# Supplementary Information (SI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2400655'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2024-11-05 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N4'
_chemical_formula_weight         288.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0492(3)
_cell_length_b                   9.5052(4)
_cell_length_c                   9.9724(3)
_cell_angle_alpha                62.525(4)
_cell_angle_beta                 75.236(3)
_cell_angle_gamma                80.607(3)
_cell_volume                     734.86(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10905
_cell_measurement_theta_min      5.0510
_cell_measurement_theta_max      78.8600

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.632
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            26217
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.062
_diffrn_reflns_theta_max         79.293
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3044
_reflns_number_gt                2660
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXS-2019/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_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)+(0.0507P)²+0.2042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         3044
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.66378(11) 0.72929(12) 0.61198(11) 0.0219(2) Uani 1 1 d . . . . .
C2 C 0.54931(13) 0.80178(15) 0.67927(14) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.448816 0.764785 0.723937 0.031 Uiso 1 1 calc R U . . .
N3 N 0.59275(13) 0.92881(13) 0.67587(12) 0.0288(2) Uani 1 1 d . . . . .
C4 C 0.74395(16) 0.93864(15) 0.60098(15) 0.0299(3) Uani 1 1 d . . . . .
H4 H 0.807835 1.019248 0.580421 0.036 Uiso 1 1 calc R U . . .
C5 C 0.78970(14) 0.81737(15) 0.56030(15) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.888081 0.797933 0.507315 0.032 Uiso 1 1 calc R U . . .
C6 C 0.65565(15) 0.57923(14) 0.60791(14) 0.0263(3) Uani 1 1 d . . . . .
H6A H 0.554119 0.536582 0.666763 0.032 Uiso 1 1 calc R U . . .
H6B H 0.733859 0.502376 0.660986 0.032 Uiso 1 1 calc R U . . .
C7 C 0.67971(13) 0.59034(14) 0.44780(14) 0.0218(2) Uani 1 1 d . . . . .
C8 C 0.61474(13) 0.72010(14) 0.33104(14) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.560819 0.805323 0.350814 0.027 Uiso 1 1 calc R U . . .
C9 C 0.62963(13) 0.72271(13) 0.18982(14) 0.0226(3) Uani 1 1 d . . . . .
H9 H 0.586876 0.811010 0.111994 0.027 Uiso 1 1 calc R U . . .
C10 C 0.70765(12) 0.59622(13) 0.15724(13) 0.0207(2) Uani 1 1 d . . . . .
C11 C 0.77331(12) 0.46636(13) 0.27442(13) 0.0197(2) Uani 1 1 d . . . . .
C12 C 0.75830(13) 0.46746(13) 0.41888(13) 0.0213(2) Uani 1 1 d . . . . .
H12 H 0.803263 0.381901 0.496972 0.026 Uiso 1 1 calc R U . . .
C13 C 0.72087(14) 0.59321(14) 0.01394(14) 0.0242(3) Uani 1 1 d . . . . .
H13 H 0.678651 0.679856 -0.065614 0.029 Uiso 1 1 calc R U . . .
C14 C 0.79371(14) 0.46700(14) -0.01126(14) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.801512 0.467075 -0.108112 0.029 Uiso 1 1 calc R U . . .
C15 C 0.85761(12) 0.33627(13) 0.10537(14) 0.0214(2) Uani 1 1 d . . . . .
C16 C 0.84800(12) 0.33787(13) 0.24414(13) 0.0203(2) Uani 1 1 d . . . . .
H16 H 0.892405 0.250909 0.321654 0.024 Uiso 1 1 calc R U . . .
C17 C 0.93995(13) 0.19681(15) 0.07895(14) 0.0251(3) Uani 1 1 d . . . . .
H17A H 1.051109 0.213348 0.045518 0.030 Uiso 1 1 calc R U . . .
H17B H 0.923740 0.099349 0.177860 0.030 Uiso 1 1 calc R U . . .
N18 N 0.88910(11) 0.17322(11) -0.03647(11) 0.0215(2) Uani 1 1 d . . . . .
C19 C 0.96660(13) 0.20731(14) -0.18242(14) 0.0230(3) Uani 1 1 d . . . . .
H19 H 1.065051 0.249661 -0.223968 0.028 Uiso 1 1 calc R U . . .
N20 N 0.89043(11) 0.17526(12) -0.26028(12) 0.0243(2) Uani 1 1 d . . . . .
C21 C 0.75545(13) 0.11792(14) -0.15798(15) 0.0252(3) Uani 1 1 d . . . . .
H21 H 0.675638 0.083928 -0.180522 0.030 Uiso 1 1 calc R U . . .
C22 C 0.75217(13) 0.11665(14) -0.02013(15) 0.0246(3) Uani 1 1 d . . . . .
H22 H 0.671853 0.083511 0.068815 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3555(15) . ?
N1 C5 1.3708(15) . ?
N1 C6 1.4597(14) . ?
C2 N3 1.3129(16) . ?
C2 H2 0.9500 . ?
N3 C4 1.3766(17) . ?
C4 C5 1.3619(17) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.5108(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.3742(16) . ?
C7 C8 1.4177(17) . ?
C8 C9 1.3690(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4199(15) . ?
C9 H9 0.9500 . ?
C10 C13 1.4165(16) . ?
C10 C11 1.4233(16) . ?
C11 C16 1.4165(15) . ?
C11 C12 1.4169(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3684(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.4163(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3714(16) . ?
C15 C17 1.5104(15) . ?
C16 H16 0.9500 . ?
C17 N18 1.4590(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.3543(15) . ?
N18 C22 1.3729(15) . ?
