# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1THF
_database_code_depnum_ccdc_archive 'CCDC 2253373'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University 
Poland
;
_audit_update_record             
;
2023-04-02 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2'
_chemical_formula_weight         336.42

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      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                   20.7777(2)
_cell_length_b                   10.58810(10)
_cell_length_c                   8.25020(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.6050(10)
_cell_angle_gamma                90
_cell_volume                     1809.16(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20029
_cell_measurement_theta_min      2.1370
_cell_measurement_theta_max      76.4520

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.556
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80997
_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            39998
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         77.222
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3774
_reflns_number_gt                3273
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0456P)²+0.5778P] 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         3774
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0936
_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
N1 N 1.01231(10) 0.72862(18) 1.39012(19) 0.0763(6) Uani 1 1 d . . . . .
C2 C 0.95380(13) 0.75439(19) 1.4321(2) 0.0758(6) Uani 1 1 d . . . . .
H2 H 0.947227 0.833639 1.482220 0.091 Uiso 1 1 calc R U . . .
C3 C 0.90182(8) 0.67490(15) 1.40864(18) 0.0508(4) Uani 1 1 d . . . . .
H3 H 0.860884 0.699229 1.441898 0.061 Uiso 1 1 calc R U . . .
C4 C 0.90966(6) 0.55934(12) 1.33623(13) 0.0281(3) Uani 1 1 d . . . . .
C5 C 0.97033(6) 0.52950(14) 1.29199(16) 0.0388(3) Uani 1 1 d . . . . .
H5 H 0.978159 0.450663 1.242236 0.047 Uiso 1 1 calc R U . . .
C6 C 1.01962(7) 0.6162(2) 1.32116(19) 0.0612(5) Uani 1 1 d . . . . .
H6 H 1.061257 0.594296 1.290214 0.073 Uiso 1 1 calc R U . . .
C7 C 0.85459(6) 0.46814(13) 1.30600(15) 0.0355(3) Uani 1 1 d . . . . .
H7A H 0.821026 0.487767 1.380851 0.043 Uiso 1 1 calc R U . . .
H7B H 0.870374 0.381444 1.330428 0.043 Uiso 1 1 calc R U . . .
C8 C 0.82460(5) 0.47283(11) 1.13190(14) 0.0284(3) Uani 1 1 d . . . . .
C9 C 0.77721(6) 0.56146(12) 1.08631(14) 0.0296(3) Uani 1 1 d . . . . .
H9 H 0.765049 0.621499 1.163795 0.036 Uiso 1 1 calc R U . . .
C10 C 0.74730(5) 0.56391(12) 0.92962(14) 0.0274(2) Uani 1 1 d . . . . .
H10 H 0.715020 0.625383 0.901430 0.033 Uiso 1 1 calc R U . . .
C11 C 0.76417(5) 0.47706(11) 0.81328(13) 0.0230(2) Uani 1 1 d . . . . .
C12 C 0.81346(5) 0.39115(11) 0.85774(14) 0.0281(2) Uani 1 1 d . . . . .
H12 H 0.826848 0.333016 0.779428 0.034 Uiso 1 1 calc R U . . .
C13 C 0.84323(6) 0.38935(12) 1.01464(15) 0.0309(3) Uani 1 1 d . . . . .
H13 H 0.876746 0.330243 1.042034 0.037 Uiso 1 1 calc R U . . .
C14 C 0.72930(5) 0.47289(10) 0.64874(13) 0.0224(2) Uani 1 1 d . . . . .
C15 C 0.70589(5) 0.58248(11) 0.57033(13) 0.0250(2) Uani 1 1 d . . . . .
H15 H 0.712842 0.661955 0.622248 0.030 Uiso 1 1 calc R U . . .
C16 C 0.67255(5) 0.57706(11) 0.41745(13) 0.0259(2) Uani 1 1 d . . . . .
H16 H 0.657477 0.652912 0.365907 0.031 Uiso 1 1 calc R U . . .
C17 C 0.66096(5) 0.46204(11) 0.33898(13) 0.0250(2) Uani 1 1 d . . . . .
C18 C 0.68414(5) 0.35251(11) 0.41671(13) 0.0253(2) Uani 1 1 d . . . . .
