12) . . ?
C11 N9 C6 112.91(13) . . ?
N9 C11 N2 108.91(13) . . ?
N9 C11 C12 125.22(14) . . ?
N2 C11 C12 125.87(14) . . ?
C20 C12 C13 104.30(15) . . ?
C20 C12 C11 127.87(15) . . ?
C13 C12 C11 127.82(15) . . ?
N14 C13 C12 111.75(16) . . ?
C13 N14 N15 104.92(14) . . ?
C20 N15 N14 112.12(14) . . ?
C20 N15 C16 128.67(17) . . ?
N14 N15 C16 118.94(15) . . ?
N15 C16 C17 110.96(17) . . ?
C18 C17 C16 112.97(19) . . ?
C19 C18 C17 124.5(3) . . ?
N15 C20 C12 106.90(15) . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_1023s
_database_code_depnum_ccdc_archive 'CCDC 2430093'
loop_
_audit_author_name
_audit_author_address
'Gleb Letyagin'
;ITC SB RAS
Russia
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-08 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         ?
_chemical_formula_sum            'C14 H23 N4 O2'
_chemical_formula_weight         279.36

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                   7.5557(3)
_cell_length_b                   21.6258(7)
_cell_length_c                   9.6210(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.616(3)
_cell_angle_gamma                90
_cell_volume                     1564.51(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1206
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      19.54

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2408
_exptl_absorpt_correction_T_max  0.2757
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13634
_diffrn_reflns_av_unetI/netI     0.1081
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.883
_diffrn_reflns_theta_max         26.372
_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             3194
_reflns_number_gt                1311
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0388P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   0.800
_refine_ls_restrained_S_all      0.800
_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 0.5233(2) 0.23736(7) 0.7246(2) 0.0792(6) Uani 1 1 d . . . . .
N2 N 0.6919(2) 0.24415(8) 0.73990(18) 0.0489(5) Uani 1 1 d . . . . .
C3 C 0.8137(3) 0.18969(10) 0.7489(2) 0.0476(6) Uani 1 1 d . . . . .
C4 C 0.7856(3) 0.15695(12) 0.8845(3) 0.0800(8) Uani 1 1 d . . . . .
H4A H 0.662299 0.146298 0.884952 0.120 Uiso 1 1 calc R U . . .
H4B H 0.820314 0.183810 0.961817 0.120 Uiso 1 1 calc R U . . .
H4C H 0.856375 0.120023 0.892484 0.120 Uiso 1 1 calc R U . . .
C5 C 0.7619(3) 0.14705(11) 0.6257(3) 0.0734(8) Uani 1 1 d . . . . .
H5A H 0.769688 0.169207 0.540016 0.110 Uiso 1 1 calc R U . . .
H5B H 0.642204 0.132788 0.629826 0.110 Uiso 1 1 calc R U . . .
H5C H 0.841144 0.112258 0.629445 0.110 Uiso 1 1 calc R U . . .
C6 C 0.9992(3) 0.22160(9) 0.7476(2) 0.0456(6) Uani 1 1 d . . . . .
C7 C 1.1356(3) 0.20313(11) 0.8669(3) 0.0707(8) Uani 1 1 d . . . . .
H7A H 1.154492 0.159266 0.864442 0.106 Uiso 1 1 calc R U . . .
H7B H 1.092775 0.214285 0.954194 0.106 Uiso 1 1 calc R U . . .
H7C H 1.245600 0.224167 0.857355 0.106 Uiso 1 1 calc R U . . .
C8 C 1.0825(3) 0.21661(12) 0.6102(3) 0.0734(8) Uani 1 1 d . . . . .
H8A H 1.000973 0.232331 0.535738 0.110 Uiso 1 1 calc R U . . .
H8B H 1.108520 0.174061 0.592274 0.110 Uiso 1 1 calc R U . . .
H8C H 1.190431 0.240275 0.615917 0.110 Uiso 1 1 calc R U . . .
N9 N 0.9513(2) 0.28802(8) 0.76658(19) 0.0530(5) Uani 1 1 d . . . . .
O10 O 1.0720(2) 0.32999(8) 0.7811(2) 0.0864(6) Uani 1 1 d . . . . .
C11 C 0.7760(3) 0.29811(10) 0.7593(2) 0.0431(5) Uani 1 1 d . . . . .
C12 C 0.6910(3) 0.35683(10) 0.7764(2) 0.0454(6) Uani 1 1 d . . . . .
C13 C 0.7696(3) 0.41392(11) 0.8082(3) 0.0736(8) Uani 1 1 d . . . . .
