# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2501469'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H21 N O'
_chemical_formula_weight         219.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.0802(5)
_cell_length_b                   9.3390(4)
_cell_length_c                   9.4648(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.201(7)
_cell_angle_gamma                90
_cell_volume                     665.88(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.9(5)
_cell_measurement_reflns_used    9662
_cell_measurement_theta_min      4.7700
_cell_measurement_theta_max      75.2940

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.525
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.52366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.466
_oxdiff_exptl_absorpt_empirical_full_max 2.076
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      99.9(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12447
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.012
_diffrn_reflns_theta_max         76.876
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2643
_reflns_number_gt                2515
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_max     0.896
_reflns_Friedel_fraction_full    0.986

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0593P)²+0.1510P] 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
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     152
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 -0.3615(3) -0.8440(2) -0.9639(2) 0.0375(5) Uani 1 1 d . . . . .
C17 C -0.7989(4) -0.9593(3) -0.9799(3) 0.0361(6) Uani 1 1 d . . . . .
H17 H -0.8139 -1.0382 -1.0467 0.043 Uiso 1 1 calc R U . . .
C11 C -0.4749(3) -0.9543(3) -0.9474(3) 0.0284(5) Uani 1 1 d . . . . .
H7 H -0.5172 -1.0138 -1.0416 0.034 Uiso 1 1 calc R U . . .
N1 N -0.4491(3) -1.1723(2) -0.7909(3) 0.0299(5) Uani 1 1 d . . . . .
C12 C -0.6339(3) -0.8945(3) -0.9176(3) 0.0276(5) Uani 1 1 d . . . . .
C13 C -0.6137(4) -0.7779(3) -0.8219(3) 0.0345(6) Uani 1 1 d . . . . .
H13 H -0.5019 -0.7314 -0.7799 0.041 Uiso 1 1 calc R U . . .
C14 C -0.7578(5) -0.7294(4) -0.7878(4) 0.0493(8) Uani 1 1 d . . . . .
H14 H -0.7436 -0.6498 -0.7219 0.059 Uiso 1 1 calc R U . . .
C16 C -0.9422(4) -0.9105(4) -0.9459(4) 0.0476(8) Uani 1 1 d . . . . .
H16 H -1.0545 -0.9558 -0.9895 0.057 Uiso 1 1 calc R U . . .
C52 C -0.9189(4) -1.3631(3) -0.6124(3) 0.0389(7) Uani 1 1 d . . . . .
H51C H -1.0175 -1.3169 -0.6926 0.058 Uiso 1 1 calc R U . . .
H51B H -0.9509 -1.3767 -0.5228 0.058 Uiso 1 1 calc R U . . .
H51A H -0.8943 -1.4563 -0.6481 0.058 Uiso 1 1 calc R U . . .
C5 C -0.7542(3) -1.2689(3) -0.5713(3) 0.0301(6) Uani 1 1 d . . . . .
H5 H -0.6528 -1.3216 -0.4958 0.036 Uiso 1 1 calc R U . . .
C51 C -0.7830(5) -1.1308(3) -0.4977(4) 0.0454(7) Uani 1 1 d . . . . .
H52A H -0.8190 -1.1538 -0.4119 0.068 Uiso 1 1 calc R U . . .
H52B H -0.8763 -1.0741 -0.5722 0.068 Uiso 1 1 calc R U . . .
H52C H -0.6724 -1.0756 -0.4617 0.068 Uiso 1 1 calc R U . . .
C10 C -0.3568(3) -1.0451(3) -0.8160(3) 0.0296(6) Uani 1 1 d . . . . .
H9A H -0.2506 -1.0755 -0.8370 0.035 Uiso 1 1 calc R U . . .
H9B H -0.3162 -0.9863 -0.7226 0.035 Uiso 1 1 calc R U . . .
C4 C -0.7072(3) -1.2392(3) -0.7114(3) 0.0308(6) Uani 1 1 d . . . . .
H4A H -0.6987 -1.3317 -0.7595 0.037 Uiso 1 1 calc R U . . .
H4B H -0.8049 -1.1837 -0.7851 0.037 Uiso 1 1 calc R U . . .
C15 C -0.9215(4) -0.7958(4) -0.8486(4) 0.0530(9) Uani 1 1 d . . . . .
H15 H -1.0188 -0.7629 -0.8237 0.064 Uiso 1 1 calc R U . . .
C2 C -0.5359(3) -1.1582(3) -0.6787(3) 0.0293(6) Uani 1 1 d . . . . .
H2 H -0.5298 -1.0614 -0.6319 0.035 Uiso 1 1 calc R U . . .
C3 C -0.3654(4) -1.2356(3) -0.6396(3) 0.0384(7) Uani 1 1 d . . . . .
H3AB H -0.2574 -1.1888 -0.5685 0.046 Uiso 1 1 calc R U . . .
H3A H -0.3674 -1.3412 -0.6310 0.046 Uiso 1 1 calc R U . . .
H1 H -0.429(5) -0.786(5) -1.050(5) 0.066(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.424(3) . ?
C17 C16 1.385(4) . ?
C17 C12 1.386(4) . ?
C11 C12 1.518(3) . ?
C11 C10 1.522(4) . ?
N1 C10 1.466(3) . ?
N1 C3 1.469(3) . ?
N1 C2 1.475(3) . ?
C12 C13 1.388(4) . ?
C13 C14 1.392(4) . ?
C14 C15 1.384(5) . ?
C16 C15 1.383(5) . ?
C52 C5 1.524(4) . ?
C5 C51 1.523(4) . ?
C5 C4 1.531(3) . ?
C4 C2 1.508(3) . ?
C2 C3 1.480(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
C16 C17 C12 120.9(3) . . ?
O1 C11 C12 112.0(2) . . ?
O1 C11 C10 104.7(2) . . ?
C12 C11 C10 112.1(2) . . ?
C10 N1 C3 113.7(2) . . ?
C10 N1 C2 116.50(19) . . ?
C3 N1 C2 60.35(16) . . ?
C17 C12 C13 119.2(2) . . ?
C17 C12 C11 120.6(2) . . ?
C13 C12 C11 120.2(2) . . ?
C12 C13 C14 119.7(3) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C16 C17 120.0(3) . . ?
C51 C5 C52 110.0(2) . . ?
C51 C5 C4 111.7(2) . . ?
C52 C5 C4 110.5(2) . . ?
N1 C10 C11 112.2(2) . . ?
C2 C4 C5 114.2(2) . . ?
C16 C15 C14 119.4(3) . . ?
N1 C2 C3 59.62(16) . . ?
N1 C2 C4 116.6(2) . . ?
C3 C2 C4 120.6(2) . . ?
N1 C3 C2 60.03(16) . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2501477'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 N O'
_chemical_formula_weight         205.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   8.50130(10)
_cell_length_b                   10.51100(10)
_cell_length_c                   13.5927(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1214.61(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(4)
_cell_measurement_reflns_used    10091
_cell_measurement_theta_min      3.1830
_cell_measurement_theta_max      76.0190

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_min  0.56413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.675
_oxdiff_exptl_absorpt_empirical_full_max 1.582
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      100.0(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            11512
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.320
_diffrn_reflns_theta_max         76.170
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2397
_reflns_number_gt                2376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_max     0.911
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0400P)²+0.1983P] 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
_refine_ls_extinction_coef       0.0346(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 956 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2397
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.13408(12) 0.73880(10) 0.43753(8) 0.0226(3) Uani 1 1 d . . . . .
N1 N 0.44659(14) 0.62513(12) 0.43231(9) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.27010(17) 0.80960(13) 0.41114(10) 0.0191(3) Uani 1 1 d . . . . .
H11 H 0.3200 0.8441 0.4722 0.023 Uiso 1 1 calc R U . . .
C10 C 0.38414(17) 0.71770(14) 0.36168(10) 0.0193(3) Uani 1 1 d . . . . .
H10A H 0.3292 0.6721 0.3080 0.023 Uiso 1 1 calc R U . . .
H10B H 0.4722 0.7662 0.3323 0.023 Uiso 1 1 calc R U . . .
C12 C 0.22904(17) 0.91960(14) 0.34329(10) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.50242(18) 0.50404(14) 0.38882(12) 0.0247(3) Uani 1 1 d . . . . .
H3A H 0.5943 0.4621 0.4196 0.030 Uiso 1 1 calc R U . . .
H3B H 0.4952 0.4941 0.3165 0.030 Uiso 1 1 calc R U . . .
C13 C 0.13216(18) 0.89888(15) 0.26198(11) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.0932 0.8158 0.2490 0.029 Uiso 1 1 calc R U . . .
C2 C 0.35357(17) 0.50823(13) 0.44551(10) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.2552 0.5030 0.4054 0.024 Uiso 1 1 calc R U . . .
C14 C 0.09221(19) 0.99859(18) 0.19985(12) 0.0312(4) Uani 1 1 d . . . . .
H14 H 0.0263 0.9835 0.1447 0.037 Uiso 1 1 calc R U . . .
C4 C 0.34213(18) 0.45414(14) 0.54824(11) 0.0228(3) Uani 1 1 d . . . . .
H4 H 0.4493 0.4565 0.5786 0.027 Uiso 1 1 calc R U . . .
C17 C 0.28405(18) 1.04193(15) 0.36120(11) 0.0238(3) Uani 1 1 d . . . . .
H17 H 0.3495 1.0575 0.4166 0.029 Uiso 1 1 calc R U . . .
C41 C 0.2319(2) 0.53289(16) 0.61188(12) 0.0317(4) Uani 1 1 d . . . . .
H4IA H 0.2657 0.6220 0.6111 0.047 Uiso 1 1 calc R U . . .
H41C H 0.2344 0.5008 0.6795 0.047 Uiso 1 1 calc R U . . .
H41B H 0.1246 0.5266 0.5860 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2441(2) 1.14207(16) 0.29865(13) 0.0314(4) Uani 1 1 d . . . . .
H16 H 0.2827 1.2253 0.3113 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1482(2) 1.12014(17) 0.21812(13) 0.0336(4) Uani 1 1 d . . . . .
H15 H 0.1209 1.1882 0.1755 0.040 Uiso 1 1 calc R U . . .
C42 C 0.2894(3) 0.31580(16) 0.54227(14) 0.0398(5) Uani 1 1 d . . . . .
H42A H 0.1870 0.3111 0.5093 0.060 Uiso 1 1 calc R U . . .
H42B H 0.2803 0.2807 0.6088 0.060 Uiso 1 1 calc R U . . .
H43C H 0.3669 0.2666 0.5048 0.060 Uiso 1 1 calc R U . . .
H1 H 0.071(3) 0.791(2) 0.4771(17) 0.050(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.4211(17) . ?
N1 C10 1.4664(18) . ?
N1 C2 1.4722(18) . ?
N1 C3 1.4815(18) . ?
C11 C12 1.5196(19) . ?
C11 C10 1.5249(19) . ?
C12 C17 1.390(2) . ?
C12 C13 1.395(2) . ?
C3 C2 1.482(2) . ?
C13 C14 1.388(2) . ?
C2 C4 1.511(2) . ?
C14 C15 1.386(3) . ?
C4 C41 1.520(2) . ?
C4 C42 1.524(2) . ?
C17 C16 1.395(2) . ?
C16 C15 1.384(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
C10 N1 C2 116.05(11) . . ?
C10 N1 C3 115.14(12) . . ?
C2 N1 C3 60.24(9) . . ?
O1 C11 C12 111.39(12) . . ?
O1 C11 C10 107.27(11) . . ?
C12 C11 C10 111.13(11) . . ?
N1 C10 C11 111.21(11) . . ?
C17 C12 C13 118.80(14) . . ?
C17 C12 C11 121.35(13) . . ?
C13 C12 C11 119.84(13) . . ?
N1 C3 C2 59.57(9) . . ?
C14 C13 C12 120.55(15) . . ?
N1 C2 C3 60.19(9) . . ?
N1 C2 C4 117.47(11) . . ?
C3 C2 C4 121.62(13) . . ?
C15 C14 C13 120.19(15) . . ?
C2 C4 C41 111.14(12) . . ?
C2 C4 C42 109.20(13) . . ?
C41 C4 C42 111.62(15) . . ?
C12 C17 C16 120.62(15) . . ?
C15 C16 C17 119.98(16) . . ?
C16 C15 C14 119.84(15) . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2501474'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N4 O'
_chemical_formula_weight         282.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.8150(2)
_cell_length_b                   6.55570(10)
_cell_length_c                   11.7844(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.377(2)
_cell_angle_gamma                90
_cell_volume                     783.23(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    110.00(10)
_cell_measurement_reflns_used    10525
_cell_measurement_theta_min      3.9670
_cell_measurement_theta_max      75.1480

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.625
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.644
_oxdiff_exptl_absorpt_empirical_full_max 1.284
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14388
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.002
_diffrn_reflns_theta_max         76.393
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.751
_diffrn_reflns_point_group_measured_fraction_full 0.824
_reflns_number_total             2469
_reflns_number_gt                2441
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.471
_reflns_Friedel_fraction_max     0.529
_reflns_Friedel_fraction_full    0.611