H18 H 0.676654 0.273036 0.365153 0.030 Uiso 1 1 calc R U . . .
C19 C 0.71804(5) 0.35789(11) 0.56857(13) 0.0245(2) Uani 1 1 d . . . . .
H19 H 0.733845 0.282048 0.618793 0.029 Uiso 1 1 calc R U . . .
C20 C 0.62500(5) 0.45488(12) 0.17201(13) 0.0292(3) Uani 1 1 d . . . . .
H20A H 0.627819 0.538047 0.118197 0.035 Uiso 1 1 calc R U . . .
H20B H 0.646735 0.392272 0.105936 0.035 Uiso 1 1 calc R U . . .
C21 C 0.55459(5) 0.41886(11) 0.17369(12) 0.0238(2) Uani 1 1 d . . . . .
C22 C 0.51356(5) 0.47980(11) 0.27337(13) 0.0271(2) Uani 1 1 d . . . . .
H22 H 0.530045 0.542709 0.347622 0.033 Uiso 1 1 calc R U . . .
C23 C 0.44860(6) 0.44872(11) 0.26434(14) 0.0273(2) Uani 1 1 d . . . . .
H23 H 0.421579 0.492792 0.332755 0.033 Uiso 1 1 calc R U . . .
N24 N 0.42175(5) 0.36029(9) 0.16491(11) 0.0281(2) Uani 1 1 d . . . . .
C25 C 0.46157(6) 0.30231(11) 0.06977(14) 0.0301(3) Uani 1 1 d . . . . .
H25 H 0.443795 0.239630 -0.003074 0.036 Uiso 1 1 calc R U . . .
C26 C 0.52712(6) 0.32726(11) 0.06991(14) 0.0284(2) Uani 1 1 d . . . . .
H26 H 0.552900 0.282035 -0.000385 0.034 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 1.319(3) . ?
N1 C6 1.334(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.3770(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3769(18) . ?
C4 C7 1.5027(16) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5199(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.3882(18) . ?
C8 C9 1.3900(17) . ?
C9 C10 1.3889(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3942(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3966(16) . ?
C11 C14 1.4872(14) . ?
C12 C13 1.3893(16) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.3965(16) . ?
C14 C15 1.3968(15) . ?
C15 C16 1.3906(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3911(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3923(16) . ?
C17 C20 1.5155(15) . ?
C18 C19 1.3883(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.5130(15) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.3861(16) . ?
C21 C22 1.3900(16) . ?
C22 C23 1.3854(16) . ?
C22 H22 0.9500 . ?
C23 N24 1.3370(15) . ?
C23 H23 0.9500 . ?
N24 C25 1.3349(16) . ?
C25 C26 1.3871(17) . ?
C25 H25 0.9500 . ?
C26 H26 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 C6 115.83(14) . . ?
N1 C2 C3 124.62(18) . . ?
N1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 119.18(17) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 117.49(13) . . ?
C5 C4 C7 120.64(12) . . ?
C3 C4 C7 121.87(13) . . ?
C4 C5 C6 118.88(15) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 123.98(17) . . ?
N1 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
C4 C7 C8 112.63(10) . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 118.19(10) . . ?
C13 C8 C7 121.44(11) . . ?
C9 C8 C7 120.37(11) . . ?
C10 C9 C8 121.25(11) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.66(11) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 117.93(10) . . ?
C10 C11 C14 121.13(10) . . ?
C12 C11 C14 120.90(10) . . ?
C13 C12 C11 121.05(11) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C8 C13 C12 120.83(11) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C19 C14 C15 117.78(10) . . ?
C19 C14 C11 120.60(10) . . ?
C15 C14 C11 121.61(10) . . ?
C16 C15 C14 121.03(11) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.88(10) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 118.32(10) . . ?
C16 C17 C20 121.40(10) . . ?
C18 C17 C20 120.27(11) . . ?
C19 C18 C17 120.87(11) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 121.12(10) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
C21 C20 C17 114.26(9) . . ?
C21 C20 H20A 108.7 . . ?
C17 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C17 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C26 C21 C22 116.65(10) . . ?
C26 C21 C20 121.42(10) . . ?
C22 C21 C20 121.86(10) . . ?