C19 N20 1.3154(15) . ?
C19 H19 0.9500 . ?
N20 C21 1.3780(16) . ?
C21 C22 1.3620(17) . ?
C21 H21 0.9500 . ?
C22 H22 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
C2 N1 C5 106.78(10) . . ?
C2 N1 C6 125.80(10) . . ?
C5 N1 C6 127.25(10) . . ?
N3 C2 N1 112.51(11) . . ?
N3 C2 H2 123.7 . . ?
N1 C2 H2 123.7 . . ?
C2 N3 C4 104.34(10) . . ?
C5 C4 N3 110.94(11) . . ?
C5 C4 H4 124.5 . . ?
N3 C4 H4 124.5 . . ?
C4 C5 N1 105.43(11) . . ?
C4 C5 H5 127.3 . . ?
N1 C5 H5 127.3 . . ?
N1 C6 C7 114.73(10) . . ?
N1 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
N1 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C12 C7 C8 119.94(11) . . ?
C12 C7 C6 118.91(11) . . ?
C8 C7 C6 121.04(10) . . ?
C9 C8 C7 120.06(10) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.38(11) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C13 C10 C9 122.69(10) . . ?
C13 C10 C11 118.85(10) . . ?
C9 C10 C11 118.45(10) . . ?
C16 C11 C12 122.08(10) . . ?
C16 C11 C10 118.78(10) . . ?
C12 C11 C10 119.11(10) . . ?
C7 C12 C11 121.03(10) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C10 120.79(11) . . ?
C14 C13 H13 119.6 . . ?
C10 C13 H13 119.6 . . ?
C13 C14 C15 120.77(11) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.36(10) . . ?
C16 C15 C17 119.13(10) . . ?
C14 C15 C17 121.48(10) . . ?
C15 C16 C11 121.43(10) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
N18 C17 C15 113.35(9) . . ?
N18 C17 H17A 108.9 . . ?
C15 C17 H17A 108.9 . . ?
N18 C17 H17B 108.9 . . ?
C15 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 N18 C22 106.67(10) . . ?
C19 N18 C17 126.43(10) . . ?
C22 N18 C17 126.87(10) . . ?
N20 C19 N18 112.51(10) . . ?
N20 C19 H19 123.7 . . ?
N18 C19 H19 123.7 . . ?
C19 N20 C21 104.45(10) . . ?
C22 C21 N20 110.70(10) . . ?
C22 C21 H21 124.6 . . ?
N20 C21 H21 124.6 . . ?
C21 C22 N18 105.66(10) . . ?
C21 C22 H22 127.2 . . ?
N18 C22 H22 127.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.58(14) . . . . ?
C6 N1 C2 N3 174.88(11) . . . . ?
N1 C2 N3 C4 0.38(14) . . . . ?
C2 N3 C4 C5 -0.04(14) . . . . ?
N3 C4 C5 N1 -0.31(15) . . . . ?
C2 N1 C5 C4 0.52(14) . . . . ?
C6 N1 C5 C4 -174.86(11) . . . . ?
C2 N1 C6 C7 119.05(13) . . . . ?
C5 N1 C6 C7 -66.42(16) . . . . ?
N1 C6 C7 C12 143.25(11) . . . . ?
N1 C6 C7 C8 -40.64(15) . . . . ?
C12 C7 C8 C9 0.30(17) . . . . ?
C6 C7 C8 C9 -175.77(10) . . . . ?
C7 C8 C9 C10 0.89(17) . . . . ?
C8 C9 C10 C13 178.01(11) . . . . ?
C8 C9 C10 C11 -1.13(16) . . . . ?
C13 C10 C11 C16 -0.73(16) . . . . ?
C9 C10 C11 C16 178.44(9) . . . . ?
C13 C10 C11 C12 -178.97(10) . . . . ?
C9 C10 C11 C12 0.19(16) . . . . ?
C8 C7 C12 C11 -1.24(17) . . . . ?
C6 C7 C12 C11 174.92(10) . . . . ?
C16 C11 C12 C7 -177.21(10) . . . . ?
C10 C11 C12 C7 0.98(16) . . . . ?
C9 C10 C13 C14 -178.32(11) . . . . ?
C11 C10 C13 C14 0.81(17) . . . . ?
C10 C13 C14 C15 0.03(18) . . . . ?
C13 C14 C15 C16 -0.96(17) . . . . ?
C13 C14 C15 C17 -179.30(11) . . . . ?
C14 C15 C16 C11 1.05(17) . . . . ?
C17 C15 C16 C11 179.42(10) . . . . ?
C12 C11 C16 C15 177.99(10) . . . . ?
C10 C11 C16 C15 -0.20(16) . . . . ?
C16 C15 C17 N18 155.17(10) . . . . ?
C14 C15 C17 N18 -26.48(16) . . . . ?
C15 C17 N18 C19 105.74(13) . . . . ?
C15 C17 N18 C22 -72.26(15) . . . . ?
C22 N18 C19 N20 -0.69(13) . . . . ?
C17 N18 C19 N20 -179.02(10) . . . . ?
N18 C19 N20 C21 0.33(13) . . . . ?
C19 N20 C21 C22 0.15(13) . . . . ?
N20 C21 C22 N18 -0.56(13) . . . . ?
C19 N18 C22 C21 0.73(13) . . . . ?