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0833P)²+0.2805P] 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
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(17)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2469
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.50160(19) 0.5014(4) 0.38245(16) 0.0293(5) Uani 1 1 d . . . . .
N1 N 0.5184(2) 0.4227(4) 0.61938(19) 0.0261(5) Uani 1 1 d . . . . .
N31 N 0.2616(2) 0.4702(5) 0.6127(2) 0.0381(7) Uani 1 1 d . . . . .
C2 C 0.4906(3) 0.5145(5) 0.7221(2) 0.0277(6) Uani 1 1 d . . . . .
H2B H 0.4826 0.6643 0.7114 0.033 Uiso 1 1 calc R U . . .
H2A H 0.5648 0.4861 0.7982 0.033 Uiso 1 1 calc R U . . .
C10 C 0.6326(3) 0.5172(5) 0.5992(2) 0.0265(6) Uani 1 1 d . . . . .
H10 H 0.6257 0.6687 0.6048 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6274(3) 0.4624(5) 0.4712(2) 0.0285(6) Uani 1 1 d . . . . .
H11A H 0.6949 0.5426 0.4516 0.034 Uiso 1 1 calc R U . . .
H11B H 0.6490 0.3161 0.4688 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7617(3) 0.4479(5) 0.6931(2) 0.0289(6) Uani 1 1 d . . . . .
C3 C 0.3638(3) 0.4291(5) 0.7313(2) 0.0322(6) Uani 1 1 d . . . . .
H3 H 0.3732 0.2784 0.7444 0.039 Uiso 1 1 calc R U . . .
C41 C 0.3351(3) 0.5263(6) 0.8354(3) 0.0370(7) Uani 1 1 d . . . . .
C17 C 0.8395(3) 0.5884(6) 0.7752(3) 0.0376(8) Uani 1 1 d . . . . .
H17 H 0.8108 0.7258 0.7732 0.045 Uiso 1 1 calc R U . . .
C15 C 1.0017(3) 0.3316(7) 0.8643(3) 0.0428(9) Uani 1 1 d . . . . .
H15 H 1.0837 0.2921 0.9227 0.051 Uiso 1 1 calc R U . . .
C46 C 0.2808(3) 0.7195(6) 0.8245(3) 0.0461(8) Uani 1 1 d . . . . .
H46 H 0.2593 0.7911 0.7500 0.055 Uiso 1 1 calc R U . . .
C16 C 0.9596(3) 0.5287(7) 0.8606(3) 0.0468(9) Uani 1 1 d . . . . .
H16 H 1.0124 0.6257 0.9165 0.056 Uiso 1 1 calc R U . . .
N32 N 0.1474(3) 0.4046(8) 0.5967(3) 0.0658(11) Uani 1 1 d . . . . .
C13 C 0.8047(3) 0.2476(5) 0.6983(3) 0.0351(7) Uani 1 1 d . . . . .
H13 H 0.7515 0.1495 0.6435 0.042 Uiso 1 1 calc R U . . .
C14 C 0.9252(3) 0.1890(6) 0.7831(3) 0.0432(8) Uani 1 1 d . . . . .
H14 H 0.9549 0.0522 0.7854 0.052 Uiso 1 1 calc R U . . .
C42 C 0.3696(3) 0.4265(7) 0.9464(3) 0.0455(9) Uani 1 1 d . . . . .
H42 H 0.4095 0.2955 0.9556 0.055 Uiso 1 1 calc R U . . .
C44 C 0.2895(4) 0.7050(10) 1.0305(4) 0.0697(16) Uani 1 1 d . . . . .
H44 H 0.2719 0.7650 1.0967 0.084 Uiso 1 1 calc R U . . .
C45 C 0.2575(4) 0.8097(8) 0.9224(5) 0.0652(14) Uani 1 1 d . . . . .
H45 H 0.2199 0.9422 0.9147 0.078 Uiso 1 1 calc R U . . .
C43 C 0.3465(4) 0.5157(10) 1.0436(3) 0.0632(14) Uani 1 1 d . . . . .
H43 H 0.3699 0.4461 1.1189 0.076 Uiso 1 1 calc R U . . .
N33 N 0.0421(5) 0.3607(14) 0.5667(6) 0.124(3) Uani 1 1 d . . . . .
H1N H 0.451(3) 0.463(6) 0.556(3) 0.034(9) Uiso 1 1 d . . . . .
H1O H 0.494(3) 0.629(6) 0.379(3) 0.018(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.421(3) . ?
O1 H1O 0.84(4) . ?
N1 C10 1.473(3) . ?
N1 C2 1.474(3) . ?
N1 H1N 0.88(4) . ?
N31 N32 1.258(4) . ?
N31 C3 1.474(4) . ?
C2 C3 1.519(4) . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
C10 C12 1.517(4) . ?
C10 C11 1.532(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.388(4) . ?
C12 C13 1.388(5) . ?
C3 C41 1.508(4) . ?
C3 H3 1.0000 . ?
C41 C46 1.383(5) . ?
C41 C42 1.393(5) . ?
C17 C16 1.394(5) . ?
C17 H17 0.9500 . ?
C15 C16 1.366(6) . ?
C15 C14 1.386(5) . ?
C15 H15 0.9500 . ?
C46 C45 1.395(5) . ?
C46 H46 0.9500 . ?
C16 H16 0.9500 . ?
N32 N33 1.107(5) . ?
C13 C14 1.393(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C42 C43 1.384(5) . ?
C42 H42 0.9500 . ?
C44 C43 1.370(8) . ?
C44 C45 1.381(8) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C43 H43 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 H1O 105(2) . . ?
C10 N1 C2 112.5(2) . . ?
C10 N1 H1N 103(2) . . ?
C2 N1 H1N 103(2) . . ?
N32 N31 C3 117.0(3) . . ?
N1 C2 C3 110.8(2) . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
H2B C2 H2A 108.1 . . ?
N1 C10 C12 111.5(2) . . ?
N1 C10 C11 108.3(2) . . ?
C12 C10 C11 110.9(2) . . ?
N1 C10 H10 108.7 . . ?
C12 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
O1 C11 C10 112.4(2) . . ?
O1 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O1 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C17 C12 C13 119.0(3) . . ?
C17 C12 C10 119.3(3) . . ?
C13 C12 C10 121.6(3) . . ?
N31 C3 C41 113.3(3) . . ?
N31 C3 C2 105.3(2) . . ?
C41 C3 C2 110.4(2) . . ?
N31 C3 H3 109.3 . . ?
C41 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C46 C41 C42 119.0(3) . . ?
C46 C41 C3 120.8(3) . . ?
C42 C41 C3 120.2(3) . . ?
C12 C17 C16 120.2(4) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C41 C46 C45 120.3(4) . . ?
C41 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
N33 N32 N31 169.8(6) . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C43 C42 C41 120.8(4) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C43 C44 C45 120.8(3) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C44 C45 C46 119.5(5) . . ?
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C44 C43 C42 119.5(4) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2501478'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 N4 O'
_chemical_formula_weight         350.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.60730(10)
_cell_length_b                   14.1220(2)
_cell_length_c                   24.5457(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1943.68(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294.58(10)
_cell_measurement_reflns_used    13079
_cell_measurement_theta_min      3.1060
_cell_measurement_theta_max      76.4410

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.597
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.64202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.499
_oxdiff_exptl_absorpt_empirical_full_max 1.477
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      294.58(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            18682
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.601
_diffrn_reflns_theta_max         76.761
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3906
_reflns_number_gt                3636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_max     0.920
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0962P)²+0.1011P] 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
_refine_ls_extinction_coef       0.0034(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(11)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3906
_refine_ls_number_parameters     263
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.068
_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 0.6705(3) 0.25243(12) 0.47112(9) 0.0711(5) Uani 1 1 d . . . . .
N1 N 0.4707(3) 0.42022(13) 0.52003(8) 0.0526(4) Uani 1 1 d . . . . .
H1N H 0.380(5) 0.4382(18) 0.4887(10) 0.050(6) Uiso 1 1 d . . . . .
H1O H 0.795(7) 0.218(3) 0.4735(16) 0.097(11) Uiso 1 1 d . . . . .
N2 N 0.3592(3) 0.62211(12) 0.50505(8) 0.0516(4) Uani 1 1 d . . . . .
N3 N 0.1195(3) 0.62135(16) 0.50193(10) 0.0643(5) Uani 1 1 d . . . . .
N4 N 0.0636(3) 0.65388(16) 0.45345(9) 0.0633(5) Uani 1 1 d . . . . .
C7 C 0.4555(4) 0.65577(15) 0.45870(9) 0.0532(5) Uani 1 1 d . . . . .
H7 H 0.6165 0.6636 0.4508 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2661(4) 0.67585(14) 0.42588(9) 0.0516(4) Uani 1 1 d . . . . .
C61 C 0.2610(4) 0.71307(15) 0.37006(9) 0.0565(5) Uani 1 1 d . . . . .
C1 C 0.4153(4) 0.48413(16) 0.56549(9) 0.0562(5) Uani 1 1 d . . . . .
H1 H 0.2420 0.4818 0.5705 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6180(4) 0.38002(17) 0.40680(9) 0.0568(5) Uani 1 1 d . . . . .
C11 C 0.7513(4) 0.34413(16) 0.45656(9) 0.0581(5) Uani 1 1 d . . . . .
H11 H 0.9213 0.3401 0.4475 0.070 Uiso 1 1 calc R U . . .
C2 C 0.4791(4) 0.58818(17) 0.55388(9) 0.0583(5) Uani 1 1 d . . . . .
H2B H 0.4327 0.6270 0.5847 0.070 Uiso 1 1 calc R U . . .
H2A H 0.6503 0.5940 0.5492 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7223(4) 0.41157(18) 0.50454(9) 0.0581(5) Uani 1 1 d . . . . .
H15A H 0.8135 0.3882 0.5353 0.070 Uiso 1 1 calc R U . . .
H10A H 0.7842 0.4734 0.4948 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4124(5) 0.3375(2) 0.38920(12) 0.0739(7) Uani 1 1 d . . . . .
H13 H 0.3562 0.2837 0.4069 0.089 Uiso 1 1 calc R U . . .
C17 C 0.6978(6) 0.4598(2) 0.37902(11) 0.0763(7) Uani 1 1 d . . . . .
H17 H 0.8380 0.4894 0.3899 0.092 Uiso 1 1 calc R U . . .
C62 C 0.0730(5) 0.6936(2) 0.33569(13) 0.0762(7) Uani 1 1 d . . . . .
H52 H -0.0559 0.6587 0.3485 0.091 Uiso 1 1 calc R U . . .
C66 C 0.4476(5) 0.7662(3) 0.34999(13) 0.0806(8) Uani 1 1 d . . . . .
H66 H 0.5754 0.7813 0.3725 0.097 Uiso 1 1 calc R U . . .
C64 C 0.2614(6) 0.7774(3) 0.26274(13) 0.0865(8) Uani 1 1 d . . . . .
H64 H 0.2619 0.7986 0.2269 0.104 Uiso 1 1 calc R U . . .
C65 C 0.4463(6) 0.7973(3) 0.29645(14) 0.0946(10) Uani 1 1 d . . . . .
H65 H 0.5744 0.8325 0.2834 0.113 Uiso 1 1 calc R U . . .
C63 C 0.0738(7) 0.7254(3) 0.28241(14) 0.0884(9) Uani 1 1 d . . . . .
H63 H -0.0542 0.7114 0.2597 0.106 Uiso 1 1 calc R U . . .
C15 C 0.3670(8) 0.4526(3) 0.31860(13) 0.0915(10) Uani 1 1 d . . . . .
H15 H 0.2827 0.4766 0.2891 0.110 Uiso 1 1 calc R U . . .
C14 C 0.2868(6) 0.3743(3) 0.34509(13) 0.0909(9) Uani 1 1 d . . . . .
H14 H 0.1468 0.3451 0.3337 0.109 Uiso 1 1 calc R U . . .
C16 C 0.5709(8) 0.4956(2) 0.33543(13) 0.0910(11) Uani 1 1 d . . . . .
H16 H 0.6253 0.5495 0.3175 0.109 Uiso 1 1 calc R U . . .
C5 C 0.4418(15) 0.5154(4) 0.66749(16) 0.158(3) Uani 1 1 d . . . . .
H5A H 0.5317 0.5000 0.6996 0.237 Uiso 1 1 calc R U . . .
H5B H 0.2755 0.5042 0.6742 0.237 Uiso 1 1 calc R U . . .
H5D H 0.4656 0.5809 0.6585 0.237 Uiso 1 1 calc R U . . .
C3 C 0.5263(7) 0.4529(3) 0.61952(11) 0.0839(9) Uani 1 1 d D . . . .
C4A_a C 0.4862(16) 0.3539(3) 0.6320(2) 0.095(2) Uani 0.692(10) 1 d D . P A 1
H4A1_a H 0.5874 0.3353 0.6617 0.142 Uiso 0.692(10) 1 calc R U P A 1
H4A2_a H 0.5224 0.3162 0.6005 0.142 Uiso 0.692(10) 1 calc R U P A 1
H4A3_a H 0.3224 0.3447 0.6420 0.142 Uiso 0.692(10) 1 calc R U P A 1
C4B_b C 0.760(2) 0.461(2) 0.6346(9) 0.112(5) Uani 0.308(10) 1 d D . P A 2
H4B1_b H 0.7931 0.5257 0.6441 0.168 Uiso 0.308(10) 1 calc R U P A 2
H4B2_b H 0.8602 0.4423 0.6048 0.168 Uiso 0.308(10) 1 calc R U P A 2
H4B3_b H 0.7901 0.4211 0.6654 0.168 Uiso 0.308(10) 1 calc R U P A 2
H3A_a H 0.694(7) 0.457(10) 0.630(5) 0.134 Uiso 0.692(10) 1 d D U P A 1
H3B_b H 0.49(4) 0.385(4) 0.623(9) 0.134 Uiso 0.308(10) 1 d D 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 C11 1.418(3) . ?
O1 H1O 0.85(4) . ?
N1 C10 1.466(3) . ?
N1 C1 1.468(3) . ?
N1 H1N 0.96(3) . ?
N2 C7 1.346(3) . ?
N2 N3 1.346(3) . ?
N2 C2 1.455(3) . ?
N3 N4 1.313(3) . ?
N4 C6 1.358(3) . ?
C7 C6 1.363(3) . ?
C7 H7 0.9300 . ?
C6 C61 1.468(3) . ?
C61 C62 1.378(4) . ?
C61 C66 1.379(4) . ?
C1 C3 1.530(4) . ?
C1 C2 1.539(3) . ?
C1 H1 0.9800 . ?
C12 C13 1.370(4) . ?
C12 C17 1.391(4) . ?
C12 C11 1.519(3) . ?
C11 C10 1.523(3) . ?
C11 H11 0.9800 . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
C10 H15A 0.9700 . ?
C10 H10A 0.9700 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9300 . ?
C17 C16 1.381(5) . ?
C17 H17 0.9300 . ?
C62 C63 1.383(5) . ?
C62 H52 0.9300 . ?
C66 C65 1.386(5) . ?
C66 H66 0.9300 . ?
C64 C65 1.356(5) . ?
C64 C63 1.371(5) . ?
C64 H64 0.9300 . ?
C65 H65 0.9300 . ?
C63 H63 0.9300 . ?
C15 C16 1.359(6) . ?
C15 C14 1.360(6) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C5 C3 1.546(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5D 0.9600 . ?
C3 C4B_b 1.365(11) . ?
C3 C4A_a 1.448(5) . ?
C3 H3A_a 0.977(14) . ?
C3 H3B_b 0.979(14) . ?
C4A_a H4A1_a 0.9600 . ?
C4A_a H4A2_a 0.9600 . ?
C4A_a H4A3_a 0.9600 . ?
C4B_b H4B1_b 0.9600 . ?
C4B_b H4B2_b 0.9600 . ?
C4B_b H4B3_b 0.9600 . ?