C23 C22 C21 119.93(10) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
N24 C23 C22 123.79(11) . . ?
N24 C23 H23 118.1 . . ?
C22 C23 H23 118.1 . . ?
C25 N24 C23 115.78(10) . . ?
N24 C25 C26 124.53(11) . . ?
N24 C25 H25 117.7 . . ?
C26 C25 H25 117.7 . . ?
C21 C26 C25 119.30(11) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?

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
C6 N1 C2 C3 -0.4(3) . . . . ?
N1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C7 -179.62(14) . . . . ?
C3 C4 C5 C6 -0.37(19) . . . . ?
C7 C4 C5 C6 179.70(12) . . . . ?
C2 N1 C6 C5 0.5(2) . . . . ?
C4 C5 C6 N1 -0.1(2) . . . . ?
C5 C4 C7 C8 -80.98(15) . . . . ?
C3 C4 C7 C8 99.10(15) . . . . ?
C4 C7 C8 C13 95.32(14) . . . . ?
C4 C7 C8 C9 -84.95(14) . . . . ?
C13 C8 C9 C10 2.45(17) . . . . ?
C7 C8 C9 C10 -177.29(11) . . . . ?
C8 C9 C10 C11 -0.04(18) . . . . ?
C9 C10 C11 C12 -2.28(17) . . . . ?
C9 C10 C11 C14 175.63(10) . . . . ?
C10 C11 C12 C13 2.20(17) . . . . ?
C14 C11 C12 C13 -175.71(10) . . . . ?
C9 C8 C13 C12 -2.52(17) . . . . ?
C7 C8 C13 C12 177.22(11) . . . . ?
C11 C12 C13 C8 0.20(18) . . . . ?
C10 C11 C14 C19 -144.02(11) . . . . ?
C12 C11 C14 C19 33.83(15) . . . . ?
C10 C11 C14 C15 34.94(15) . . . . ?
C12 C11 C14 C15 -147.21(11) . . . . ?
C19 C14 C15 C16 -0.07(15) . . . . ?
C11 C14 C15 C16 -179.06(10) . . . . ?
C14 C15 C16 C17 0.70(16) . . . . ?
C15 C16 C17 C18 -0.60(16) . . . . ?
C15 C16 C17 C20 -179.68(10) . . . . ?
C16 C17 C18 C19 -0.10(16) . . . . ?
C20 C17 C18 C19 178.99(10) . . . . ?
C17 C18 C19 C14 0.73(16) . . . . ?
C15 C14 C19 C18 -0.63(15) . . . . ?
C11 C14 C19 C18 178.37(10) . . . . ?
C16 C17 C20 C21 -99.89(13) . . . . ?
C18 C17 C20 C21 81.05(13) . . . . ?
C17 C20 C21 C26 -133.03(11) . . . . ?
C17 C20 C21 C22 50.09(15) . . . . ?
C26 C21 C22 C23 -0.69(16) . . . . ?
C20 C21 C22 C23 176.32(10) . . . . ?
C21 C22 C23 N24 0.92(18) . . . . ?
C22 C23 N24 C25 -0.86(17) . . . . ?
C23 N24 C25 C26 0.67(17) . . . . ?
C22 C21 C26 C25 0.50(16) . . . . ?
C20 C21 C26 C25 -176.53(10) . . . . ?
N24 C25 C26 C21 -0.52(18) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.035

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SC4DCM
_database_code_depnum_ccdc_archive 'CCDC 2253375'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University 
Poland
;
_audit_update_record             
;
2023-04-02 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N4'
_chemical_formula_weight         314.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   5.66180(10)
_cell_length_b                   14.6008(2)
_cell_length_c                   19.1251(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.6510(10)
_cell_angle_gamma                90
_cell_volume                     1580.91(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11886
_cell_measurement_theta_min      3.7790
_cell_measurement_theta_max      76.8890

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.633
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66073
_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            18651
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.809
_diffrn_reflns_theta_max         77.187
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3263
_reflns_number_gt                2917
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0411P)²+0.4649P] 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         3263
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.85080(16) -0.07192(6) 0.20913(5) 0.0238(2) Uani 1 1 d . . . . .