C17 N18 C22 C21 179.06(10) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_4OK
_database_code_depnum_ccdc_archive 'CCDC 2400658'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2024-11-05 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N4 O2'
_chemical_formula_weight         324.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.149(4)
_cell_length_b                   9.6466(19)
_cell_length_c                   9.3799(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.06(3)
_cell_angle_gamma                90
_cell_volume                     1639.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    861
_cell_measurement_theta_min      2.392
_cell_measurement_theta_max      28.2095

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8358
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2892
_reflns_number_gt                2069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-2019/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_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)+(0.0513P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2892
_refine_ls_number_parameters     229
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.057
_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 0.54779(10) 0.9078(2) 0.1586(2) 0.0207(5) Uani 1 1 d . . . . .
C2 C 0.49603(14) 0.9263(3) 0.2530(3) 0.0316(7) Uani 1 1 d . . . . .
H2 H 0.502811 0.981784 0.336373 0.038 Uiso 1 1 calc R U . . .
N3 N 0.43435(12) 0.8589(3) 0.2173(2) 0.0359(6) Uani 1 1 d . . . . .
C4 C 0.44873(14) 0.7932(3) 0.0902(3) 0.0312(7) Uani 1 1 d . . . . .
H4 H 0.414950 0.735667 0.036834 0.037 Uiso 1 1 calc R U . . .
C5 C 0.51813(14) 0.8234(3) 0.0536(3) 0.0266(6) Uani 1 1 d . . . . .
H5 H 0.541518 0.792057 -0.028671 0.032 Uiso 1 1 calc R U . . .
C6 C 0.62306(12) 0.9639(3) 0.1708(3) 0.0216(6) Uani 1 1 d . . . . .
H6A H 0.621061 1.062141 0.200834 0.026 Uiso 1 1 calc R U . . .
H6B H 0.644484 0.960784 0.076011 0.026 Uiso 1 1 calc R U . . .
C7 C 0.67264(12) 0.8845(3) 0.2769(2) 0.0180(6) Uani 1 1 d . . . . .
C8 C 0.67392(12) 0.7376(3) 0.2774(2) 0.0198(6) Uani 1 1 d . . . . .
H8 H 0.641755 0.688062 0.212419 0.024 Uiso 1 1 calc R U . . .
C9 C 0.72054(13) 0.6662(3) 0.3695(2) 0.0196(6) Uani 1 1 d . . . . .
H9 H 0.720463 0.567746 0.367896 0.023 Uiso 1 1 calc R U . . .
C10 C 0.76918(12) 0.7375(3) 0.4677(2) 0.0172(5) Uani 1 1 d . . . . .
C11 C 0.76953(12) 0.8852(3) 0.4664(2) 0.0163(5) Uani 1 1 d . . . . .
C12 C 0.71965(12) 0.9556(3) 0.3708(2) 0.0180(6) Uani 1 1 d . . . . .
H12 H 0.718566 1.054030 0.371425 0.022 Uiso 1 1 calc R U . . .
C13 C 0.81752(12) 0.6672(3) 0.5679(2) 0.0190(6) Uani 1 1 d . . . . .
H13 H 0.817432 0.568741 0.570843 0.023 Uiso 1 1 calc R U . . .
C14 C 0.86404(12) 0.7394(3) 0.6600(2) 0.0188(6) Uani 1 1 d . . . . .
H14 H 0.896066 0.690870 0.726063 0.023 Uiso 1 1 calc R U . . .
C15 C 0.86481(12) 0.8867(3) 0.6576(2) 0.0168(5) Uani 1 1 d . . . . .
C16 C 0.81889(12) 0.9570(3) 0.5622(2) 0.0166(6) Uani 1 1 d . . . . .
H16 H 0.820196 1.055394 0.560199 0.020 Uiso 1 1 calc R U . . .
C17 C 0.91220(12) 0.9664(3) 0.7669(3) 0.0206(6) Uani 1 1 d . . . . .
H17A H 0.914618 1.064483 0.736407 0.025 Uiso 1 1 calc R U . . .
H17B H 0.888319 0.964048 0.859351 0.025 Uiso 1 1 calc R U . . .
N18 N 0.98735(10) 0.9127(2) 0.78803(19) 0.0162(5) Uani 1 1 d . . . . .
C19 C 1.01708(13) 0.8507(3) 0.9070(2) 0.0201(6) Uani 1 1 d . . . . .
H19 H 0.990918 0.834190 0.990379 0.024 Uiso 1 1 calc R U . . .
N20 N 1.08657(11) 0.8159(2) 0.8936(2) 0.0216(5) Uani 1 1 d . . . . .
C21 C 1.10195(13) 0.8588(3) 0.7585(2) 0.0213(6) Uani 1 1 d . . . . .
H21 H 1.148345 0.848499 0.717348 0.026 Uiso 1 1 calc R U . . .
C22 C 1.04183(13) 0.9177(3) 0.6926(2) 0.0213(6) Uani 1 1 d . . . . .
H22 H 1.038080 0.955179 0.598826 0.026 Uiso 1 1 calc R U . . .
O23 O 0.29585(9) 0.7949(2) 0.31512(18) 0.0265(5) Uani 1 1 d D . . . .
H24A H 0.2531(12) 0.784(3) -0.033(2) 0.032 Uiso 1 1 d D U . . .
H23A H 0.3446(10) 0.823(3) 0.296(3) 0.032 Uiso 1 1 d D U . . .
H23B H 0.2668(12) 0.809(3) 0.227(2) 0.032 Uiso 1 1 d D U . . .
H24B H 0.1775(10) 0.816(3) 0.010(3) 0.032 Uiso 1 1 d D U . . .
O24 O 0.22757(10) 0.81635(19) 0.04411(18) 0.0238(4) Uani 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
N1 C2 1.337(3) . ?
N1 C5 1.366(3) . ?
N1 C6 1.468(3) . ?
C2 N3 1.322(3) . ?