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
C11 O1 H1O 106(3) . . ?
C10 N1 C1 116.86(18) . . ?
C10 N1 H1N 109.1(15) . . ?
C1 N1 H1N 109.5(15) . . ?
C7 N2 N3 110.8(2) . . ?
C7 N2 C2 128.83(18) . . ?
N3 N2 C2 120.4(2) . . ?
N4 N3 N2 106.7(2) . . ?
N3 N4 C6 109.38(19) . . ?
N2 C7 C6 105.11(18) . . ?
N2 C7 H7 127.4 . . ?
C6 C7 H7 127.4 . . ?
N4 C6 C7 108.03(19) . . ?
N4 C6 C61 122.1(2) . . ?
C7 C6 C61 129.9(2) . . ?
C62 C61 C66 118.1(2) . . ?
C62 C61 C6 121.0(2) . . ?
C66 C61 C6 120.9(2) . . ?
N1 C1 C3 113.3(2) . . ?
N1 C1 C2 113.39(18) . . ?
C3 C1 C2 109.9(2) . . ?
N1 C1 H1 106.6 . . ?
C3 C1 H1 106.6 . . ?
C2 C1 H1 106.6 . . ?
C13 C12 C17 118.1(3) . . ?
C13 C12 C11 121.4(2) . . ?
C17 C12 C11 120.4(2) . . ?
O1 C11 C12 110.5(2) . . ?
O1 C11 C10 110.01(19) . . ?
C12 C11 C10 111.13(18) . . ?
O1 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C10 C11 H11 108.4 . . ?
N2 C2 C1 111.07(18) . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
H2B C2 H2A 108.0 . . ?
N1 C10 C11 110.81(18) . . ?
N1 C10 H15A 109.5 . . ?
C11 C10 H15A 109.5 . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
H15A C10 H10A 108.1 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C16 C17 C12 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C61 C62 C63 120.8(3) . . ?
C61 C62 H52 119.6 . . ?
C63 C62 H52 119.6 . . ?
C61 C66 C65 120.5(3) . . ?
C61 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
C65 C64 C63 118.9(3) . . ?
C65 C64 H64 120.6 . . ?
C63 C64 H64 120.6 . . ?
C64 C65 C66 121.1(3) . . ?
C64 C65 H65 119.4 . . ?
C66 C65 H65 119.4 . . ?
C64 C63 C62 120.6(3) . . ?
C64 C63 H63 119.7 . . ?
C62 C63 H63 119.7 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5D 109.5 . . ?
H5A C5 H5D 109.5 . . ?
H5B C5 H5D 109.5 . . ?
C4B_b C3 C1 126.9(11) . . ?
C4A_a C3 C1 113.5(3) . . ?
C4B_b C3 C5 92.3(11) . . ?
C4A_a C3 C5 110.0(4) . . ?
C1 C3 C5 111.7(3) . . ?
C4A_a C3 H3A_a 99(9) . . ?
C1 C3 H3A_a 127(8) . . ?
C5 C3 H3A_a 93(8) . . ?
C4B_b C3 H3B_b 105(10) . . ?
C1 C3 H3B_b 106(10) . . ?
C5 C3 H3B_b 115(10) . . ?
C3 C4A_a H4A1_a 109.5 . . ?
C3 C4A_a H4A2_a 109.5 . . ?
H4A1_a C4A_a H4A2_a 109.5 . . ?
C3 C4A_a H4A3_a 109.5 . . ?
H4A1_a C4A_a H4A3_a 109.5 . . ?
H4A2_a C4A_a H4A3_a 109.5 . . ?
C3 C4B_b H4B1_b 109.5 . . ?
C3 C4B_b H4B2_b 109.5 . . ?
H4B1_b C4B_b H4B2_b 109.5 . . ?
C3 C4B_b H4B3_b 109.5 . . ?
H4B1_b C4B_b H4B3_b 109.5 . . ?
H4B2_b C4B_b H4B3_b 109.5 . . ?

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2501473'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 N4 O'
_chemical_formula_weight         262.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.99300(10)
_cell_length_b                   15.3371(4)
_cell_length_c                   16.5036(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1516.93(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294.8(2)
_cell_measurement_reflns_used    7532
_cell_measurement_theta_min      3.9050
_cell_measurement_theta_max      71.3490

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.598
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.66885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.424
_oxdiff_exptl_absorpt_empirical_full_max 1.561
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      294.8(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14368
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.935
_diffrn_reflns_theta_max         76.287
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3072
_reflns_number_gt                2666
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0482P)²+0.1128P] 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
_refine_ls_extinction_coef       0.0023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1011 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(14)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3072
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C11 C 0.8678(3) 0.72139(14) 0.40383(12) 0.0506(5) Uani 1 1 d . . . . .
H11 H 0.9225 0.7722 0.4338 0.061 Uiso 1 1 calc R U . . .
N1 N 0.9631(3) 0.63078(12) 0.52035(10) 0.0515(4) Uani 1 1 d . . . . .
O1 O 0.6389(2) 0.70918(12) 0.42259(9) 0.0591(4) Uani 1 1 d . . . . .
C12 C 0.9077(3) 0.73658(13) 0.31434(12) 0.0492(4) Uani 1 1 d . . . . .
C1 C 1.0659(3) 0.55297(14) 0.55680(13) 0.0542(5) Uani 1 1 d . . . . .
H10 H 1.2278 0.5575 0.5495 0.065 Uiso 1 1 calc R U . . .
C4 C 1.1194(4) 0.48603(16) 0.70160(15) 0.0641(6) Uani 1 1 d . . . . .
H4 H 1.0664 0.4291 0.6826 0.077 Uiso 1 1 calc R U . . .
C13 C 0.7440(4) 0.72043(15) 0.25718(13) 0.0583(5) Uani 1 1 d . . . . .
H13 H 0.6053 0.6996 0.2734 0.070 Uiso 1 1 calc R U . . .
C10 C 0.9938(4) 0.64131(15) 0.43282(12) 0.0552(5) Uani 1 1 d . . . . .
H10B H 0.9390 0.5900 0.4048 0.066 Uiso 1 1 calc R U . . .
H10A H 1.1513 0.6476 0.4206 0.066 Uiso 1 1 calc R U . . .
C3 C 1.0176(4) 0.55640(16) 0.64777(14) 0.0572(5) Uani 1 1 d . . . . .
H4B H 1.0680 0.6125 0.6678 0.069 Uiso 1 1 calc R U . . .
H3A H 0.8570 0.5545 0.6549 0.069 Uiso 1 1 calc R U . . .
C14 C 0.7862(4) 0.73526(19) 0.17574(15) 0.0703(7) Uani 1 1 d . . . . .
H14 H 0.6753 0.7244 0.1376 0.084 Uiso 1 1 calc R U . . .
C2 C 0.9897(4) 0.46805(17) 0.51780(17) 0.0693(6) Uani 1 1 d . . . . .
H2A H 1.0353 0.4662 0.4614 0.083 Uiso 1 1 calc R U . . .
H2B H 1.0554 0.4186 0.5457 0.083 Uiso 1 1 calc R U . . .
C16 C 1.1538(4) 0.7810(2) 0.20684(16) 0.0773(7) Uani 1 1 d . . . . .
H16 H 1.2928 0.8011 0.1901 0.093 Uiso 1 1 calc R U . . .
N3 N 0.6488(5) 0.40445(19) 0.49406(14) 0.0854(7) Uani 1 1 d . . . . .
C15 C 0.9899(5) 0.7658(2) 0.15093(15) 0.0758(7) Uani 1 1 d . . . . .
H15 H 1.0167 0.7761 0.0963 0.091 Uiso 1 1 calc R U . . .
C17 C 1.1130(4) 0.76646(17) 0.28794(15) 0.0657(6) Uani 1 1 d . . . . .
H17 H 1.2254 0.7769 0.3255 0.079 Uiso 1 1 calc R U . . .
C42 C 1.0408(5) 0.4987(2) 0.78840(18) 0.0852(8) Uani 1 1 d . . . . .
HH2B H 1.0949 0.5534 0.8086 0.128 Uiso 1 1 calc R U . . .
H42C H 1.0972 0.4522 0.8216 0.128 Uiso 1 1 calc R U . . .
H42A H 0.8806 0.4983 0.7899 0.128 Uiso 1 1 calc R U . . .
C41 C 1.3715(5) 0.4860(2) 0.6988(2) 0.0981(10) Uani 1 1 d . . . . .
H41A H 1.4204 0.4736 0.6446 0.147 Uiso 1 1 calc R U . . .
H41B H 1.4278 0.4421 0.7350 0.147 Uiso 1 1 calc R U . . .
H41C H 1.4263 0.5421 0.7151 0.147 Uiso 1 1 calc R U . . .
N2 N 0.7427(4) 0.46482(19) 0.52402(19) 0.0997(9) Uani 1 1 d . . . . .
N4 N 0.5403(6) 0.3505(3) 0.46960(19) 0.1291(13) Uani 1 1 d . . . . .
H1O H 0.582(6) 0.759(2) 0.438(2) 0.094(10) Uiso 1 1 d . . . . .
H1 H 0.821(4) 0.6284(15) 0.5293(13) 0.051(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 O1 1.419(2) . ?
C11 C12 1.514(3) . ?
C11 C10 1.519(3) . ?
N1 C10 1.465(3) . ?
N1 C1 1.472(3) . ?
C12 C13 1.383(3) . ?
C12 C17 1.384(3) . ?
C1 C2 1.523(4) . ?
C1 C3 1.530(3) . ?
C4 C41 1.511(4) . ?
C4 C42 1.520(4) . ?
C4 C3 1.525(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.370(4) . ?
C2 N2 1.485(4) . ?
C16 C15 1.368(4) . ?
C16 C17 1.379(4) . ?
N3 N4 1.127(4) . ?
N3 N2 1.191(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 C11 C12 112.68(16) . . ?
O1 C11 C10 107.77(18) . . ?
C12 C11 C10 110.68(17) . . ?
C10 N1 C1 116.09(17) . . ?
C13 C12 C17 118.38(19) . . ?
C13 C12 C11 121.73(18) . . ?
C17 C12 C11 119.89(18) . . ?
N1 C1 C2 113.27(18) . . ?
N1 C1 C3 107.09(17) . . ?
C2 C1 C3 112.79(19) . . ?
C41 C4 C42 109.8(3) . . ?
C41 C4 C3 112.5(2) . . ?
C42 C4 C3 109.5(2) . . ?
C12 C13 C14 120.2(2) . . ?
N1 C10 C11 109.70(17) . . ?
C4 C3 C1 118.12(19) . . ?
C15 C14 C13 120.5(2) . . ?
N2 C2 C1 107.4(2) . . ?
C15 C16 C17 120.0(2) . . ?
N4 N3 N2 172.7(4) . . ?
C16 C15 C14 119.8(2) . . ?
C16 C17 C12 121.1(2) . . ?
N3 N2 C2 117.9(3) . . ?

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.026

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2501471'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 N4 O'
_chemical_formula_weight         248.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.76270(10)
_cell_length_b                   12.3209(2)
_cell_length_c                   17.7941(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1482.65(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294.23(10)
_cell_measurement_reflns_used    10444
_cell_measurement_theta_min      4.3320
_cell_measurement_theta_max      76.5370

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.588
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.72257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.461
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      294.23(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14244
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.365
_diffrn_reflns_theta_max         76.737
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2967
_reflns_number_gt                2776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_max     0.911
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0505P)²+0.1070P] 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
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2967
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 -0.0593(2) 0.72369(12) 0.45932(8) 0.0647(4) Uani 1 1 d . . . . .
N1 N 0.2471(2) 0.58672(10) 0.49304(8) 0.0468(3) Uani 1 1 d . . . . .
C2 C 0.2921(2) 0.47134(12) 0.50594(9) 0.0475(4) Uani 1 1 d . . . . .
H2 H 0.1801 0.4284 0.4875 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1990(3) 0.61448(13) 0.41499(9) 0.0503(4) Uani 1 1 d . . . . .
H10B H 0.1062 0.5620 0.3948 0.060 Uiso 1 1 calc R U . . .
H10A H 0.3179 0.6125 0.3846 0.060 Uiso 1 1 calc R U . . .
C12 C 0.0582(3) 0.76032(14) 0.33268(10) 0.0564(4) Uani 1 1 d . . . . .
C11 C 0.1089(3) 0.72717(14) 0.41222(9) 0.0495(4) Uani 1 1 d . . . . .
H11 H 0.2039 0.7793 0.4330 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4781(3) 0.43468(15) 0.46330(11) 0.0571(4) Uani 1 1 d . . . . .
H4 H 0.4578 0.4545 0.4105 0.068 Uiso 1 1 calc R U . . .
N31 N 0.1088(3) 0.4752(2) 0.62237(9) 0.0847(6) Uani 1 1 d . . . . .
N32 N 0.0925(3) 0.46819(19) 0.68918(10) 0.0850(6) Uani 1 1 d . . . . .
C3 C 0.3066(3) 0.45498(17) 0.59018(11) 0.0590(5) Uani 1 1 d . . . . .
H3B H 0.3489 0.3815 0.6013 0.071 Uiso 1 1 calc R U . . .
H3A H 0.4022 0.5050 0.6115 0.071 Uiso 1 1 calc R U . . .
C42 C 0.5020(3) 0.31221(17) 0.46530(15) 0.0762(6) Uani 1 1 d . . . . .
H42B H 0.5390 0.2900 0.5150 0.114 Uiso 1 1 calc R U . . .
H42A H 0.6029 0.2908 0.4304 0.114 Uiso 1 1 calc R U . . .
H42C H 0.3791 0.2784 0.4518 0.114 Uiso 1 1 calc R U . . .
C17 C 0.1871(5) 0.8221(2) 0.29208(13) 0.0869(7) Uani 1 1 d . . . . .
H16 H 0.3060 0.8433 0.3138 0.104 Uiso 1 1 calc R U . . .
C16 C 0.1445(7) 0.8539(3) 0.21891(15) 0.1134(11) Uani 1 1 d . . . . .
H15 H 0.2337 0.8965 0.1922 0.136 Uiso 1 1 calc R U . . .
C41 C 0.6646(4) 0.4912(2) 0.48833(19) 0.1014(10) Uani 1 1 d . . . . .
H41A H 0.6515 0.5679 0.4802 0.152 Uiso 1 1 calc R U . . .
H41C H 0.7748 0.4642 0.4599 0.152 Uiso 1 1 calc R U . . .
H41B H 0.6863 0.4775 0.5408 0.152 Uiso 1 1 calc R U . . .
C13 C -0.1144(5) 0.7304(3) 0.29892(15) 0.0966(8) Uani 1 1 d . . . . .
H12 H -0.2053 0.6887 0.3254 0.116 Uiso 1 1 calc R U . . .
C15 C -0.0278(7) 0.8225(3) 0.18664(16) 0.1149(13) Uani 1 1 d . . . . .
H14 H -0.0569 0.8432 0.1376 0.138 Uiso 1 1 calc R U . . .
N33 N 0.0584(5) 0.4636(3) 0.75047(14) 0.1504(15) Uani 1 1 d . . . . .
C14 C -0.1566(6) 0.7613(3) 0.22585(18) 0.1229(12) Uani 1 1 d . . . . .
H13 H -0.2747 0.7396 0.2037 0.147 Uiso 1 1 calc R U . . .
H1N H 0.139(3) 0.6020(16) 0.5191(11) 0.054(5) Uiso 1 1 d . . . . .
H1O H -0.099(4) 0.787(2) 0.4704(13) 0.082(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.413(2) . ?
O1 H1O 0.84(3) . ?
N1 C10 1.467(2) . ?
N1 C2 1.472(2) . ?
N1 H1N 0.88(2) . ?
C2 C3 1.516(2) . ?
C2 C4 1.537(2) . ?
C2 H2 0.9800 . ?
C10 C11 1.517(2) . ?
C10 H10B 0.9700 . ?
C10 H10A 0.9700 . ?
C12 C17 1.364(3) . ?
C12 C13 1.364(3) . ?
C12 C11 1.513(2) . ?
C11 H11 0.9800 . ?
C4 C41 1.508(3) . ?
C4 C42 1.518(3) . ?
C4 H4 0.9800 . ?
N31 N32 1.197(2) . ?
N31 C3 1.477(3) . ?
N32 N33 1.116(3) . ?
C3 H3B 0.9700 . ?
C3 H3A 0.9700 . ?
C42 H42B 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42C 0.9600 . ?
C17 C16 1.390(3) . ?
C17 H16 0.9300 . ?
C16 C15 1.355(5) . ?
C16 H15 0.9300 . ?
C41 H41A 0.9600 . ?
C41 H41C 0.9600 . ?
C41 H41B 0.9600 . ?
C13 C14 1.384(4) . ?
C13 H12 0.9300 . ?
C15 C14 1.347(5) . ?
C15 H14 0.9300 . ?
C14 H13 0.9300 . ?