C2 C 0.6736(2) -0.09727(8) 0.16484(6) 0.0300(3) Uani 1 1 d . . . . .
H2 H 0.546112 -0.135952 0.177468 0.036 Uiso 1 1 calc R U . . .
N3 N 0.70048(19) -0.06147(7) 0.10194(5) 0.0336(2) Uani 1 1 d . . . . .
C4 C 0.9021(2) -0.01073(8) 0.10663(6) 0.0284(2) Uani 1 1 d . . . . .
H4 H 0.967337 0.023523 0.069287 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9967(2) -0.01591(8) 0.17198(6) 0.0275(2) Uani 1 1 d . . . . .
H5 H 1.136164 0.013452 0.188595 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8676(2) -0.09282(8) 0.28372(6) 0.0299(3) Uani 1 1 d . . . . .
H6A H 1.036061 -0.093776 0.298144 0.036 Uiso 1 1 calc R U . . .
H6B H 0.801645 -0.154609 0.292046 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7371(2) -0.02397(8) 0.32825(6) 0.0253(2) Uani 1 1 d . . . . .
C8 C 0.5217(2) -0.04752(8) 0.35680(6) 0.0274(2) Uani 1 1 d . . . . .
H8 H 0.456404 -0.106276 0.347584 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4003(2) 0.01359(8) 0.39865(6) 0.0263(2) Uani 1 1 d . . . . .
H9 H 0.253616 -0.004224 0.418073 0.032 Uiso 1 1 calc R U . . .
C10 C 0.48975(19) 0.10078(7) 0.41277(5) 0.0221(2) Uani 1 1 d . . . . .
C11 C 0.70730(19) 0.12435(8) 0.38379(6) 0.0254(2) Uani 1 1 d . . . . .
H11 H 0.772899 0.183100 0.392869 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8284(2) 0.06300(8) 0.34196(6) 0.0270(2) Uani 1 1 d . . . . .
H12 H 0.975242 0.080431 0.322427 0.032 Uiso 1 1 calc R U . . .
C13 C 0.34982(18) 0.16705(7) 0.45444(5) 0.0216(2) Uani 1 1 d . . . . .
C14 C 0.1922(2) 0.13710(8) 0.50525(6) 0.0248(2) Uani 1 1 d . . . . .
H14 H 0.183372 0.073674 0.515997 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0485(2) 0.19831(8) 0.54027(6) 0.0246(2) Uani 1 1 d . . . . .
H15 H -0.057345 0.176274 0.574595 0.030 Uiso 1 1 calc R U . . .
C16 C 0.05739(19) 0.29145(7) 0.52580(5) 0.0224(2) Uani 1 1 d . . . . .
C17 C 0.21800(19) 0.32236(8) 0.47634(6) 0.0252(2) Uani 1 1 d . . . . .
H17 H 0.228582 0.385985 0.466484 0.030 Uiso 1 1 calc R U . . .
C18 C 0.36234(19) 0.26134(8) 0.44139(6) 0.0241(2) Uani 1 1 d . . . . .
H18 H 0.471360 0.283774 0.408102 0.029 Uiso 1 1 calc R U . . .
C19 C -0.1112(2) 0.35896(8) 0.55869(6) 0.0256(2) Uani 1 1 d . . . . .
H19A H -0.034160 0.419760 0.561191 0.031 Uiso 1 1 calc R U . . .
H19B H -0.253175 0.364841 0.528334 0.031 Uiso 1 1 calc R U . . .
N20 N -0.18431(16) 0.33223(6) 0.62878(5) 0.0226(2) Uani 1 1 d . . . . .
C21 C -0.3894(2) 0.29057(7) 0.64558(6) 0.0253(2) Uani 1 1 d . . . . .
H21 H -0.511071 0.276784 0.612624 0.030 Uiso 1 1 calc R U . . .
N22 N -0.40172(18) 0.27119(7) 0.71284(5) 0.0290(2) Uani 1 1 d . . . . .
C23 C -0.1915(2) 0.30265(8) 0.74034(6) 0.0279(2) Uani 1 1 d . . . . .
H23 H -0.147350 0.298668 0.788315 0.034 Uiso 1 1 calc R U . . .
C24 C -0.0546(2) 0.34035(8) 0.68964(6) 0.0261(2) Uani 1 1 d . . . . .