C2 H2 0.9500 . ?
N3 C4 1.387(4) . ?
C4 C5 1.355(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.513(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.376(3) . ?
C7 C8 1.418(3) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(3) . ?
C9 H9 0.9500 . ?
C10 C13 1.423(3) . ?
C10 C11 1.425(3) . ?
C11 C12 1.414(3) . ?
C11 C16 1.415(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.421(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.370(3) . ?
C15 C17 1.512(3) . ?
C16 H16 0.9500 . ?
C17 N18 1.462(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.353(3) . ?
N18 C22 1.370(3) . ?
C19 N20 1.318(3) . ?
C19 H19 0.9500 . ?
N20 C21 1.376(3) . ?
C21 C22 1.350(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O23 H23A 0.952(17) . ?
O23 H23B 0.963(16) . ?
O24 H24A 0.937(17) . ?
O24 H24B 0.948(16) . ?

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
C2 N1 C5 107.1(2) . . ?
C2 N1 C6 125.6(2) . . ?
C5 N1 C6 127.2(2) . . ?
N3 C2 N1 112.4(3) . . ?
N3 C2 H2 123.8 . . ?
N1 C2 H2 123.8 . . ?
C2 N3 C4 104.3(2) . . ?
C5 C4 N3 109.9(2) . . ?
C5 C4 H4 125.1 . . ?
N3 C4 H4 125.1 . . ?
C4 C5 N1 106.3(2) . . ?
C4 C5 H5 126.8 . . ?
N1 C5 H5 126.8 . . ?
N1 C6 C7 112.5(2) . . ?
N1 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C12 C7 C8 119.1(2) . . ?
C12 C7 C6 119.7(2) . . ?
C8 C7 C6 121.1(2) . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C13 122.6(2) . . ?
C9 C10 C11 118.8(2) . . ?
C13 C10 C11 118.6(2) . . ?
C12 C11 C16 122.0(2) . . ?
C12 C11 C10 118.9(2) . . ?
C16 C11 C10 119.1(2) . . ?
C7 C12 C11 121.4(2) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C10 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C10 C13 H13 119.6 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 C17 119.7(2) . . ?
C14 C15 C17 120.2(2) . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N18 C17 C15 113.8(2) . . ?
N18 C17 H17A 108.8 . . ?
C15 C17 H17A 108.8 . . ?
N18 C17 H17B 108.8 . . ?
C15 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 N18 C22 106.5(2) . . ?
C19 N18 C17 126.6(2) . . ?
C22 N18 C17 126.9(2) . . ?
N20 C19 N18 112.1(2) . . ?
N20 C19 H19 124.0 . . ?
N18 C19 H19 124.0 . . ?
C19 N20 C21 104.7(2) . . ?
C22 C21 N20 110.5(2) . . ?
C22 C21 H21 124.8 . . ?
N20 C21 H21 124.8 . . ?
C21 C22 N18 106.3(2) . . ?
C21 C22 H22 126.9 . . ?
N18 C22 H22 126.9 . . ?
H23A O23 H23B 106(2) . . ?
H24A O24 H24B 104(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 0.4(3) . . . . ?
C6 N1 C2 N3 -177.3(2) . . . . ?
N1 C2 N3 C4 -0.1(3) . . . . ?
C2 N3 C4 C5 -0.2(3) . . . . ?
N3 C4 C5 N1 0.4(3) . . . . ?
C2 N1 C5 C4 -0.5(3) . . . . ?
C6 N1 C5 C4 177.2(2) . . . . ?
C2 N1 C6 C7 76.4(3) . . . . ?
C5 N1 C6 C7 -100.8(3) . . . . ?
N1 C6 C7 C12 -136.9(2) . . . . ?
N1 C6 C7 C8 45.8(3) . . . . ?
C12 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C9 177.6(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C13 178.5(2) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C9 C10 C11 C12 2.2(3) . . . . ?
C13 C10 C11 C12 -177.62(19) . . . . ?
C9 C10 C11 C16 -178.79(19) . . . . ?
C13 C10 C11 C16 1.4(3) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C6 C7 C12 C11 -176.7(2) . . . . ?
C16 C11 C12 C7 179.1(2) . . . . ?
C10 C11 C12 C7 -1.9(3) . . . . ?
C9 C10 C13 C14 179.4(2) . . . . ?
C11 C10 C13 C14 -0.8(3) . . . . ?
C10 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C13 C14 C15 C17 175.4(2) . . . . ?
C14 C15 C16 C11 0.9(3) . . . . ?
C17 C15 C16 C11 -174.8(2) . . . . ?
C12 C11 C16 C15 177.5(2) . . . . ?
C10 C11 C16 C15 -1.5(3) . . . . ?
C16 C15 C17 N18 -138.4(2) . . . . ?
C14 C15 C17 N18 45.9(3) . . . . ?
C15 C17 N18 C19 -112.5(3) . . . . ?
C15 C17 N18 C22 68.9(3) . . . . ?
C22 N18 C19 N20 -0.1(3) . . . . ?
C17 N18 C19 N20 -178.9(2) . . . . ?
N18 C19 N20 C21 0.3(3) . . . . ?
C19 N20 C21 C22 -0.4(3) . . . . ?
N20 C21 C22 N18 0.3(3) . . . . ?
C19 N18 C22 C21 -0.1(3) . . . . ?