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
C11 O1 H1O 111.6(18) . . ?
C10 N1 C2 114.76(13) . . ?
C10 N1 H1N 105.3(12) . . ?
C2 N1 H1N 107.1(13) . . ?
N1 C2 C3 107.22(14) . . ?
N1 C2 C4 112.08(14) . . ?
C3 C2 C4 113.33(15) . . ?
N1 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C4 C2 H2 108.0 . . ?
N1 C10 C11 109.47(13) . . ?
N1 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
N1 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
H10B C10 H10A 108.2 . . ?
C17 C12 C13 117.7(2) . . ?
C17 C12 C11 120.11(19) . . ?
C13 C12 C11 122.2(2) . . ?
O1 C11 C12 112.39(15) . . ?
O1 C11 C10 106.04(14) . . ?
C12 C11 C10 111.62(14) . . ?
O1 C11 H11 108.9 . . ?
C12 C11 H11 108.9 . . ?
C10 C11 H11 108.9 . . ?
C41 C4 C42 111.32(19) . . ?
C41 C4 C2 113.76(16) . . ?
C42 C4 C2 111.56(16) . . ?
C41 C4 H4 106.6 . . ?
C42 C4 H4 106.6 . . ?
C2 C4 H4 106.6 . . ?
N32 N31 C3 117.16(19) . . ?
N33 N32 N31 173.2(3) . . ?
N31 C3 C2 107.61(15) . . ?
N31 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
N31 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
H3B C3 H3A 108.5 . . ?
C4 C42 H42B 109.5 . . ?
C4 C42 H42A 109.5 . . ?
H42B C42 H42A 109.5 . . ?
C4 C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
C12 C17 C16 121.4(3) . . ?
C12 C17 H16 119.3 . . ?
C16 C17 H16 119.3 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H15 120.2 . . ?
C17 C16 H15 120.2 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41C C41 H41B 109.5 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H12 119.5 . . ?
C14 C13 H12 119.5 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H14 120.1 . . ?
C16 C15 H14 120.1 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H13 119.8 . . ?
C13 C14 H13 119.8 . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.023

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2501470'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 N O'
_chemical_formula_weight         205.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   8.49900(10)
_cell_length_b                   10.50350(10)
_cell_length_c                   13.59500(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1213.62(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(4)
_cell_measurement_reflns_used    9510
_cell_measurement_theta_min      3.2060
_cell_measurement_theta_max      76.2870

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.547
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.687
_oxdiff_exptl_absorpt_empirical_full_max 1.292
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.0(4)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            11530
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.322
_diffrn_reflns_theta_max         76.463
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2423
_reflns_number_gt                2372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_max     0.920
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0355P)²+0.1868P] 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
_refine_ls_extinction_coef       0.0058(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 956 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2423
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1 N 0.55342(13) 0.62500(11) 0.43238(9) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.72983(16) 0.80964(13) 0.41099(10) 0.0198(3) Uani 1 1 d . . . . .
H11 H 0.6799 0.8442 0.4720 0.024 Uiso 1 1 calc R U . . .
C3 C 0.49740(17) 0.50398(13) 0.38886(11) 0.0253(3) Uani 1 1 d . . . . .
H3B H 0.5046 0.4941 0.3166 0.030 Uiso 1 1 calc R U . . .
H3A H 0.4054 0.4621 0.4197 0.030 Uiso 1 1 calc R U . . .
C2 C 0.64635(16) 0.50817(13) 0.44565(10) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.7448 0.5029 0.4056 0.024 Uiso 1 1 calc R U . . .
C10 C 0.61567(16) 0.71767(13) 0.36175(10) 0.0200(3) Uani 1 1 d . . . . .
H10A H 0.5275 0.7662 0.3325 0.024 Uiso 1 1 calc R U . . .
H10B H 0.6704 0.6721 0.3080 0.024 Uiso 1 1 calc R U . . .
C17 C 0.86791(18) 0.89877(15) 0.26204(10) 0.0251(3) Uani 1 1 d . . . . .
H17 H 0.9071 0.8157 0.2492 0.030 Uiso 1 1 calc R U . . .
C12 C 0.77088(17) 0.91960(13) 0.34320(10) 0.0202(3) Uani 1 1 d . . . . .
C16 C 0.90767(18) 0.99868(17) 0.19991(11) 0.0315(4) Uani 1 1 d . . . . .
H16 H 0.9736 0.9836 0.1447 0.038 Uiso 1 1 calc R U . . .
C13 C 0.71613(18) 1.04199(14) 0.36106(11) 0.0242(3) Uani 1 1 d . . . . .
H13 H 0.6509 1.0577 0.4165 0.029 Uiso 1 1 calc R U . . .
C4 C 0.65783(18) 0.45395(13) 0.54815(10) 0.0235(3) Uani 1 1 d . . . . .
H4 H 0.5507 0.4563 0.5785 0.028 Uiso 1 1 calc R U . . .
C14 C 0.7559(2) 1.14216(15) 0.29848(12) 0.0319(4) Uani 1 1 d . . . . .
H14 H 0.7171 1.2254 0.3111 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8517(2) 1.12023(16) 0.21808(12) 0.0338(4) Uani 1 1 d . . . . .
H15 H 0.8791 1.1884 0.1754 0.041 Uiso 1 1 calc R U . . .
C41 C 0.7681(2) 0.53292(16) 0.61171(11) 0.0322(4) Uani 1 1 d . . . . .
H41B H 0.8753 0.5274 0.5855 0.048 Uiso 1 1 calc R U . . .
H41C H 0.7665 0.5003 0.6793 0.048 Uiso 1 1 calc R U . . .
H41A H 0.7336 0.6219 0.6114 0.048 Uiso 1 1 calc R U . . .
C42 C 0.7108(3) 0.31557(15) 0.54236(14) 0.0402(4) Uani 1 1 d . . . . .
HH2C H 0.6334 0.2662 0.5049 0.060 Uiso 1 1 calc R U . . .
H42B H 0.7197 0.2805 0.6089 0.060 Uiso 1 1 calc R U . . .
H42A H 0.8132 0.3109 0.5095 0.060 Uiso 1 1 calc R U . . .
O1 O 0.86587(12) 0.73871(9) 0.43751(8) 0.0234(2) Uani 1 1 d . . . . .
H1 H 0.928(3) 0.792(2) 0.4770(16) 0.051(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C10 1.4661(18) . ?
N1 C2 1.4705(17) . ?
N1 C3 1.4807(17) . ?
C11 O1 1.4220(17) . ?
C11 C12 1.5182(19) . ?
C11 C10 1.5240(19) . ?
C3 C2 1.483(2) . ?
C2 C4 1.5085(19) . ?
C17 C16 1.389(2) . ?
C17 C12 1.395(2) . ?
C12 C13 1.389(2) . ?
C16 C15 1.385(3) . ?
C13 C14 1.395(2) . ?
C4 C41 1.521(2) . ?
C4 C42 1.524(2) . ?
C14 C15 1.383(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
C10 N1 C2 116.14(11) . . ?
C10 N1 C3 115.11(11) . . ?
C2 N1 C3 60.35(9) . . ?
O1 C11 C12 111.45(11) . . ?
O1 C11 C10 107.27(11) . . ?
C12 C11 C10 111.21(11) . . ?
N1 C3 C2 59.49(9) . . ?
N1 C2 C3 60.16(9) . . ?
N1 C2 C4 117.59(11) . . ?
C3 C2 C4 121.65(12) . . ?
N1 C10 C11 111.28(11) . . ?
C16 C17 C12 120.43(15) . . ?
C13 C12 C17 118.80(13) . . ?
C13 C12 C11 121.40(13) . . ?
C17 C12 C11 119.79(13) . . ?
C15 C16 C17 120.31(15) . . ?
C12 C13 C14 120.70(15) . . ?
C2 C4 C41 111.03(12) . . ?
C2 C4 C42 109.37(12) . . ?
C41 C4 C42 111.57(14) . . ?
C15 C14 C13 119.96(15) . . ?
C14 C15 C16 119.81(14) . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2501472'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 N4 O'
_chemical_formula_weight         350.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.60710(10)
_cell_length_b                   14.1175(3)
_cell_length_c                   24.5345(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1942.11(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294.56(10)
_cell_measurement_reflns_used    13400
_cell_measurement_theta_min      3.1450
_cell_measurement_theta_max      75.7460

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.597
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.35477
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.462
_oxdiff_exptl_absorpt_empirical_full_max 1.781
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      294.56(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            18165
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.612
_diffrn_reflns_theta_max         76.035
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3823
_reflns_number_gt                3501
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_max     0.910
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1427P)²+0.0729P] 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
_refine_ls_extinction_coef       0.0055(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1349 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3823
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.6707(4) 0.25260(14) 0.52870(11) 0.0700(6) Uani 1 1 d D . . . .
N1 N 0.4715(4) 0.42012(16) 0.47990(10) 0.0519(5) Uani 1 1 d . . . . .
N2 N 0.3596(4) 0.62204(15) 0.49482(10) 0.0513(5) Uani 1 1 d . . . . .
N3 N 0.1194(4) 0.6212(2) 0.49806(12) 0.0630(7) Uani 1 1 d . . . . .
N4 N 0.0642(4) 0.65386(19) 0.54652(12) 0.0636(7) Uani 1 1 d . . . . .
C7 C 0.4561(5) 0.65592(19) 0.54130(12) 0.0528(6) Uani 1 1 d . . . . .
H7 H 0.6169 0.6641 0.5493 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2660(5) 0.67549(17) 0.57396(12) 0.0512(6) Uani 1 1 d . . . . .
C12 C 0.6174(5) 0.3800(2) 0.59327(11) 0.0568(7) Uani 1 1 d . . . . .
C61 C 0.2620(5) 0.71332(19) 0.62987(12) 0.0559(6) Uani 1 1 d . . . . .
C1 C 0.4149(5) 0.4847(2) 0.43444(11) 0.0556(6) Uani 1 1 d . . . . .
H1 H 0.2415 0.4825 0.4296 0.067 Uiso 1 1 calc R U . . .
C11 C 0.7512(5) 0.3436(2) 0.54342(12) 0.0582(6) Uani 1 1 d . . . . .
H11 H 0.9211 0.3395 0.5525 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7224(5) 0.4120(2) 0.49542(11) 0.0581(6) Uani 1 1 d . . . . .
H15A H 0.7832 0.4739 0.5055 0.070 Uiso 1 1 calc R U . . .
H15B H 0.8144 0.3893 0.4646 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4787(5) 0.5879(2) 0.44598(12) 0.0583(7) Uani 1 1 d . . . . .
H5A H 0.6499 0.5936 0.4505 0.070 Uiso 1 1 calc R U . . .
H5B H 0.4322 0.6267 0.4151 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4129(7) 0.3373(3) 0.61093(15) 0.0740(9) Uani 1 1 d . . . . .
H13 H 0.3574 0.2831 0.5934 0.089 Uiso 1 1 calc R U . . .
C17 C 0.6969(8) 0.4595(2) 0.62052(14) 0.0772(10) Uani 1 1 d . . . . .
H17 H 0.8362 0.4894 0.6092 0.093 Uiso 1 1 calc R U . . .
C62 C 0.0730(7) 0.6937(3) 0.66393(16) 0.0759(9) Uani 1 1 d . . . . .
H62 H -0.0554 0.6587 0.6510 0.091 Uiso 1 1 calc R U . . .
C66 C 0.4481(7) 0.7660(3) 0.64983(16) 0.0800(10) Uani 1 1 d . . . . .
H66 H 0.5755 0.7816 0.6273 0.096 Uiso 1 1 calc R U . . .
C64 C 0.2615(8) 0.7774(3) 0.73738(16) 0.0845(10) Uani 1 1 d . . . . .
H64 H 0.2620 0.7989 0.7732 0.101 Uiso 1 1 calc R U . . .
C65 C 0.4463(8) 0.7963(4) 0.70378(18) 0.0921(13) Uani 1 1 d . . . . .
H65 H 0.5758 0.8304 0.7171 0.111 Uiso 1 1 calc R U . . .
C15 C 0.3676(10) 0.4531(3) 0.68150(15) 0.0905(13) Uani 1 1 d . . . . .
H15 H 0.2830 0.4776 0.7109 0.109 Uiso 1 1 calc R U . . .
C63 C 0.0727(9) 0.7259(4) 0.71743(17) 0.0894(12) Uani 1 1 d . . . . .
H63 H -0.0563 0.7125 0.7399 0.107 Uiso 1 1 calc R U . . .
C2 C 0.5254(9) 0.4524(3) 0.37996(13) 0.0827(11) Uani 1 1 d . . . . .
H2 H 0.6745 0.4660 0.3774 0.099 Uiso 1 1 d R U . . .
C14 C 0.2877(8) 0.3741(4) 0.65485(17) 0.0924(12) Uani 1 1 d . . . . .
H14 H 0.1479 0.3448 0.6663 0.111 Uiso 1 1 calc R U . . .
C16 C 0.5710(10) 0.4952(3) 0.66454(16) 0.0889(13) Uani 1 1 d . . . . .
H22 H 0.6271 0.5486 0.6826 0.107 Uiso 1 1 calc R U . . .
C3 C 0.4829(16) 0.3539(4) 0.3679(2) 0.128(3) Uani 1 1 d . . . . .
H32 H 0.6001 0.3319 0.3423 0.192 Uiso 1 1 calc R U . . .
H33 H 0.3266 0.3468 0.3524 0.192 Uiso 1 1 calc R U . . .
H31 H 0.4937 0.3175 0.4008 0.192 Uiso 1 1 calc R U . . .
C4 C 0.4432(19) 0.5169(5) 0.33216(19) 0.155(4) Uani 1 1 d . . . . .
H42 H 0.2756 0.5080 0.3259 0.233 Uiso 1 1 calc R U . . .
H43 H 0.5300 0.5006 0.2998 0.233 Uiso 1 1 calc R U . . .
H41 H 0.4730 0.5820 0.3412 0.233 Uiso 1 1 calc R U . . .
H1N H 0.389(5) 0.440(2) 0.5100(12) 0.041(7) Uiso 1 1 d . . . . .
H1O H 0.804(6) 0.222(4) 0.523(2) 0.109(16) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.409(4) . ?
O1 H1O 0.87(3) . ?
N1 C10 1.462(4) . ?
N1 C1 1.475(3) . ?
N1 H1N 0.91(3) . ?
N2 N3 1.349(3) . ?
N2 C7 1.350(4) . ?
N2 C5 1.454(4) . ?
N3 N4 1.312(4) . ?
N4 C6 1.351(4) . ?
C7 C6 1.362(4) . ?
C7 H7 0.9300 . ?
C6 C61 1.472(4) . ?
C12 C13 1.366(5) . ?
C12 C17 1.380(5) . ?
C12 C11 1.524(4) . ?
C61 C66 1.372(5) . ?
C61 C62 1.377(5) . ?
C1 C5 1.526(4) . ?
C1 C2 1.542(4) . ?
C1 H1 0.9800 . ?
C11 C10 1.532(4) . ?
C11 H11 0.9800 . ?
C10 H15A 0.9700 . ?
C10 H15B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C13 C14 1.387(6) . ?
C13 H13 0.9300 . ?
C17 C16 1.385(6) . ?
C17 H17 0.9300 . ?
C62 C63 1.389(6) . ?
C62 H62 0.9300 . ?
C66 C65 1.391(6) . ?
C66 H66 0.9300 . ?
C64 C65 1.350(6) . ?
C64 C63 1.374(6) . ?
C64 H64 0.9300 . ?
C65 H65 0.9300 . ?
C15 C16 1.352(7) . ?
C15 C14 1.368(8) . ?
C15 H15 0.9300 . ?
C63 H63 0.9300 . ?
C2 C3 1.442(7) . ?
C2 C4 1.555(7) . ?
C2 H2 0.8600 . ?
C14 H14 0.9300 . ?
C16 H22 0.9300 . ?
C3 H32 0.9600 . ?
C3 H33 0.9600 . ?
C3 H31 0.9600 . ?
C4 H42 0.9600 . ?
C4 H43 0.9600 . ?
C4 H41 0.9600 . ?