H13 H 0.891604 0.420740 0.814208 0.088 Uiso 1 1 calc R U . . .
N14 N 0.6519(3) 0.45754(9) 0.8289(2) 0.0766(7) Uani 1 1 d . . . . .
N15 N 0.4933(2) 0.42787(9) 0.80966(19) 0.0561(5) Uani 1 1 d . . . . .
C16 C 0.3300(3) 0.46107(11) 0.8298(3) 0.0636(7) Uani 1 1 d . . . . .
H16A H 0.337409 0.476547 0.924800 0.076 Uiso 1 1 calc R U . . .
H16B H 0.230888 0.432405 0.817929 0.076 Uiso 1 1 calc R U . . .
C17 C 0.2934(3) 0.51433(11) 0.7307(3) 0.0683(7) Uani 1 1 d . . . . .
H17 H 0.396178 0.542161 0.741300 0.082 Uiso 1 1 calc R U . . .
C18 C 0.2682(5) 0.49340(16) 0.5815(3) 0.1217(12) Uani 1 1 d . . . . .
H18A H 0.244767 0.528585 0.521678 0.183 Uiso 1 1 calc R U . . .
H18B H 0.169550 0.465277 0.569228 0.183 Uiso 1 1 calc R U . . .
H18C H 0.373993 0.472930 0.558053 0.183 Uiso 1 1 calc R U . . .
C19 C 0.1319(3) 0.54988(12) 0.7707(3) 0.0970(10) Uani 1 1 d . . . . .
H19A H 0.111144 0.584978 0.710226 0.146 Uiso 1 1 calc R U . . .
H19B H 0.153289 0.563697 0.865705 0.146 Uiso 1 1 calc R U . . .
H19C H 0.029513 0.523374 0.761447 0.146 Uiso 1 1 calc R U . . .
C21 C 0.5111(3) 0.36805(10) 0.7784(2) 0.0494(6) Uani 1 1 d . . . . .
H21 H 0.419705 0.339430 0.761177 0.059 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 N2 1.276(2) . ?
N2 C11 1.333(2) . ?
N2 C3 1.492(2) . ?
C3 C4 1.517(3) . ?
C3 C5 1.523(3) . ?
C3 C6 1.563(3) . ?
C6 N9 1.497(2) . ?
C6 C7 1.519(3) . ?
C6 C8 1.523(3) . ?
N9 O10 1.285(2) . ?
N9 C11 1.338(2) . ?
C11 C12 1.440(3) . ?
C12 C21 1.383(3) . ?
C12 C13 1.391(3) . ?
C13 N14 1.325(3) . ?
N14 N15 1.356(2) . ?
N15 C21 1.338(2) . ?
N15 C16 1.457(3) . ?
C16 C17 1.503(3) . ?
C17 C18 1.500(4) . ?
C17 C19 1.523(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
O1 N2 C11 125.00(18) . . ?
O1 N2 C3 121.24(17) . . ?
C11 N2 C3 113.59(17) . . ?
N2 C3 C4 106.31(17) . . ?
N2 C3 C5 108.85(17) . . ?
C4 C3 C5 109.87(19) . . ?
N2 C3 C6 101.50(16) . . ?
C4 C3 C6 114.43(18) . . ?
C5 C3 C6 115.06(18) . . ?
N9 C6 C7 108.34(17) . . ?
N9 C6 C8 107.41(18) . . ?
C7 C6 C8 109.25(19) . . ?
N9 C6 C3 101.26(15) . . ?
C7 C6 C3 114.87(18) . . ?
C8 C6 C3 114.98(18) . . ?
O10 N9 C11 125.41(18) . . ?
O10 N9 C6 120.92(16) . . ?
C11 N9 C6 113.58(18) . . ?
N2 C11 N9 108.70(19) . . ?
N2 C11 C12 125.19(18) . . ?
N9 C11 C12 126.1(2) . . ?
C21 C12 C13 103.9(2) . . ?
C21 C12 C11 127.3(2) . . ?
C13 C12 C11 128.5(2) . . ?
N14 C13 C12 112.7(2) . . ?
C13 N14 N15 103.87(18) . . ?
C21 N15 N14 112.43(18) . . ?
C21 N15 C16 127.69(19) . . ?
N14 N15 C16 119.83(18) . . ?
N15 C16 C17 113.5(2) . . ?
C18 C17 C16 112.0(2) . . ?
C18 C17 C19 111.4(2) . . ?
C16 C17 C19 109.2(2) . . ?
N15 C21 C12 107.05(19) . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.051