C17 N18 C22 C21 178.7(2) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_2cor
_database_code_depnum_ccdc_archive 'CCDC 2400656'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2024-11-05 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N4 O0.50'
_chemical_formula_weight         297.35

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.5410(4)
_cell_length_b                   5.46830(10)
_cell_length_c                   26.6872(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.478(2)
_cell_angle_gamma                90
_cell_volume                     2926.82(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6160
_cell_measurement_theta_min      3.3810
_cell_measurement_theta_max      77.1580

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.676
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            10042
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.392
_diffrn_reflns_theta_max         79.310
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2997
_reflns_number_gt                2631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXS-2019/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_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)+(0.0457P)²+1.8118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.23134(5) -0.03557(18) 0.31906(4) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.17460(6) -0.1648(2) 0.31579(5) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.172589 -0.319430 0.331613 0.030 Uiso 1 1 calc R U . . .
N3 N 0.12225(5) -0.0518(2) 0.28810(4) 0.0293(3) Uani 1 1 d . . . . .
C4 C 0.14714(6) 0.1626(3) 0.27276(5) 0.0272(3) Uani 1 1 d . . . . .
H4 H 0.121247 0.284466 0.252189 0.033 Uiso 1 1 calc R U . . .
C5 C 0.21438(6) 0.1748(2) 0.29135(5) 0.0253(3) Uani 1 1 d . . . . .
H5 H 0.243476 0.302825 0.286167 0.030 Uiso 1 1 calc R U . . .
C6 C 0.29867(6) -0.1158(2) 0.34510(5) 0.0232(3) Uani 1 1 d . . . . .
H6A H 0.322441 -0.179310 0.319264 0.028 Uiso 1 1 calc R U . . .
H6B H 0.294907 -0.250539 0.369078 0.028 Uiso 1 1 calc R U . . .
C7 C 0.33843(5) 0.0900(2) 0.37439(4) 0.0207(2) Uani 1 1 d . . . . .
C8 C 0.33134(6) 0.1428(2) 0.42493(5) 0.0223(3) Uani 1 1 d . . . . .
H8 H 0.301763 0.048040 0.439915 0.027 Uiso 1 1 calc R U . . .
C9 C 0.36681(6) 0.3293(2) 0.45232(4) 0.0217(3) Uani 1 1 d . . . . .
H9 H 0.361745 0.362333 0.486215 0.026 Uiso 1 1 calc R U . . .
C10 C 0.41106(5) 0.4739(2) 0.43060(4) 0.0195(2) Uani 1 1 d . . . . .
C11 C 0.41845(5) 0.4218(2) 0.37980(4) 0.0193(2) Uani 1 1 d . . . . .
C12 C 0.38139(6) 0.2258(2) 0.35267(4) 0.0211(3) Uani 1 1 d . . . . .
H12 H 0.386364 0.187955 0.318962 0.025 Uiso 1 1 calc R U . . .
C13 C 0.44832(6) 0.6686(2) 0.45772(4) 0.0217(2) Uani 1 1 d . . . . .
H13 H 0.443332 0.706681 0.491421 0.026 Uiso 1 1 calc R U . . .
C14 C 0.49138(6) 0.8029(2) 0.43619(5) 0.0218(3) Uani 1 1 d . . . . .
H14 H 0.516297 0.931479 0.455258 0.026 Uiso 1 1 calc R U . . .
C15 C 0.49920(6) 0.7523(2) 0.38577(4) 0.0200(2) Uani 1 1 d . . . . .
C16 C 0.46323(6) 0.5658(2) 0.35845(4) 0.0198(2) Uani 1 1 d . . . . .
H16 H 0.468398 0.532350 0.324589 0.024 Uiso 1 1 calc R U . . .
C17 C 0.54520(6) 0.9050(2) 0.36099(5) 0.0238(3) Uani 1 1 d . . . . .
H17A H 0.561056 0.803210 0.335359 0.029 Uiso 1 1 calc R U . . .
H17B H 0.519426 1.042829 0.342456 0.029 Uiso 1 1 calc R U . . .
N18 N 0.60296(5) 1.00302(18) 0.39712(4) 0.0208(2) Uani 1 1 d . . . . .
C19 C 0.60917(6) 1.2330(2) 0.41635(5) 0.0242(3) Uani 1 1 d . . . . .
H19 H 0.575255 1.353679 0.408163 0.029 Uiso 1 1 calc R U . . .
N20 N 0.66723(5) 1.2715(2) 0.44761(4) 0.0253(2) Uani 1 1 d . . . . .
C21 C 0.70030(6) 1.0520(2) 0.44861(5) 0.0236(3) Uani 1 1 d . . . . .
H21 H 0.744034 1.021513 0.468050 0.028 Uiso 1 1 calc R U . . .
C22 C 0.66177(6) 0.8841(2) 0.41790(5) 0.0232(3) Uani 1 1 d . . . . .
H22 H 0.673085 0.719663 0.412055 0.028 Uiso 1 1 calc R U . . .
O23 O 0.000000 -0.3203(3) 0.250000 0.0322(3) Uani 1 2 d S T P . .
H23 H 0.0350(8) -0.222(3) 0.2626(7) 0.039 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3495(15) . ?
N1 C5 1.3711(16) . ?
N1 C6 1.4740(14) . ?
C2 N3 1.3195(17) . ?
C2 H2 0.9500 . ?
N3 C4 1.3760(18) . ?
C4 C5 1.3645(18) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.5060(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.3738(17) . ?
C7 C8 1.4171(17) . ?
C8 C9 1.3696(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4194(17) . ?
C9 H9 0.9500 . ?
C10 C13 1.4157(17) . ?
C10 C11 1.4251(16) . ?
C11 C12 1.4192(17) . ?
C11 C16 1.4201(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3679(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.4167(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3730(17) . ?
C15 C17 1.5155(16) . ?
C16 H16 0.9500 . ?
C17 N18 1.4596(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.3540(16) . ?