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
C11 O1 H1O 103(4) . . ?
C10 N1 C1 116.9(2) . . ?
C10 N1 H1N 107.4(18) . . ?
C1 N1 H1N 108.5(18) . . ?
N3 N2 C7 110.7(3) . . ?
N3 N2 C5 120.3(3) . . ?
C7 N2 C5 129.0(2) . . ?
N4 N3 N2 106.6(3) . . ?
N3 N4 C6 109.5(2) . . ?
N2 C7 C6 104.8(2) . . ?
N2 C7 H7 127.6 . . ?
C6 C7 H7 127.6 . . ?
N4 C6 C7 108.4(2) . . ?
N4 C6 C61 122.2(3) . . ?
C7 C6 C61 129.3(2) . . ?
C13 C12 C17 118.5(3) . . ?
C13 C12 C11 121.2(3) . . ?
C17 C12 C11 120.3(3) . . ?
C66 C61 C62 118.5(3) . . ?
C66 C61 C6 121.2(3) . . ?
C62 C61 C6 120.3(3) . . ?
N1 C1 C5 113.5(2) . . ?
N1 C1 C2 112.7(3) . . ?
C5 C1 C2 110.4(3) . . ?
N1 C1 H1 106.5 . . ?
C5 C1 H1 106.5 . . ?
C2 C1 H1 106.5 . . ?
O1 C11 C12 110.8(3) . . ?
O1 C11 C10 110.1(2) . . ?
C12 C11 C10 110.6(2) . . ?
O1 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C10 C11 H11 108.4 . . ?
N1 C10 C11 110.6(2) . . ?
N1 C10 H15A 109.5 . . ?
C11 C10 H15A 109.5 . . ?
N1 C10 H15B 109.5 . . ?
C11 C10 H15B 109.5 . . ?
H15A C10 H15B 108.1 . . ?
N2 C5 C1 111.2(2) . . ?
N2 C5 H5A 109.4 . . ?
C1 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
C1 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C12 C17 C16 120.6(4) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C61 C62 C63 120.6(4) . . ?
C61 C62 H62 119.7 . . ?
C63 C62 H62 119.7 . . ?
C61 C66 C65 120.0(4) . . ?
C61 C66 H66 120.0 . . ?
C65 C66 H66 120.0 . . ?
C65 C64 C63 118.5(4) . . ?
C65 C64 H64 120.7 . . ?
C63 C64 H64 120.7 . . ?
C64 C65 C66 121.7(4) . . ?
C64 C65 H65 119.1 . . ?
C66 C65 H65 119.1 . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C64 C63 C62 120.6(4) . . ?
C64 C63 H63 119.7 . . ?
C62 C63 H63 119.7 . . ?
C3 C2 C1 113.4(4) . . ?
C3 C2 C4 111.1(4) . . ?
C1 C2 C4 111.2(4) . . ?
C3 C2 H2 111.1 . . ?
C1 C2 H2 112.9 . . ?
C4 C2 H2 95.9 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H22 119.6 . . ?
C17 C16 H22 119.6 . . ?
C2 C3 H32 109.5 . . ?
C2 C3 H33 109.5 . . ?
H32 C3 H33 109.5 . . ?
C2 C3 H31 109.5 . . ?
H32 C3 H31 109.5 . . ?
H33 C3 H31 109.5 . . ?
C2 C4 H42 109.5 . . ?
C2 C4 H43 109.5 . . ?
H42 C4 H43 109.5 . . ?
C2 C4 H41 109.5 . . ?
H42 C4 H41 109.5 . . ?
H43 C4 H41 109.5 . . ?

_refine_diff_density_max         0.747
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2501479'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N4 O'
_chemical_formula_weight         384.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.7923(2)
_cell_length_b                   5.69560(10)
_cell_length_c                   15.1879(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.498(2)
_cell_angle_gamma                90
_cell_volume                     1043.13(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293.79(10)
_cell_measurement_reflns_used    14643
_cell_measurement_theta_min      3.0520
_cell_measurement_theta_max      75.8930

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.608
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.41930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.333
_oxdiff_exptl_absorpt_empirical_full_max 1.545
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      293.79(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            19462
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         68.977
_diffrn_reflns_theta_full        67.684
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3849
_reflns_number_gt                3671
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1183P)²+0.1135P] 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
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3849
_refine_ls_number_parameters     278
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1691
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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
C11 C 0.3590(7) 0.8399(13) 0.4522(4) 0.157(3) Uani 1 1 d D U . . .
H11A_a H 0.3071 0.9344 0.4001 0.188 Uiso 1 1 d . U . A 1
H11B_a H 0.3698 0.6998 0.4163 0.188 Uiso 1 1 d . U . B 1
H11C_b H 0.3243 0.9899 0.4272 0.188 Uiso 1 1 d . U . C 2
H11D_b H 0.3441 0.7366 0.3940 0.188 Uiso 1 1 d . U . D 2
O1A_a O 0.4307(8) 1.0208(14) 0.5024(7) 0.152(3) Uani 0.65 1 d D U P E 1
H1OA_a H 0.4846 1.0299 0.4848 0.228 Uiso 0.65 1 calc R U P E 1
O1B_b O 0.4747(7) 0.845(6) 0.5024(13) 0.177(7) Uani 0.35 1 d D U P E 2
H1OB_b H 0.4848 0.8603 0.5583 0.265 Uiso 0.35 1 calc R U P E 2
N3 N 0.5451(2) 0.6979(6) 0.7626(2) 0.0681(8) Uani 1 1 d . . . . .
N2 N 0.5367(2) 0.4622(6) 0.75587(18) 0.0567(6) Uani 1 1 d . . . . .
C4 C 0.6379(2) 0.3626(6) 0.78241(18) 0.0510(6) Uani 1 1 d . . . . .
H4 H 0.6547 0.2034 0.7848 0.061 Uiso 1 1 calc R U . . .
N4 N 0.6508(2) 0.7496(6) 0.7924(2) 0.0640(7) Uani 1 1 d . . . . .
C61 C 0.8325(2) 0.5484(6) 0.83627(18) 0.0521(6) Uani 1 1 d . . . . .
C31 C 0.3921(2) 0.2848(7) 0.8098(2) 0.0574(7) Uani 1 1 d . . . . .
C5 C 0.7107(2) 0.5472(7) 0.80507(18) 0.0509(6) Uani 1 1 d . . . . .
C62 C 0.8920(3) 0.7370(7) 0.8870(2) 0.0607(7) Uani 1 1 d . . . . .
H62 H 0.8545 0.8629 0.9015 0.073 Uiso 1 1 calc R U . . .
C66 C 0.8902(3) 0.3612(7) 0.8159(2) 0.0605(7) Uani 1 1 d . . . . .
H66 H 0.8515 0.2333 0.7825 0.073 Uiso 1 1 calc R U . . .
C2 C 0.4283(2) 0.3427(7) 0.7267(2) 0.0590(7) Uani 1 1 d . . . . .
H2 H 0.4357 0.1949 0.6962 0.071 Uiso 1 1 calc R U . . .
N1 N 0.3729(4) 0.5539(13) 0.5753(2) 0.1144(17) Uani 1 1 d . . . . .
C1 C 0.3410(3) 0.4931(9) 0.6554(2) 0.0736(10) Uani 1 1 d . . . . .
H1A H 0.2713 0.4079 0.6343 0.088 Uiso 1 1 calc R U . . .
H1B H 0.3293 0.6360 0.6855 0.088 Uiso 1 1 calc R U . . .
C36 C 0.4161(3) 0.4271(9) 0.8873(2) 0.0768(11) Uani 1 1 d . . . . .
H36 H 0.4578 0.5624 0.8904 0.092 Uiso 1 1 calc R U . . .
C12 C 0.1891(4) 0.6166(7) 0.4571(2) 0.0766(11) Uani 1 1 d . . . . .
C64 C 1.0629(3) 0.5534(9) 0.8948(3) 0.0729(9) Uani 1 1 d . . . . .
H64 H 1.1399 0.5558 0.9141 0.087 Uiso 1 1 calc R U . . .
C65 C 1.0053(3) 0.3640(8) 0.8451(3) 0.0696(9) Uani 1 1 d . . . . .
H65 H 1.0435 0.2384 0.8312 0.084 Uiso 1 1 calc R U . . .
C63 C 1.0065(3) 0.7384(8) 0.9159(3) 0.0715(9) Uani 1 1 d . . . . .
H63 H 1.0455 0.8653 0.9497 0.086 Uiso 1 1 calc R U . . .
C35 C 0.3796(4) 0.3727(12) 0.9600(3) 0.0920(14) Uani 1 1 d . . . . .
H35 H 0.3976 0.4699 1.0121 0.110 Uiso 1 1 calc R U . . .
C10 C 0.2969(4) 0.7265(11) 0.5129(3) 0.0966(14) Uani 1 1 d D . . . .
H10 H 0.2816 0.8497 0.5520 0.116 Uiso 1 1 calc R U . . .
C32 C 0.3287(4) 0.0903(9) 0.8066(3) 0.0874(11) Uani 1 1 d . . . . .
H32 H 0.3108 -0.0080 0.7548 0.105 Uiso 1 1 calc R U . . .
C34 C 0.3166(4) 0.1757(12) 0.9562(3) 0.0968(16) Uani 1 1 d . . . . .
H34 H 0.2922 0.1381 1.0057 0.116 Uiso 1 1 calc R U . . .
C33 C 0.2903(4) 0.0372(12) 0.8799(4) 0.1058(16) Uani 1 1 d . . . . .
H33 H 0.2462 -0.0947 0.8762 0.127 Uiso 1 1 calc R U . . .
C17 C 0.1834(6) 0.4161(10) 0.4078(4) 0.1117(18) Uani 1 1 d . . . . .
H17 H 0.2483 0.3374 0.4112 0.134 Uiso 1 1 calc R U . . .
C13 C 0.0912(6) 0.7261(11) 0.4485(4) 0.1106(17) Uani 1 1 d . . . . .
H13 H 0.0912 0.8657 0.4802 0.133 Uiso 1 1 calc R U . . .
C14 C -0.0100(7) 0.627(2) 0.3914(8) 0.150(3) Uani 1 1 d . . . . .
H14 H -0.0766 0.7028 0.3852 0.180 Uiso 1 1 calc R U . . .
C16 C 0.0822(11) 0.3271(17) 0.3523(5) 0.151(3) Uani 1 1 d . . . . .
H16 H 0.0800 0.1909 0.3179 0.181 Uiso 1 1 calc R U . . .
C15 C -0.0100(10) 0.432(3) 0.3476(6) 0.162(4) Uani 1 1 d . . . . .
H15 H -0.0772 0.3646 0.3123 0.194 Uiso 1 1 calc R U . . .
H1N H 0.450(7) 0.609(19) 0.607(7) 0.18(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 O1A_a 1.4208(14) . ?
C11 O1B_b 1.4214(15) . ?
C11 C10 1.545(6) . ?
N3 N4 1.308(4) . ?
N3 N2 1.348(4) . ?
N2 C4 1.346(4) . ?
N2 C2 1.473(4) . ?
C4 C5 1.370(4) . ?
N4 C5 1.362(4) . ?
C61 C66 1.389(4) . ?
C61 C62 1.391(4) . ?
C61 C5 1.470(4) . ?
C31 C32 1.365(5) . ?
C31 C36 1.377(5) . ?
C31 C2 1.520(4) . ?
C62 C63 1.381(5) . ?
C66 C65 1.389(5) . ?
C2 C1 1.532(5) . ?
N1 C1 1.449(4) . ?
N1 C10 1.481(7) . ?
C36 C35 1.369(5) . ?
C12 C17 1.355(6) . ?
C12 C13 1.365(7) . ?
C12 C10 1.494(7) . ?
C64 C63 1.374(6) . ?
C64 C65 1.381(6) . ?
C35 C34 1.372(8) . ?
C32 C33 1.391(6) . ?
C34 C33 1.348(9) . ?
C17 C16 1.384(11) . ?
C13 C14 1.412(12) . ?
C14 C15 1.299(15) . ?
C16 C15 1.302(14) . ?