H24 H 0.098004 0.366624 0.695210 0.031 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 1.3570(15) . ?
N1 C5 1.3672(14) . ?
N1 C6 1.4608(14) . ?
C2 N3 1.3219(17) . ?
C2 H2 0.9500 . ?
N3 C4 1.3630(16) . ?
C4 C5 1.3564(17) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.5152(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.3852(16) . ?
C7 C12 1.3946(16) . ?
C8 C9 1.3863(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3953(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3994(15) . ?
C10 C13 1.4878(14) . ?
C11 C12 1.3874(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3970(15) . ?
C13 C18 1.4010(15) . ?
C14 C15 1.3863(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3889(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3946(16) . ?
C16 C19 1.5137(15) . ?
C17 C18 1.3859(15) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N20 1.4605(14) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N20 C21 1.3529(14) . ?
N20 C24 1.3745(14) . ?
C21 N22 1.3195(15) . ?
C21 H21 0.9500 . ?
N22 C23 1.3750(16) . ?
C23 C24 1.3642(17) . ?
C23 H23 0.9500 . ?
C24 H24 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 106.59(10) . . ?
C2 N1 C6 126.30(10) . . ?
C5 N1 C6 126.82(10) . . ?
N3 C2 N1 111.61(10) . . ?
N3 C2 H2 124.2 . . ?
N1 C2 H2 124.2 . . ?
C2 N3 C4 105.07(10) . . ?
C5 C4 N3 110.60(10) . . ?
C5 C4 H4 124.7 . . ?
N3 C4 H4 124.7 . . ?
C4 C5 N1 106.12(10) . . ?
C4 C5 H5 126.9 . . ?
N1 C5 H5 126.9 . . ?
N1 C6 C7 112.56(9) . . ?
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 . . ?
C8 C7 C12 118.55(10) . . ?
C8 C7 C6 119.60(10) . . ?
C12 C7 C6 121.85(10) . . ?
C7 C8 C9 120.83(11) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 121.18(10) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 117.83(10) . . ?
C9 C10 C13 120.19(10) . . ?
C11 C10 C13 121.91(10) . . ?
C12 C11 C10 120.84(10) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 120.78(10) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 117.75(10) . . ?
C14 C13 C10 121.15(10) . . ?
C18 C13 C10 121.02(10) . . ?
C15 C14 C13 121.15(10) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.81(10) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 118.51(10) . . ?
C15 C16 C19 122.03(10) . . ?
C17 C16 C19 119.35(10) . . ?
C18 C17 C16 120.79(10) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 120.96(10) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
N20 C19 C16 113.20(9) . . ?
N20 C19 H19A 108.9 . . ?
C16 C19 H19A 108.9 . . ?
N20 C19 H19B 108.9 . . ?
C16 C19 H19B 108.9 . . ?
H19A C19 H19B 107.8 . . ?
C21 N20 C24 106.83(9) . . ?
C21 N20 C19 126.25(9) . . ?
C24 N20 C19 126.85(9) . . ?
N22 C21 N20 112.52(10) . . ?
N22 C21 H21 123.7 . . ?
N20 C21 H21 123.7 . . ?
C21 N22 C23 104.25(10) . . ?
C24 C23 N22 111.06(10) . . ?
C24 C23 H23 124.5 . . ?
N22 C23 H23 124.5 . . ?
C23 C24 N20 105.34(10) . . ?
C23 C24 H24 127.3 . . ?
N20 C24 H24 127.3 . . ?

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 0.68(13) . . . . ?
C6 N1 C2 N3 174.86(10) . . . . ?
N1 C2 N3 C4 -0.46(13) . . . . ?
C2 N3 C4 C5 0.06(13) . . . . ?
N3 C4 C5 N1 0.35(13) . . . . ?
C2 N1 C5 C4 -0.61(12) . . . . ?
C6 N1 C5 C4 -174.75(10) . . . . ?
C2 N1 C6 C7 -85.61(14) . . . . ?
C5 N1 C6 C7 87.41(13) . . . . ?
N1 C6 C7 C8 104.38(12) . . . . ?
N1 C6 C7 C12 -76.05(14) . . . . ?