N18 C22 1.3784(15) . ?
C19 N20 1.3163(16) . ?
C19 H19 0.9500 . ?
N20 C21 1.3767(16) . ?
C21 C22 1.3639(18) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O23 H23 0.903(17) . ?
O23 H23 0.903(17) 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
C2 N1 C5 106.81(10) . . ?
C2 N1 C6 125.73(11) . . ?
C5 N1 C6 127.37(10) . . ?
N3 C2 N1 112.26(11) . . ?
N3 C2 H2 123.9 . . ?
N1 C2 H2 123.9 . . ?
C2 N3 C4 104.79(10) . . ?
C5 C4 N3 110.21(11) . . ?
C5 C4 H4 124.9 . . ?
N3 C4 H4 124.9 . . ?
C4 C5 N1 105.92(11) . . ?
C4 C5 H5 127.0 . . ?
N1 C5 H5 127.0 . . ?
N1 C6 C7 111.77(10) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C12 C7 C8 119.92(11) . . ?
C12 C7 C6 120.71(11) . . ?
C8 C7 C6 119.37(11) . . ?
C9 C8 C7 120.49(11) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.71(11) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C13 C10 C9 122.23(10) . . ?
C13 C10 C11 118.67(11) . . ?
C9 C10 C11 119.11(11) . . ?
C12 C11 C16 122.45(10) . . ?
C12 C11 C10 118.71(11) . . ?
C16 C11 C10 118.84(11) . . ?
C7 C12 C11 121.06(11) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C10 121.08(11) . . ?
C14 C13 H13 119.5 . . ?
C10 C13 H13 119.5 . . ?
C13 C14 C15 120.69(11) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.42(11) . . ?
C16 C15 C17 119.49(10) . . ?
C14 C15 C17 121.07(11) . . ?
C15 C16 C11 121.30(11) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
N18 C17 C15 114.12(10) . . ?
N18 C17 H17A 108.7 . . ?
C15 C17 H17A 108.7 . . ?
N18 C17 H17B 108.7 . . ?
C15 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 N18 C22 106.45(10) . . ?
C19 N18 C17 126.02(10) . . ?
C22 N18 C17 127.52(11) . . ?
N20 C19 N18 112.75(11) . . ?
N20 C19 H19 123.6 . . ?
N18 C19 H19 123.6 . . ?
C19 N20 C21 104.40(10) . . ?
C22 C21 N20 110.81(11) . . ?
C22 C21 H21 124.6 . . ?
N20 C21 H21 124.6 . . ?
C21 C22 N18 105.58(11) . . ?
C21 C22 H22 127.2 . . ?
N18 C22 H22 127.2 . . ?
H23 O23 H23 107(2) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.28(14) . . . . ?
C6 N1 C2 N3 -177.03(11) . . . . ?
N1 C2 N3 C4 0.03(14) . . . . ?
C2 N3 C4 C5 0.25(15) . . . . ?
N3 C4 C5 N1 -0.42(14) . . . . ?
C2 N1 C5 C4 0.42(13) . . . . ?
C6 N1 C5 C4 177.09(11) . . . . ?
C2 N1 C6 C7 -139.36(12) . . . . ?
C5 N1 C6 C7 44.56(16) . . . . ?
N1 C6 C7 C12 -95.29(13) . . . . ?
N1 C6 C7 C8 84.84(13) . . . . ?
C12 C7 C8 C9 0.30(17) . . . . ?
C6 C7 C8 C9 -179.82(11) . . . . ?
C7 C8 C9 C10 0.28(18) . . . . ?
C8 C9 C10 C13 179.77(11) . . . . ?
C8 C9 C10 C11 -0.28(17) . . . . ?
C13 C10 C11 C12 179.68(10) . . . . ?
C9 C10 C11 C12 -0.28(16) . . . . ?
C13 C10 C11 C16 0.48(16) . . . . ?
C9 C10 C11 C16 -179.47(10) . . . . ?
C8 C7 C12 C11 -0.88(17) . . . . ?
C6 C7 C12 C11 179.25(10) . . . . ?
C16 C11 C12 C7 -179.98(11) . . . . ?
C10 C11 C12 C7 0.86(17) . . . . ?
C9 C10 C13 C14 179.03(11) . . . . ?
C11 C10 C13 C14 -0.92(17) . . . . ?
C10 C13 C14 C15 0.80(18) . . . . ?
C13 C14 C15 C16 -0.22(17) . . . . ?
C13 C14 C15 C17 178.12(11) . . . . ?
C14 C15 C16 C11 -0.22(17) . . . . ?
C17 C15 C16 C11 -178.58(10) . . . . ?
C12 C11 C16 C15 -179.09(11) . . . . ?
C10 C11 C16 C15 0.07(17) . . . . ?
C16 C15 C17 N18 -150.27(11) . . . . ?
C14 C15 C17 N18 31.40(16) . . . . ?
C15 C17 N18 C19 -99.55(14) . . . . ?
C15 C17 N18 C22 81.29(14) . . . . ?
C22 N18 C19 N20 0.23(14) . . . . ?
C17 N18 C19 N20 -179.08(11) . . . . ?
N18 C19 N20 C21 -0.18(14) . . . . ?
C19 N20 C21 C22 0.06(14) . . . . ?
N20 C21 C22 N18 0.08(14) . . . . ?
C19 N18 C22 C21 -0.18(13) . . . . ?