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_a C11 C10 110.6(6) . . ?
O1B_b C11 C10 109.8(9) . . ?
N4 N3 N2 107.3(3) . . ?
C4 N2 N3 110.6(3) . . ?
C4 N2 C2 127.6(3) . . ?
N3 N2 C2 121.8(3) . . ?
N2 C4 C5 104.9(3) . . ?
N3 N4 C5 109.1(3) . . ?
C66 C61 C62 118.9(3) . . ?
C66 C61 C5 120.6(3) . . ?
C62 C61 C5 120.5(3) . . ?
C32 C31 C36 118.0(3) . . ?
C32 C31 C2 119.3(3) . . ?
C36 C31 C2 122.7(3) . . ?
N4 C5 C4 108.1(2) . . ?
N4 C5 C61 121.9(3) . . ?
C4 C5 C61 130.0(3) . . ?
C63 C62 C61 120.4(3) . . ?
C65 C66 C61 120.3(3) . . ?
N2 C2 C31 111.5(2) . . ?
N2 C2 C1 110.2(3) . . ?
C31 C2 C1 110.8(2) . . ?
C1 N1 C10 112.8(4) . . ?
N1 C1 C2 112.5(3) . . ?
C35 C36 C31 121.1(5) . . ?
C17 C12 C13 117.0(5) . . ?
C17 C12 C10 122.4(5) . . ?
C13 C12 C10 120.5(5) . . ?
C63 C64 C65 120.0(3) . . ?
C64 C65 C66 119.9(3) . . ?
C64 C63 C62 120.3(3) . . ?
C36 C35 C34 120.3(5) . . ?
N1 C10 C12 111.7(5) . . ?
N1 C10 C11 107.5(5) . . ?
C12 C10 C11 113.5(4) . . ?
C31 C32 C33 120.8(5) . . ?
C33 C34 C35 119.3(4) . . ?
C34 C33 C32 120.5(5) . . ?
C12 C17 C16 120.8(7) . . ?
C12 C13 C14 120.1(7) . . ?
C15 C14 C13 119.9(9) . . ?
C15 C16 C17 120.8(8) . . ?
C14 C15 C16 121.3(10) . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.043

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 2501476'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.76272(5)
_cell_length_b                   12.83000(10)
_cell_length_c                   17.79960(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1316.026(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    10041
_cell_measurement_theta_min      3.3830
_cell_measurement_theta_max      75.8060

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_min  0.74683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.422
_oxdiff_exptl_absorpt_empirical_full_max 1.382
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12327
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.248
_diffrn_reflns_theta_max         76.676
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2513
_reflns_number_gt                2472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_max     0.881
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0289P)²+0.2200P] 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
_refine_ls_extinction_coef       0.0043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2513
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.06603(17) 0.67684(8) 0.93733(6) 0.0201(2) Uani 1 1 d . . . . .
N1 N -0.2762(2) 0.84296(9) 0.91032(6) 0.0179(3) Uani 1 1 d . . . . .
C15 C -0.3136(3) 0.34984(12) 0.83765(8) 0.0223(3) Uani 1 1 d . . . . .
H15 H -0.3437 0.2818 0.8189 0.027 Uiso 1 1 calc R U . . .
C17 C -0.4383(2) 0.50259(11) 0.90532(8) 0.0195(3) Uani 1 1 d . . . . .
H17 H -0.5568 0.5391 0.9314 0.023 Uiso 1 1 calc R U . . .
C12 C -0.2215(2) 0.54865(11) 0.89587(8) 0.0168(3) Uani 1 1 d . . . . .
C5 C -0.4733(3) 1.05902(11) 0.94277(8) 0.0207(3) Uani 1 1 d . . . . .
H5 H -0.3679 1.0370 0.9806 0.025 Uiso 1 1 calc R U . . .
C14 C -0.0996(3) 0.39642(11) 0.82606(8) 0.0207(3) Uani 1 1 d . . . . .
H14 H 0.0164 0.3607 0.7982 0.025 Uiso 1 1 calc R U . . .
C11 C -0.1752(2) 0.65600(11) 0.92906(8) 0.0176(3) Uani 1 1 d . . . . .
H11 H -0.2514 0.6606 0.9794 0.021 Uiso 1 1 calc R U . . .
C10 C -0.2804(3) 0.73806(11) 0.87746(8) 0.0193(3) Uani 1 1 d . . . . .
H10A H -0.1935 0.7388 0.8295 0.023 Uiso 1 1 calc R U . . .
H10B H -0.4430 0.7187 0.8662 0.023 Uiso 1 1 calc R U . . .
C13 C -0.0531(2) 0.49547(11) 0.85500(7) 0.0182(3) Uani 1 1 d . . . . .
H13 H 0.0943 0.5267 0.8467 0.022 Uiso 1 1 calc R U . . .
C7 C -0.7922(3) 1.16757(11) 0.90451(9) 0.0223(3) Uani 1 1 d . . . . .
H7 H -0.9073 1.2180 0.9163 0.027 Uiso 1 1 calc R U . . .
C9 C -0.6125(3) 1.05127(11) 0.81589(8) 0.0204(3) Uani 1 1 d . . . . .
H9 H -0.6023 1.0243 0.7663 0.024 Uiso 1 1 calc R U . . .
C2 C -0.3030(3) 0.92706(11) 0.85337(8) 0.0195(3) Uani 1 1 d . . . . .
H2 H -0.3138 0.9015 0.8004 0.023 Uiso 1 1 calc R U . . .
C4 C -0.4615(2) 1.01495(11) 0.87106(8) 0.0180(3) Uani 1 1 d . . . . .
C6 C -0.6369(3) 1.13438(12) 0.95916(8) 0.0228(3) Uani 1 1 d . . . . .
H6 H -0.6432 1.1637 1.0081 0.027 Uiso 1 1 calc R U . . .
C8 C -0.7779(3) 1.12659(11) 0.83256(9) 0.0228(3) Uani 1 1 d . . . . .
H8 H -0.8815 1.1500 0.7946 0.027 Uiso 1 1 calc R U . . .
C3 C -0.0755(3) 0.90731(12) 0.88977(8) 0.0214(3) Uani 1 1 d . . . . .
H3B H 0.0478 0.8746 0.8590 0.026 Uiso 1 1 calc R U . . .
H3A H -0.0197 0.9589 0.9270 0.026 Uiso 1 1 calc R U . . .
C16 C -0.4834(3) 0.40366(11) 0.87692(8) 0.0223(3) Uani 1 1 d . . . . .
H16 H -0.6313 0.3728 0.8845 0.027 Uiso 1 1 calc R U . . .
H1 H 0.105(4) 0.6619(17) 0.9851(12) 0.046(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.4235(17) . ?
N1 C3 1.4675(19) . ?
N1 C10 1.4676(17) . ?
N1 C2 1.4886(18) . ?
C15 C14 1.386(2) . ?
C15 C16 1.386(2) . ?
C17 C16 1.391(2) . ?
C17 C12 1.3924(19) . ?
C12 C13 1.3919(19) . ?
C12 C11 1.522(2) . ?
C5 C6 1.382(2) . ?
C5 C4 1.398(2) . ?
C14 C13 1.397(2) . ?
C11 C10 1.523(2) . ?
C7 C8 1.387(2) . ?
C7 C6 1.389(2) . ?
C9 C8 1.390(2) . ?
C9 C4 1.392(2) . ?
C2 C3 1.484(2) . ?
C2 C4 1.485(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
C3 N1 C10 115.44(11) . . ?
C3 N1 C2 60.27(9) . . ?
C10 N1 C2 113.05(11) . . ?
C14 C15 C16 119.22(14) . . ?
C16 C17 C12 120.73(14) . . ?
C13 C12 C17 118.74(13) . . ?
C13 C12 C11 121.62(12) . . ?
C17 C12 C11 119.63(12) . . ?
C6 C5 C4 120.61(14) . . ?
C15 C14 C13 120.53(14) . . ?
O1 C11 C12 112.40(11) . . ?
O1 C11 C10 108.73(12) . . ?
C12 C11 C10 108.77(11) . . ?
N1 C10 C11 112.77(11) . . ?
C12 C13 C14 120.32(13) . . ?
C8 C7 C6 119.51(14) . . ?
C8 C9 C4 120.72(13) . . ?
C3 C2 C4 125.48(13) . . ?
C3 C2 N1 59.16(9) . . ?
C4 C2 N1 118.01(11) . . ?
C9 C4 C5 118.58(13) . . ?
C9 C4 C2 119.27(13) . . ?
C5 C4 C2 122.06(13) . . ?
C5 C6 C7 120.41(14) . . ?
C7 C8 C9 120.10(14) . . ?
N1 C3 C2 60.57(9) . . ?
C15 C16 C17 120.41(14) . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.038

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 2501475'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01493 Ang.
RESPONSE: very small crystals of poor quality, disordered structure
;
_vrf_PLAT415_shelx               
;
PROBLEM: Short Inter D-H..H-X       H1AN     ..H5A1     .       1.91 Ang.
RESPONSE:  used constrains for H positions because of crystal structure disorder (standard HFIX instruction in ShelxL)on 
;
# Added during the CSD deposition process: Sunday 09 November 2025 11:05 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 F3 N4 O'
_chemical_formula_weight         418.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   15.3455(4)
_cell_length_b                   5.6711(2)
_cell_length_c                   25.6255(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.668(3)
_cell_angle_gamma                90
_cell_volume                     2198.41(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11026
_cell_measurement_theta_min      2.8960
_cell_measurement_theta_max      71.9910

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.816
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.72214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.411
_oxdiff_exptl_absorpt_empirical_full_max 3.342
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            36917
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         68.995
_diffrn_reflns_theta_full        67.684
_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 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             7633
_reflns_number_gt                5295
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.872