C12 C7 C8 C9 -0.61(17) . . . . ?
C6 C7 C8 C9 178.97(10) . . . . ?
C7 C8 C9 C10 0.62(17) . . . . ?
C8 C9 C10 C11 -0.56(16) . . . . ?
C8 C9 C10 C13 176.48(10) . . . . ?
C9 C10 C11 C12 0.51(16) . . . . ?
C13 C10 C11 C12 -176.47(10) . . . . ?
C10 C11 C12 C7 -0.53(17) . . . . ?
C8 C7 C12 C11 0.57(17) . . . . ?
C6 C7 C12 C11 -179.00(10) . . . . ?
C9 C10 C13 C14 29.42(15) . . . . ?
C11 C10 C13 C14 -153.67(11) . . . . ?
C9 C10 C13 C18 -147.10(11) . . . . ?
C11 C10 C13 C18 29.81(15) . . . . ?
C18 C13 C14 C15 1.68(16) . . . . ?
C10 C13 C14 C15 -174.95(10) . . . . ?
C13 C14 C15 C16 -0.05(17) . . . . ?
C14 C15 C16 C17 -1.42(16) . . . . ?
C14 C15 C16 C19 174.80(10) . . . . ?
C15 C16 C17 C18 1.24(16) . . . . ?
C19 C16 C17 C18 -175.08(10) . . . . ?
C16 C17 C18 C13 0.42(17) . . . . ?
C14 C13 C18 C17 -1.86(16) . . . . ?
C10 C13 C18 C17 174.78(10) . . . . ?
C15 C16 C19 N20 31.45(15) . . . . ?
C17 C16 C19 N20 -152.36(10) . . . . ?
C16 C19 N20 C21 -99.31(12) . . . . ?
C16 C19 N20 C24 77.29(13) . . . . ?
C24 N20 C21 N22 0.02(13) . . . . ?
C19 N20 C21 N22 177.18(10) . . . . ?
N20 C21 N22 C23 0.08(12) . . . . ?
C21 N22 C23 C24 -0.15(13) . . . . ?
N22 C23 C24 N20 0.16(13) . . . . ?
C21 N20 C24 C23 -0.11(12) . . . . ?
C19 N20 C24 C23 -177.24(10) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_1MeOH
_database_code_depnum_ccdc_archive 'CCDC 2253374'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University 
Poland
;
_audit_update_record             
;
2023-04-02 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2'
_chemical_formula_weight         336.42

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      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                   5.76800(5)
_cell_length_b                   9.98210(10)
_cell_length_c                   15.60390(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.4410(10)
_cell_angle_gamma                90
_cell_volume                     883.546(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23887
_cell_measurement_theta_min      2.8640
_cell_measurement_theta_max      77.1210

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.570
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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            29193
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.880
_diffrn_reflns_theta_max         77.323
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3501
_reflns_number_gt                3451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_max     0.896
_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       '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-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0403P)²+0.1306P] 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_abs_structure_details 
;
 Flack x determined using 1548 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 ?
_refine_ls_number_reflns         3501
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.5171(3) 0.59222(16) 0.42598(9) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.7218(3) 0.5253(2) 0.43555(11) 0.0326(4) Uani 1 1 d . . . . .
H2 H 0.806128 0.527401 0.388606 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8182(3) 0.45364(18) 0.50912(11) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.964252 0.408372 0.511908 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6991(3) 0.44832(16) 0.57929(10) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.4852(3) 0.51520(17) 0.56968(10) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.395367 0.513079 0.615029 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4033(3) 0.58522(18) 0.49340(11) 0.0286(3) Uani 1 1 d . . . . .
H6 H 0.257292 0.631105 0.488711 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8103(3) 0.37396(18) 0.66132(10) 0.0253(3) Uani 1 1 d . . . . .
H7B H 0.806715 0.276786 0.648445 0.030 Uiso 1 1 calc R U . . .
H7A H 0.977726 0.401070 0.676937 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6931(3) 0.39730(16) 0.73929(9) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.7866(3) 0.48626(16) 0.80529(9) 0.0220(3) Uani 1 1 d . . . . .