C17 N18 C22 C21 179.11(11) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2400657'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2024-11-05 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N4 O'
_chemical_formula_weight         306.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-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                   9.72620(10)
_cell_length_b                   10.12810(10)
_cell_length_c                   31.3817(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3091.35(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13862
_cell_measurement_theta_min      5.3250
_cell_measurement_theta_max      76.5240

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.680
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            26217
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         77.359
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3187
_reflns_number_gt                2827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXS-2019/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  direct
_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)+(0.0592P)²+0.8505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3187
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
N1 N 0.58473(9) 0.78184(9) 0.50474(3) 0.0192(2) Uani 1 1 d . . . . .
C2 C 0.64445(12) 0.88959(11) 0.48717(4) 0.0213(3) Uani 1 1 d . . . . .
H2 H 0.655690 0.971357 0.501595 0.026 Uiso 1 1 calc R U . . .
N3 N 0.68518(10) 0.86788(10) 0.44776(3) 0.0243(2) Uani 1 1 d . . . . .
C4 C 0.64968(12) 0.73834(12) 0.43960(4) 0.0243(3) Uani 1 1 d . . . . .
H4 H 0.665722 0.693508 0.413474 0.029 Uiso 1 1 calc R U . . .
C5 C 0.58858(13) 0.68448(12) 0.47431(4) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.555074 0.596785 0.477051 0.030 Uiso 1 1 calc R U . . .
C6 C 0.53219(11) 0.76858(11) 0.54811(4) 0.0216(3) Uani 1 1 d . . . . .
H6A H 0.434399 0.741703 0.546993 0.026 Uiso 1 1 calc R U . . .
H6B H 0.537167 0.855328 0.562568 0.026 Uiso 1 1 calc R U . . .
C7 C 0.61228(11) 0.66811(11) 0.57370(4) 0.0188(2) Uani 1 1 d . . . . .
C8 C 0.75853(11) 0.66876(11) 0.57264(3) 0.0197(2) Uani 1 1 d . . . . .
H8 H 0.805287 0.729927 0.554848 0.024 Uiso 1 1 calc R U . . .
C9 C 0.83253(11) 0.58206(11) 0.59703(4) 0.0198(2) Uani 1 1 d . . . . .
H9 H 0.930128 0.583820 0.596005 0.024 Uiso 1 1 calc R U . . .
C10 C 0.76499(11) 0.48948(11) 0.62386(3) 0.0176(2) Uani 1 1 d . . . . .
C11 C 0.61877(11) 0.48934(11) 0.62538(3) 0.0177(2) Uani 1 1 d . . . . .
C12 C 0.54503(11) 0.58010(11) 0.59947(3) 0.0189(2) Uani 1 1 d . . . . .
H12 H 0.447371 0.579730 0.600045 0.023 Uiso 1 1 calc R U . . .
C13 C 0.83893(11) 0.39708(11) 0.64917(4) 0.0193(2) Uani 1 1 d . . . . .
H13 H 0.936564 0.396340 0.648382 0.023 Uiso 1 1 calc R U . . .
C14 C 0.77035(11) 0.30904(11) 0.67469(3) 0.0195(2) Uani 1 1 d . . . . .
H14 H 0.820882 0.247484 0.691313 0.023 Uiso 1 1 calc R U . . .
C15 C 0.62438(11) 0.30913(11) 0.67646(4) 0.0187(2) Uani 1 1 d . . . . .
C16 C 0.55137(11) 0.39827(11) 0.65262(3) 0.0189(2) Uani 1 1 d . . . . .
H16 H 0.453866 0.399054 0.654372 0.023 Uiso 1 1 calc R U . . .
C17 C 0.54957(12) 0.20662(11) 0.70264(4) 0.0222(3) Uani 1 1 d . . . . .
H17A H 0.452003 0.233058 0.705476 0.027 Uiso 1 1 calc R U . . .
H17B H 0.552208 0.121165 0.687340 0.027 Uiso 1 1 calc R U . . .
N18 N 0.60810(9) 0.18887(9) 0.74511(3) 0.0193(2) Uani 1 1 d . . . . .
C19 C 0.66922(12) 0.07912(11) 0.76074(4) 0.0215(3) Uani 1 1 d . . . . .
H19 H 0.681913 0.000209 0.744860 0.026 Uiso 1 1 calc R U . . .
N20 N 0.70908(10) 0.09438(10) 0.80056(3) 0.0234(2) Uani 1 1 d . . . . .
C21 C 0.67150(12) 0.22165(12) 0.81099(4) 0.0236(3) Uani 1 1 d . . . . .
H21 H 0.686465 0.261966 0.837931 0.028 Uiso 1 1 calc R U . . .
C22 C 0.61005(12) 0.28094(11) 0.77721(4) 0.0229(3) Uani 1 1 d . . . . .
H22 H 0.575364 0.368545 0.776020 0.027 Uiso 1 1 calc R U . . .
O23 O 0.67587(9) 1.03617(9) 0.37358(3) 0.0259(2) Uani 1 1 d . . . . .
H23A H 0.710(2) 0.994(2) 0.3514(6) 0.051(5) Uiso 1 1 d . . . . .
H23B H 0.6897(18) 0.9843(19) 0.3958(6) 0.048(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
N1 C2 1.3536(14) . ?
N1 C5 1.3731(15) . ?
N1 C6 1.4599(14) . ?
C2 N3 1.3174(16) . ?
C2 H2 0.9500 . ?
N3 C4 1.3806(16) . ?
C4 C5 1.3557(17) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.5123(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.3699(15) . ?
C7 C8 1.4229(15) . ?
C8 C9 1.3691(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4211(15) . ?
C9 H9 0.9500 . ?
C10 C13 1.4225(15) . ?
C10 C11 1.4230(15) . ?
C11 C16 1.4181(15) . ?