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0567P)²+1.9837P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(13)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         7633
_refine_ls_number_parameters     603
_refine_ls_number_restraints     110
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2415
_refine_ls_wR_factor_gt          0.2317
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_restrained_S_all      1.294
_refine_ls_shift/su_max          0.004
_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
F11A_a F 1.366(2) -0.091(4) 0.4359(10) 0.191(8) Uani 0.7 1 d . U P A 1
F12A_a F 1.4275(13) 0.206(7) 0.4722(7) 0.180(8) Uani 0.7 1 d . U P A 1
F13A_a F 1.3046(12) 0.239(6) 0.4216(8) 0.166(6) Uani 0.7 1 d . U P A 1
F22A_b F 1.377(4) 0.355(7) 0.458(2) 0.161(14) Uani 0.3 1 d . U P A 2
F23A_b F 1.314(3) 0.047(12) 0.4172(14) 0.135(12) Uani 0.3 1 d . U P A 2
F21A_b F 1.430(3) 0.015(10) 0.4647(19) 0.139(12) Uani 0.3 1 d . U P A 2
F11B_c F 0.066(2) 0.886(10) 1.0276(13) 0.168(15) Uani 0.49(5) 1 d . U P B 3
F12B_c F 0.192(3) 0.882(9) 1.0756(8) 0.171(14) Uani 0.49(5) 1 d . U P B 3
F13B_c F 0.140(4) 1.199(6) 1.040(2) 0.177(15) Uani 0.49(5) 1 d . U P B 3
F21B_d F 0.138(4) 0.765(7) 1.0588(17) 0.190(16) Uani 0.51(5) 1 d . U P B 4
F22B_d F 0.071(3) 1.055(12) 1.0190(14) 0.192(16) Uani 0.51(5) 1 d . U P B 4
F23B_d F 0.192(3) 1.110(10) 1.0649(12) 0.175(15) Uani 0.51(5) 1 d . U P B 4
N2A N 1.1402(4) 0.0209(13) 0.7164(3) 0.0659(17) Uani 1 1 d . . . . .
N1A N 0.9537(4) 0.1053(12) 0.7372(2) 0.0679(17) Uani 1 1 d . . . . .
H1AN H 0.9475 -0.0317 0.7505 0.081 Uiso 1 1 calc R U . . .
N2B N 0.3537(4) 0.7737(15) 0.7755(3) 0.0737(18) Uani 1 1 d . . . . .
N3A N 1.1458(4) -0.2076(13) 0.7081(3) 0.0761(19) Uani 1 1 d . . . . .
N4B N 0.3034(5) 0.5392(14) 0.8278(3) 0.085(2) Uani 1 1 d . . . . .
N3B N 0.3374(5) 0.5472(14) 0.7837(3) 0.085(2) Uani 1 1 d . . . . .
C7B C 0.3317(5) 0.9136(15) 0.8133(3) 0.067(2) Uani 1 1 d . . . . .
H7B H 0.3369 1.0767 0.8162 0.080 Uiso 1 1 calc R U . . .
N1B N 0.5415(4) 0.7353(14) 0.7634(3) 0.083(2) Uani 1 1 d . . . . .
H1BN H 0.5310 0.5928 0.7527 0.099 Uiso 1 1 calc R U . . .
C12A C 0.9154(5) 0.1565(15) 0.6400(3) 0.064(2) Uani 1 1 d . . . . .
C10A C 0.8897(5) 0.1986(16) 0.6939(3) 0.070(2) Uani 1 1 d . . . . .
H10A H 0.8808 0.3674 0.6992 0.084 Uiso 1 1 calc R U . . .
O1A O 0.7711(5) 0.100(2) 0.7426(3) 0.140(3) Uani 1 1 d . U . . .
H1AO H 0.7675 -0.0278 0.7572 0.209 Uiso 1 1 calc R U . . .
C7A C 1.1658(5) 0.1460(15) 0.6768(3) 0.067(2) Uani 1 1 d . . . . .
H7A H 1.1679 0.3090 0.6731 0.080 Uiso 1 1 calc R U . . .
C6B C 0.2997(5) 0.7590(17) 0.8471(3) 0.071(2) Uani 1 1 d . . . . .
C17A C 0.9558(5) -0.0483(15) 0.6285(3) 0.076(2) Uani 1 1 d . . . . .
H17A H 0.9708 -0.1617 0.6547 0.091 Uiso 1 1 calc R U . . .
C61A C 1.2262(5) 0.0064(15) 0.5944(3) 0.070(2) Uani 1 1 d . . . . .
C1A C 1.0290(4) 0.2564(15) 0.7571(3) 0.067(2) Uani 1 1 d . . . . .
H1A H 1.0338 0.3758 0.7300 0.080 Uiso 1 1 calc R U . . .
C61B C 0.2622(5) 0.8156(16) 0.8952(3) 0.069(2) Uani 1 1 d . . . . .
C1B C 0.4859(5) 0.9321(16) 0.7418(3) 0.070(2) Uani 1 1 d . . . . .
H1B H 0.4885 1.0512 0.7697 0.084 Uiso 1 1 calc R U . . .
C13A C 0.8913(5) 0.3179(18) 0.5999(3) 0.083(3) Uani 1 1 d . . . . .
H13A H 0.8635 0.4572 0.6070 0.100 Uiso 1 1 calc R U . . .
C2B C 0.3903(5) 0.8486(18) 0.7281(3) 0.079(3) Uani 1 1 d . . . . .
H21B H 0.3543 0.9755 0.7106 0.095 Uiso 1 1 calc R U . . .
H22B H 0.3872 0.7175 0.7035 0.095 Uiso 1 1 calc R U . . .
C15A C 0.9495(6) 0.073(2) 0.5394(4) 0.095(3) Uani 1 1 d . . . . .
H15A H 0.9610 0.0432 0.5055 0.114 Uiso 1 1 calc R U . . .
C66A C 1.2812(6) -0.1693(18) 0.5794(4) 0.084(3) Uani 1 1 d . . . . .
H66A H 1.2908 -0.3085 0.5987 0.101 Uiso 1 1 calc R U . . .
C64A C 1.3064(6) 0.069(2) 0.5062(4) 0.090(3) Uani 1 1 d . . . . .
C2A C 1.1149(5) 0.1085(17) 0.7653(3) 0.073(2) Uani 1 1 d . . . . .
H22A H 1.1628 0.2044 0.7838 0.087 Uiso 1 1 calc R U . . .
H21A H 1.1074 -0.0248 0.7879 0.087 Uiso 1 1 calc R U . . .
C3A C 1.0221(5) 0.3845(18) 0.8089(3) 0.081(2) Uani 1 1 d . . . . .
H3A H 1.0746 0.4848 0.8170 0.097 Uiso 1 1 calc R U . . .
C8A C 1.3504(11) 0.109(4) 0.4589(6) 0.128(4) Uani 1 1 d . U . . .
C62A C 1.2112(6) 0.2056(16) 0.5645(4) 0.081(2) Uani 1 1 d . . . . .
H62A H 1.1738 0.3212 0.5740 0.097 Uiso 1 1 calc R U . . .
C3B C 0.5187(7) 1.048(2) 0.6946(4) 0.099(3) Uani 1 1 d . . . . .
H00U H 0.5762 1.1185 0.7087 0.119 Uiso 1 1 calc R U . . .
C66B C 0.2834(6) 1.0144(19) 0.9233(4) 0.093(3) Uani 1 1 d . . . . .
H66B H 0.3234 1.1193 0.9125 0.112 Uiso 1 1 calc R U . . .
C12B C 0.5900(7) 0.823(2) 0.8581(4) 0.101(3) Uani 1 1 d . . . . .
C62B C 0.2049(6) 0.6527(18) 0.9129(4) 0.087(3) Uani 1 1 d . . . . .
H62B H 0.1920 0.5102 0.8953 0.104 Uiso 1 1 calc R U . . .
C65A C 1.3214(6) -0.133(2) 0.5352(4) 0.095(3) Uani 1 1 d . . . . .
H65A H 1.3588 -0.2477 0.5254 0.114 Uiso 1 1 calc R U . . .
C64B C 0.1885(6) 0.913(2) 0.9839(4) 0.090(3) Uani 1 1 d . . . . .
C11A C 0.8023(6) 0.064(3) 0.6933(4) 0.109(3) Uani 1 1 d . U . . .
H11A H 0.7583 0.1197 0.6643 0.131 Uiso 1 1 calc R U . . .
H12A H 0.8115 -0.1031 0.6881 0.131 Uiso 1 1 calc R U . . .
C16A C 0.9743(6) -0.0870(19) 0.5786(4) 0.088(3) Uani 1 1 d . . . . .
H16A H 1.0039 -0.2234 0.5716 0.105 Uiso 1 1 calc R U . . .
C65B C 0.2470(7) 1.066(2) 0.9680(4) 0.102(3) Uani 1 1 d . . . . .
H65B H 0.2624 1.2045 0.9869 0.122 Uiso 1 1 calc R U . . .
C63B C 0.1679(7) 0.708(2) 0.9570(4) 0.106(4) Uani 1 1 d . . . . .
H63B H 0.1283 0.6037 0.9684 0.128 Uiso 1 1 calc R U . . .
C14A C 0.9077(6) 0.276(2) 0.5495(4) 0.090(3) Uani 1 1 d . . . . .
H14A H 0.8904 0.3848 0.5226 0.108 Uiso 1 1 calc R U . . .
O1B O 0.7088(6) 0.570(2) 0.7561(4) 0.158(3) Uani 1 1 d . U . . .
H1BO H 0.7031 0.4321 0.7465 0.236 Uiso 1 1 calc R U . . .
C63A C 1.2506(6) 0.239(2) 0.5202(4) 0.099(3) Uani 1 1 d . . . . .
H63A H 1.2394 0.3756 0.5000 0.119 Uiso 1 1 calc R U . . .
C8B C 0.1468(13) 0.971(4) 1.0319(6) 0.133(5) Uani 1 1 d . U . . .
C10B C 0.6147(6) 0.795(2) 0.8038(4) 0.099(3) Uani 1 1 d . . . . .
H10B H 0.6416 0.9416 0.7940 0.119 Uiso 1 1 calc R U . . .
C5A C 0.9427(7) 0.5472(19) 0.8035(4) 0.111(3) Uani 1 1 d . . . . .
H5A1 H 0.9427 0.6500 0.7738 0.166 Uiso 1 1 calc R U . . .
H5A2 H 0.9456 0.6396 0.8352 0.166 Uiso 1 1 calc R U . . .
H5A3 H 0.8895 0.4550 0.7983 0.166 Uiso 1 1 calc R U . . .
C17B C 0.5320(7) 0.668(2) 0.8749(4) 0.113(4) Uani 1 1 d . . . . .
H17B H 0.5075 0.5503 0.8516 0.135 Uiso 1 1 calc R U . . .
C4A C 1.0236(7) 0.2189(19) 0.8559(3) 0.095(3) Uani 1 1 d . . . . .
H41A H 0.9719 0.1207 0.8501 0.143 Uiso 1 1 calc R U . . .
H42A H 1.0243 0.3099 0.8876 0.143 Uiso 1 1 calc R U . . .
H43A H 1.0755 0.1218 0.8596 0.143 Uiso 1 1 calc R U . . .
C13B C 0.6237(10) 1.002(3) 0.8927(6) 0.143(5) Uani 1 1 d . . . . .
H13B H 0.6623 1.1119 0.8823 0.172 Uiso 1 1 calc R U . . .
C14B C 0.5995(11) 1.018(3) 0.9443(6) 0.144(5) Uani 1 1 d . . . . .
H14B H 0.6217 1.1358 0.9682 0.173 Uiso 1 1 calc R U . . .
C4B C 0.4585(9) 1.254(2) 0.6721(5) 0.128(4) Uani 1 1 d . . . . .
H01M H 0.4049 1.1927 0.6518 0.192 Uiso 1 1 calc R U . . .
H01N H 0.4884 1.3494 0.6497 0.192 Uiso 1 1 calc R U . . .
H01O H 0.4444 1.3484 0.7006 0.192 Uiso 1 1 calc R U . . .
C16B C 0.5079(9) 0.675(3) 0.9241(5) 0.143(5) Uani 1 1 d . U . . .
H16B H 0.4699 0.5635 0.9346 0.171 Uiso 1 1 calc R U . . .
C15B C 0.5419(12) 0.851(4) 0.9562(6) 0.157(6) Uani 1 1 d . U . . .
H15B H 0.5248 0.8597 0.9893 0.189 Uiso 1 1 calc R U . . .
C11B C 0.6822(6) 0.595(3) 0.8063(4) 0.120(4) Uani 1 1 d . U . . .
H11B H 0.7332 0.6299 0.8331 0.144 Uiso 1 1 calc R U . . .
H12B H 0.6561 0.4488 0.8160 0.144 Uiso 1 1 calc R U . . .
C5B C 0.5341(8) 0.888(2) 0.6520(4) 0.126(4) Uani 1 1 d . . . . .
H01T H 0.5786 0.7751 0.6657 0.189 Uiso 1 1 calc R U . . .
H01U H 0.5536 0.9774 0.6243 0.189 Uiso 1 1 calc R U . . .
H01V H 0.4802 0.8077 0.6381 0.189 Uiso 1 1 calc R U . . .
N4A N 1.1760(4) -0.2378(12) 0.6637(3) 0.0730(18) Uani 1 1 d . . . . .
C6A C 1.1881(5) -0.0238(15) 0.6434(3) 0.065(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F11A_a C8A 1.32(2) . ?
F12A_a C8A 1.30(2) . ?
F13A_a C8A 1.32(2) . ?
F22A_b C8A 1.45(4) . ?
F23A_b C8A 1.17(3) . ?
F21A_b C8A 1.32(4) . ?
F11B_c C8B 1.32(3) . ?
F12B_c C8B 1.32(3) . ?
F13B_c C8B 1.31(3) . ?
F21B_d C8B 1.38(3) . ?
F22B_d C8B 1.25(3) . ?
F23B_d C8B 1.27(3) . ?
N2A N3A 1.319(9) . ?
N2A C7A 1.350(10) . ?
N2A C2A 1.459(10) . ?
N1A C10A 1.453(9) . ?
N1A C1A 1.459(9) . ?
N1A H1AN 0.8600 . ?
N2B N3B 1.333(11) . ?
N2B C7B 1.339(10) . ?
N2B C2B 1.484(10) . ?
N3A N4A 1.310(9) . ?
N4B N3B 1.322(10) . ?
N4B C6B 1.345(12) . ?
C7B C6B 1.379(11) . ?
C7B H7B 0.9300 . ?
N1B C10B 1.434(10) . ?
N1B C1B 1.456(10) . ?
N1B H1BN 0.8600 . ?
C12A C17A 1.372(11) . ?
C12A C13A 1.380(11) . ?
C12A C10A 1.516(10) . ?
C10A C11A 1.543(12) . ?
C10A H10A 0.9800 . ?
O1A C11A 1.436(11) . ?
O1A H1AO 0.8200 . ?
C7A C6A 1.370(10) . ?
C7A H7A 0.9300 . ?
C6B C61B 1.480(11) . ?
C17A C16A 1.374(12) . ?
C17A H17A 0.9300 . ?
C61A C62A 1.363(12) . ?
C61A C66A 1.401(12) . ?
C61A C6A 1.481(11) . ?
C1A C3A 1.533(11) . ?
C1A C2A 1.547(10) . ?
C1A H1A 0.9800 . ?
C61B C66B 1.348(13) . ?
C61B C62B 1.403(11) . ?
C1B C2B 1.526(11) . ?
C1B C3B 1.536(12) . ?
C1B H1B 0.9800 . ?
C13A C14A 1.379(12) . ?
C13A H13A 0.9300 . ?
C2B H21B 0.9700 . ?
C2B H22B 0.9700 . ?
C15A C16A 1.359(14) . ?
C15A C14A 1.365(14) . ?
C15A H15A 0.9300 . ?
C66A C65A 1.393(12) . ?
C66A H66A 0.9300 . ?
C64A C65A 1.365(14) . ?
C64A C63A 1.376(14) . ?
C64A C8A 1.499(15) . ?
C2A H22A 0.9700 . ?
C2A H21A 0.9700 . ?
C3A C5A 1.516(12) . ?
C3A C4A 1.525(12) . ?
C3A H3A 0.9800 . ?
C62A C63A 1.386(12) . ?
C62A H62A 0.9300 . ?
C3B C5B 1.469(14) . ?
C3B C4B 1.539(14) . ?
C3B H00U 0.9800 . ?
C66B C65B 1.389(13) . ?
C66B H66B 0.9300 . ?
C12B C17B 1.373(15) . ?
C12B C13B 1.389(18) . ?
C12B C10B 1.510(13) . ?
C62B C63B 1.384(13) . ?
C62B H62B 0.9300 . ?
C65A H65A 0.9300 . ?
C64B C63B 1.361(15) . ?
C64B C65B 1.361(14) . ?
C64B C8B 1.514(16) . ?
C11A H11A 0.9700 . ?
C11A H12A 0.9700 . ?
C16A H16A 0.9300 . ?
C65B H65B 0.9300 . ?
C63B H63B 0.9300 . ?
C14A H14A 0.9300 . ?
O1B C11B 1.422(11) . ?
O1B H1BO 0.8200 . ?
C63A H63A 0.9300 . ?
C10B C11B 1.530(15) . ?
C10B H10B 0.9800 . ?
C5A H5A1 0.9600 . ?
C5A H5A2 0.9600 . ?
C5A H5A3 0.9600 . ?
C17B C16B 1.372(15) . ?
C17B H17B 0.9300 . ?
C4A H41A 0.9600 . ?
C4A H42A 0.9600 . ?
C4A H43A 0.9600 . ?
C13B C14B 1.436(18) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.37(2) . ?
C14B H14B 0.9300 . ?
C4B H01M 0.9600 . ?
C4B H01N 0.9600 . ?
C4B H01O 0.9600 . ?
C16B C15B 1.34(2) . ?
C16B H16B 0.9300 . ?
C15B H15B 0.9300 . ?
C11B H11B 0.9700 . ?
C11B H12B 0.9700 . ?
C5B H01T 0.9600 . ?
C5B H01U 0.9600 . ?
C5B H01V 0.9600 . ?
N4A C6A 1.346(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
N3A N2A C7A 111.1(7) . . ?
N3A N2A C2A 120.5(7) . . ?
C7A N2A C2A 128.3(7) . . ?
C10A N1A C1A 116.5(6) . . ?
C10A N1A H1AN 121.7 . . ?
C1A N1A H1AN 121.8 . . ?
N3B N2B C7B 112.4(7) . . ?
N3B N2B C2B 120.8(8) . . ?
C7B N2B C2B 126.8(8) . . ?
N4A N3A N2A 108.1(7) . . ?
N3B N4B C6B 109.2(7) . . ?
N4B N3B N2B 106.2(7) . . ?
N2B C7B C6B 103.7(8) . . ?
N2B C7B H7B 128.2 . . ?
C6B C7B H7B 128.2 . . ?
C10B N1B C1B 115.6(8) . . ?
C10B N1B H1BN 122.2 . . ?
C1B N1B H1BN 122.2 . . ?
C17A C12A C13A 118.4(8) . . ?
C17A C12A C10A 121.6(7) . . ?
C13A C12A C10A 119.7(8) . . ?
N1A C10A C12A 113.2(6) . . ?
N1A C10A C11A 107.6(7) . . ?
C12A C10A C11A 105.8(7) . . ?
N1A C10A H10A 110.1 . . ?
C12A C10A H10A 110.1 . . ?
C11A C10A H10A 110.1 . . ?
C11A O1A H1AO 109.5 . . ?
N2A C7A C6A 103.7(7) . . ?
N2A C7A H7A 128.2 . . ?
C6A C7A H7A 128.2 . . ?
N4B C6B C7B 108.5(8) . . ?
N4B C6B C61B 123.6(8) . . ?
C7B C6B C61B 127.8(9) . . ?
C12A C17A C16A 120.5(9) . . ?
C12A C17A H17A 119.8 . . ?
C16A C17A H17A 119.8 . . ?
C62A C61A C66A 119.2(8) . . ?
C62A C61A C6A 121.3(8) . . ?
C66A C61A C6A 119.5(8) . . ?
N1A C1A C3A 114.4(6) . . ?
N1A C1A C2A 109.7(7) . . ?
C3A C1A C2A 108.6(6) . . ?
N1A C1A H1A 108.0 . . ?
C3A C1A H1A 108.0 . . ?
C2A C1A H1A 108.0 . . ?
C66B C61B C62B 119.1(8) . . ?
C66B C61B C6B 122.3(8) . . ?
C62B C61B C6B 118.6(8) . . ?
N1B C1B C2B 109.2(7) . . ?
N1B C1B C3B 112.4(7) . . ?
C2B C1B C3B 112.4(7) . . ?
N1B C1B H1B 107.5 . . ?
C2B C1B H1B 107.5 . . ?
C3B C1B H1B 107.5 . . ?
C14A C13A C12A 121.0(9) . . ?
C14A C13A H13A 119.5 . . ?
C12A C13A H13A 119.5 . . ?
N2B C2B C1B 112.4(6) . . ?
N2B C2B H21B 109.1 . . ?
C1B C2B H21B 109.1 . . ?
N2B C2B H22B 109.1 . . ?
C1B C2B H22B 109.1 . . ?
H21B C2B H22B 107.9 . . ?
C16A C15A C14A 120.3(9) . . ?
C16A C15A H15A 119.9 . . ?
C14A C15A H15A 119.9 . . ?
C65A C66A C61A 119.2(10) . . ?
C65A C66A H66A 120.4 . . ?
C61A C66A H66A 120.4 . . ?
C65A C64A C63A 120.1(9) . . ?
C65A C64A C8A 120.6(13) . . ?
C63A C64A C8A 119.3(13) . . ?
N2A C2A C1A 114.2(6) . . ?
N2A C2A H22A 108.7 . . ?
C1A C2A H22A 108.7 . . ?
N2A C2A H21A 108.7 . . ?
C1A C2A H21A 108.7 . . ?
H22A C2A H21A 107.6 . . ?
C5A C3A C4A 110.5(7) . . ?
C5A C3A C1A 112.5(7) . . ?
C4A C3A C1A 113.5(8) . . ?
C5A C3A H3A 106.6 . . ?
C4A C3A H3A 106.6 . . ?
C1A C3A H3A 106.6 . . ?
F12A_a C8A F13A_a 108(2) . . ?
F23A_b C8A F21A_b 106(4) . . ?
F12A_a C8A F11A_a 105(2) . . ?
F13A_a C8A F11A_a 106(2) . . ?
F23A_b C8A F22A_b 111(3) . . ?
F21A_b C8A F22A_b 98(3) . . ?
F23A_b C8A C64A 119(2) . . ?
F12A_a C8A C64A 111.5(14) . . ?
F13A_a C8A C64A 114.4(15) . . ?
F21A_b C8A C64A 113(2) . . ?
F11A_a C8A C64A 111.9(16) . . ?
F22A_b C8A C64A 108.7(19) . . ?
C61A C62A C63A 121.3(9) . . ?
C61A C62A H62A 119.4 . . ?
C63A C62A H62A 119.4 . . ?
C5B C3B C1B 115.8(10) . . ?
C5B C3B C4B 110.6(9) . . ?
C1B C3B C4B 111.4(8) . . ?
C5B C3B H00U 106.1 . . ?
C1B C3B H00U 106.1 . . ?
C4B C3B H00U 106.1 . . ?
C61B C66B C65B 121.6(9) . . ?
C61B C66B H66B 119.2 . . ?
C65B C66B H66B 119.2 . . ?
C17B C12B C13B 117.4(12) . . ?
C17B C12B C10B 119.9(11) . . ?
C13B C12B C10B 122.8(12) . . ?
C63B C62B C61B 118.7(10) . . ?
C63B C62B H62B 120.6 . . ?
C61B C62B H62B 120.6 . . ?
C64A C65A C66A 120.7(10) . . ?
C64A C65A H65A 119.7 . . ?
C66A C65A H65A 119.7 . . ?
C63B C64B C65B 120.2(9) . . ?
C63B C64B C8B 120.3(12) . . ?
C65B C64B C8B 119.5(12) . . ?
O1A C11A C10A 109.8(8) . . ?
O1A C11A H11A 109.7 . . ?
C10A C11A H11A 109.7 . . ?
O1A C11A H12A 109.7 . . ?
C10A C11A H12A 109.7 . . ?
H11A C11A H12A 108.2 . . ?
C15A C16A C17A 120.4(10) . . ?
C15A C16A H16A 119.8 . . ?
C17A C16A H16A 119.8 . . ?
C64B C65B C66B 119.2(10) . . ?
C64B C65B H65B 120.4 . . ?
C66B C65B H65B 120.4 . . ?
C64B C63B C62B 121.1(10) . . ?
C64B C63B H63B 119.5 . . ?
C62B C63B H63B 119.5 . . ?
C15A C14A C13A 119.3(9) . . ?
C15A C14A H14A 120.3 . . ?
C13A C14A H14A 120.3 . . ?
C11B O1B H1BO 109.5 . . ?
C64A C63A C62A 119.5(10) . . ?
C64A C63A H63A 120.2 . . ?
C62A C63A H63A 120.2 . . ?
F22B_d C8B F23B_d 109(3) . . ?
F13B_c C8B F12B_c 107(3) . . ?
F13B_c C8B F11B_c 106(3) . . ?
F12B_c C8B F11B_c 106(3) . . ?
F22B_d C8B F21B_d 106(3) . . ?
F23B_d C8B F21B_d 106(3) . . ?
F22B_d C8B C64B 112(2) . . ?
F23B_d C8B C64B 114.6(18) . . ?
F13B_c C8B C64B 113.4(19) . . ?
F12B_c C8B C64B 111.9(19) . . ?
F11B_c C8B C64B 111.8(19) . . ?
F21B_d C8B C64B 108(2) . . ?
N1B C10B C12B 113.7(8) . . ?
N1B C10B C11B 107.4(10) . . ?
C12B C10B C11B 108.1(8) . . ?
N1B C10B H10B 109.2 . . ?
C12B C10B H10B 109.2 . . ?
C11B C10B H10B 109.2 . . ?
C3A C5A H5A1 109.5 . . ?
C3A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C3A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C16B C17B C12B 123.9(14) . . ?
C16B C17B H17B 118.1 . . ?
C12B C17B H17B 118.1 . . ?
C3A C4A H41A 109.5 . . ?
C3A C4A H42A 109.5 . . ?
H41A C4A H42A 109.5 . . ?
C3A C4A H43A 109.5 . . ?
H41A C4A H43A 109.5 . . ?
H42A C4A H43A 109.5 . . ?
C12B C13B C14B 120.7(15) . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B H13B 119.7 . . ?
C15B C14B C13B 116.0(17) . . ?
C15B C14B H14B 122.0 . . ?
C13B C14B H14B 122.0 . . ?
C3B C4B H01M 109.5 . . ?
C3B C4B H01N 109.5 . . ?
H01M C4B H01N 109.5 . . ?
C3B C4B H01O 109.5 . . ?
H01M C4B H01O 109.5 . . ?
H01N C4B H01O 109.5 . . ?
C15B C16B C17B 116.7(16) . . ?
C15B C16B H16B 121.6 . . ?
C17B C16B H16B 121.6 . . ?
C16B C15B C14B 125.4(17) . . ?
C16B C15B H15B 117.3 . . ?
C14B C15B H15B 117.3 . . ?
O1B C11B C10B 109.3(9) . . ?
O1B C11B H11B 109.8 . . ?
C10B C11B H11B 109.8 . . ?
O1B C11B H12B 109.8 . . ?
C10B C11B H12B 109.8 . . ?
H11B C11B H12B 108.3 . . ?
C3B C5B H01T 109.5 . . ?
C3B C5B H01U 109.5 . . ?
H01T C5B H01U 109.5 . . ?
C3B C5B H01V 109.5 . . ?
H01T C5B H01V 109.5 . . ?
H01U C5B H01V 109.5 . . ?
N3A N4A C6A 108.1(7) . . ?
N4A C6A C7A 109.0(7) . . ?
N4A C6A C61A 122.2(7) . . ?
C7A C6A C61A 128.7(8) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 2501480'
loop_
_audit_author_name
_audit_author_address
'Rybarczyk-Pirek Agnieszka'
;Univeristy of Lodz
Poland
;
_audit_update_record             
;
2025-11-09 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N4 O'
_chemical_formula_weight         282.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.45000(10)
_cell_length_b                   8.09740(10)
_cell_length_c                   34.1450(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1506.85(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110.00(10)
_cell_measurement_reflns_used    10568
_cell_measurement_theta_min      5.5850
_cell_measurement_theta_max      76.5440