C11 C12 1.4214(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3716(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.4208(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3709(16) . ?
C15 C17 1.5107(15) . ?
C16 H16 0.9500 . ?
C17 N18 1.4605(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.3527(15) . ?
N18 C22 1.3730(14) . ?
C19 N20 1.3173(16) . ?
C19 H19 0.9500 . ?
N20 C21 1.3793(15) . ?
C21 C22 1.3570(17) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O23 H23A 0.88(2) . ?
O23 H23B 0.88(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
C2 N1 C5 106.51(9) . . ?
C2 N1 C6 127.15(10) . . ?
C5 N1 C6 126.28(10) . . ?
N3 C2 N1 112.14(10) . . ?
N3 C2 H2 123.9 . . ?
N1 C2 H2 123.9 . . ?
C2 N3 C4 104.93(10) . . ?
C5 C4 N3 110.06(11) . . ?
C5 C4 H4 125.0 . . ?
N3 C4 H4 125.0 . . ?
C4 C5 N1 106.37(10) . . ?
C4 C5 H5 126.8 . . ?
N1 C5 H5 126.8 . . ?
N1 C6 C7 112.12(9) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C12 C7 C8 119.61(10) . . ?
C12 C7 C6 120.36(10) . . ?
C8 C7 C6 119.97(10) . . ?
C9 C8 C7 120.63(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.75(10) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C13 122.09(10) . . ?
C9 C10 C11 118.85(10) . . ?
C13 C10 C11 119.07(10) . . ?
C16 C11 C12 122.15(10) . . ?
C16 C11 C10 118.87(10) . . ?
C12 C11 C10 118.98(10) . . ?
C7 C12 C11 121.17(10) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C10 120.52(10) . . ?
C14 C13 H13 119.7 . . ?
C10 C13 H13 119.7 . . ?
C13 C14 C15 120.56(10) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.77(10) . . ?
C16 C15 C17 119.99(10) . . ?
C14 C15 C17 120.15(10) . . ?
C15 C16 C11 121.19(10) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N18 C17 C15 113.14(9) . . ?
N18 C17 H17A 109.0 . . ?
C15 C17 H17A 109.0 . . ?
N18 C17 H17B 109.0 . . ?
C15 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 N18 C22 106.61(10) . . ?
C19 N18 C17 127.12(10) . . ?
C22 N18 C17 126.27(10) . . ?
N20 C19 N18 112.15(10) . . ?
N20 C19 H19 123.9 . . ?
N18 C19 H19 123.9 . . ?
C19 N20 C21 104.88(10) . . ?
C22 C21 N20 110.17(11) . . ?
C22 C21 H21 124.9 . . ?
N20 C21 H21 124.9 . . ?
C21 C22 N18 106.19(10) . . ?
C21 C22 H22 126.9 . . ?
N18 C22 H22 126.9 . . ?
H23A O23 H23B 106.3(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 0.36(13) . . . . ?
C6 N1 C2 N3 177.69(10) . . . . ?
N1 C2 N3 C4 -0.13(13) . . . . ?
C2 N3 C4 C5 -0.16(13) . . . . ?
N3 C4 C5 N1 0.37(13) . . . . ?
C2 N1 C5 C4 -0.44(13) . . . . ?
C6 N1 C5 C4 -177.79(10) . . . . ?
C2 N1 C6 C7 -114.85(12) . . . . ?
C5 N1 C6 C7 61.97(14) . . . . ?
N1 C6 C7 C12 -137.26(10) . . . . ?
N1 C6 C7 C8 45.74(14) . . . . ?
C12 C7 C8 C9 0.20(16) . . . . ?
C6 C7 C8 C9 177.22(10) . . . . ?
C7 C8 C9 C10 0.09(16) . . . . ?
C8 C9 C10 C13 179.20(10) . . . . ?
C8 C9 C10 C11 -0.75(16) . . . . ?
C9 C10 C11 C16 -179.09(10) . . . . ?
C13 C10 C11 C16 0.96(15) . . . . ?
C9 C10 C11 C12 1.11(15) . . . . ?
C13 C10 C11 C12 -178.84(10) . . . . ?
C8 C7 C12 C11 0.19(16) . . . . ?
C6 C7 C12 C11 -176.82(10) . . . . ?
C16 C11 C12 C7 179.36(10) . . . . ?
C10 C11 C12 C7 -0.85(16) . . . . ?
C9 C10 C13 C14 -179.96(10) . . . . ?
C11 C10 C13 C14 0.00(15) . . . . ?
C10 C13 C14 C15 -0.36(16) . . . . ?
C13 C14 C15 C16 -0.27(16) . . . . ?
C13 C14 C15 C17 176.38(10) . . . . ?
C14 C15 C16 C11 1.26(16) . . . . ?
C17 C15 C16 C11 -175.39(10) . . . . ?
C12 C11 C16 C15 178.19(10) . . . . ?
C10 C11 C16 C15 -1.60(16) . . . . ?
C16 C15 C17 N18 -137.24(11) . . . . ?
C14 C15 C17 N18 46.12(14) . . . . ?
C15 C17 N18 C19 -115.29(12) . . . . ?
C15 C17 N18 C22 65.54(14) . . . . ?
C22 N18 C19 N20 0.43(13) . . . . ?
C17 N18 C19 N20 -178.88(10) . . . . ?
N18 C19 N20 C21 -0.14(13) . . . . ?
C19 N20 C21 C22 -0.20(13) . . . . ?
N20 C21 C22 N18 0.46(13) . . . . ?
C19 N18 C22 C21 -0.53(12) . . . . ?
C17 N18 C22 C21 178.79(10) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046