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.649
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.76571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.558
_oxdiff_exptl_absorpt_empirical_full_max 1.226
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14360
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         76.746
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2972
_reflns_number_gt                2895
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.914
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0363P)²+0.2675P] 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
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2972
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9212(2) 0.40570(13) 0.57646(3) 0.0218(2) Uani 1 1 d . . . . .
N32 N 0.3333(3) 0.85650(17) 0.64754(4) 0.0242(3) Uani 1 1 d . . . . .
N1 N 0.4186(2) 0.41650(16) 0.59702(4) 0.0183(3) Uani 1 1 d . . . . .
N31 N 0.4234(3) 0.72140(17) 0.63881(4) 0.0263(3) Uani 1 1 d . . . . .
C41 C 0.2705(3) 0.57635(18) 0.69896(4) 0.0192(3) Uani 1 1 d . . . . .
N33 N 0.2704(3) 0.98687(18) 0.65388(4) 0.0324(3) Uani 1 1 d . . . . .
C11 C 0.8150(3) 0.25496(18) 0.58881(4) 0.0173(3) Uani 1 1 d . . . . .
H11 H 0.8412 0.2416 0.6176 0.021 Uiso 1 1 calc R U . . .
C46 C 0.4471(3) 0.65148(19) 0.72240(5) 0.0239(3) Uani 1 1 d . . . . .
H46 H 0.5823 0.7063 0.7106 0.029 Uiso 1 1 calc R U . . .
C12 C 0.9139(3) 0.10391(18) 0.56777(4) 0.0177(3) Uani 1 1 d . . . . .
C45 C 0.4271(3) 0.6469(2) 0.76293(5) 0.0286(4) Uani 1 1 d . . . . .
H45 H 0.5479 0.6992 0.7787 0.034 Uiso 1 1 calc R U . . .
C42 C 0.0761(3) 0.4950(2) 0.71690(5) 0.0244(3) Uani 1 1 d . . . . .
H42 H -0.0449 0.4425 0.7012 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5390(3) 0.27000(18) 0.58059(4) 0.0178(3) Uani 1 1 d . . . . .
H10A H 0.5142 0.2704 0.5519 0.021 Uiso 1 1 calc R U . . .
H10B H 0.4564 0.1706 0.5911 0.021 Uiso 1 1 calc R U . . .
C44 C 0.2316(3) 0.5663(2) 0.78045(5) 0.0287(4) Uani 1 1 d . . . . .
H44 H 0.2177 0.5637 0.8082 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4271(3) 0.42502(19) 0.63975(4) 0.0208(3) Uani 1 1 d . . . . .
H2A H 0.6001 0.4308 0.6485 0.025 Uiso 1 1 calc R U . . .
H2B H 0.3533 0.3237 0.6509 0.025 Uiso 1 1 calc R U . . .
C43 C 0.0563(3) 0.4894(2) 0.75736(5) 0.0289(4) Uani 1 1 d . . . . .
H43 H -0.0773 0.4330 0.7692 0.035 Uiso 1 1 calc R U . . .
C3 C 0.2888(3) 0.57563(18) 0.65472(4) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.1193 0.5745 0.6435 0.024 Uiso 1 1 calc R U . . .
C13 C 1.0411(3) 0.11625(19) 0.53256(4) 0.0212(3) Uani 1 1 d . . . . .
H13 H 1.0678 0.2216 0.5211 0.025 Uiso 1 1 calc R U . . .
C16 C 0.9550(3) -0.19293(19) 0.56476(5) 0.0273(4) Uani 1 1 d . . . . .
H16 H 0.9222 -0.2988 0.5756 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8715(3) -0.05197(19) 0.58350(5) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.7839 -0.0619 0.6074 0.027 Uiso 1 1 calc R U . . .
C15 C 1.0871(3) -0.1789(2) 0.53006(5) 0.0281(4) Uani 1 1 d . . . . .
H15 H 1.1480 -0.2750 0.5174 0.034 Uiso 1 1 calc R U . . .
C14 C 1.1295(3) -0.0247(2) 0.51400(5) 0.0255(3) Uani 1 1 d . . . . .
H14 H 1.2193 -0.0150 0.4903 0.031 Uiso 1 1 calc R U . . .
H1O H 1.081(5) 0.408(3) 0.5814(7) 0.044(6) Uiso 1 1 d . . . . .
H1N H 0.489(4) 0.507(3) 0.5870(5) 0.026(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.4150(18) . ?
O1 H1O 0.89(3) . ?
N32 N33 1.131(2) . ?
N32 N31 1.236(2) . ?
N1 C2 1.4613(19) . ?
N1 C10 1.4673(19) . ?
N1 H1N 0.90(2) . ?
N31 C3 1.4921(19) . ?
C41 C42 1.390(2) . ?
C41 C46 1.392(2) . ?
C41 C3 1.514(2) . ?
C11 C12 1.517(2) . ?
C11 C10 1.5350(19) . ?
C11 H11 1.0000 . ?
C46 C45 1.389(2) . ?
C46 H46 0.9500 . ?
C12 C17 1.391(2) . ?
C12 C13 1.391(2) . ?
C45 C44 1.386(3) . ?
C45 H45 0.9500 . ?
C42 C43 1.386(2) . ?
C42 H42 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C44 C43 1.387(2) . ?
C44 H44 0.9500 . ?
C2 C3 1.522(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C43 H43 0.9500 . ?
C3 H3 1.0000 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C16 C17 1.385(2) . ?
C16 C15 1.391(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C15 C14 1.383(2) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 H1O 111.4(15) . . ?
N33 N32 N31 173.29(17) . . ?
C2 N1 C10 113.93(12) . . ?
C2 N1 H1N 109.2(12) . . ?
C10 N1 H1N 109.0(12) . . ?
N32 N31 C3 114.65(13) . . ?
C42 C41 C46 118.74(14) . . ?
C42 C41 C3 119.21(13) . . ?
C46 C41 C3 122.01(14) . . ?
O1 C11 C12 114.15(12) . . ?
O1 C11 C10 106.11(12) . . ?
C12 C11 C10 108.99(12) . . ?
O1 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
C45 C46 C41 120.48(15) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C17 C12 C13 118.79(13) . . ?
C17 C12 C11 119.31(13) . . ?
C13 C12 C11 121.88(13) . . ?
C44 C45 C46 120.21(16) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C43 C42 C41 120.95(15) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
N1 C10 C11 115.64(12) . . ?
N1 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
N1 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C45 C44 C43 119.73(15) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
N1 C2 C3 110.94(12) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
C42 C43 C44 119.88(15) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
N31 C3 C41 113.11(12) . . ?
N31 C3 C2 105.54(12) . . ?
C41 C3 C2 111.75(12) . . ?
N31 C3 H3 108.8 . . ?
C41 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C12 C13 C14 120.47(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C17 C16 C15 119.74(15) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 120.97(14) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C14 C15 C16 119.87(15) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C14 C13 120.13(14) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031

_shelxl_version_number           2014-1