H9 H 0.928358 0.532666 0.801790 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6762(3) 0.50848(16) 0.87631(9) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.744775 0.568694 0.920923 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4652(2) 0.44305(15) 0.88275(9) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.3720(3) 0.35402(15) 0.81601(10) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.228548 0.308810 0.818680 0.025 Uiso 1 1 calc R U . . .
C13 C 0.4845(3) 0.33036(16) 0.74607(10) 0.0224(3) Uani 1 1 d . . . . .
H13 H 0.418950 0.267992 0.702344 0.027 Uiso 1 1 calc R U . . .
C14 C 0.3428(2) 0.46600(15) 0.95734(9) 0.0187(3) Uani 1 1 d . . . . .
C15 C 0.3430(3) 0.59186(16) 0.99685(10) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.424119 0.664188 0.975930 0.026 Uiso 1 1 calc R U . . .
C16 C 0.2266(3) 0.61269(15) 1.06603(10) 0.0215(3) Uani 1 1 d . . . . .
H16 H 0.231535 0.698717 1.092329 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1027(2) 0.50968(15) 1.09764(9) 0.0197(3) Uani 1 1 d . . . . .
C18 C 0.1013(3) 0.38389(15) 1.05841(9) 0.0203(3) Uani 1 1 d . . . . .
H18 H 0.018906 0.311849 1.079060 0.024 Uiso 1 1 calc R U . . .
C19 C 0.2193(3) 0.36313(15) 0.98957(9) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.215817 0.276787 0.963764 0.024 Uiso 1 1 calc R U . . .
C20 C -0.0360(3) 0.53738(16) 1.16992(11) 0.0247(3) Uani 1 1 d . . . . .
H20A H 0.043267 0.610371 1.207099 0.030 Uiso 1 1 calc R U . . .
H20B H -0.195101 0.569530 1.143272 0.030 Uiso 1 1 calc R U . . .
C21 C -0.0619(3) 0.41877(15) 1.22667(9) 0.0210(3) Uani 1 1 d . . . . .
C22 C 0.1199(3) 0.37997(17) 1.29341(10) 0.0253(3) Uani 1 1 d . . . . .
H22 H 0.264477 0.427963 1.303759 0.030 Uiso 1 1 calc R U . . .
C23 C 0.0873(3) 0.27043(18) 1.34462(11) 0.0288(4) Uani 1 1 d . . . . .
H23 H 0.213139 0.245776 1.390006 0.035 Uiso 1 1 calc R U . . .
N24 N -0.1099(3) 0.19746(15) 1.33408(9) 0.0301(3) Uani 1 1 d . . . . .
C25 C -0.2831(3) 0.23560(18) 1.26990(11) 0.0303(4) Uani 1 1 d . . . . .
H25 H -0.425462 0.185492 1.261080 0.036 Uiso 1 1 calc R U . . .
C26 C -0.2684(3) 0.34338(17) 1.21545(11) 0.0268(3) Uani 1 1 d . . . . .
H26 H -0.397817 0.365772 1.170880 0.032 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 C6 1.339(2) . ?
N1 C2 1.341(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 C7 1.518(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.513(2) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 C9 1.392(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(2) . ?
C11 C14 1.4844(19) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.395(2) . ?
C14 C15 1.399(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(2) . ?
C17 C20 1.521(2) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.502(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.392(2) . ?
C21 C26 1.393(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 N24 1.336(2) . ?
C23 H23 0.9500 . ?
N24 C25 1.335(2) . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 H26 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
C6 N1 C2 115.69(14) . . ?
N1 C2 C3 124.34(15) . . ?
N1 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
C2 C3 C4 119.40(15) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 116.86(14) . . ?
C5 C4 C7 123.93(14) . . ?
C3 C4 C7 119.20(14) . . ?
C4 C5 C6 119.54(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 124.16(16) . . ?
N1 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
C8 C7 C4 114.89(13) . . ?
C8 C7 H7B 108.5 . . ?
C4 C7 H7B 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C4 C7 H7A 108.5 . . ?
H7B C7 H7A 107.5 . . ?
C9 C8 C13 118.19(14) . . ?
C9 C8 C7 121.55(14) . . ?
C13 C8 C7 120.25(14) . . ?
C10 C9 C8 121.24(14) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.75(14) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 117.65(13) . . ?
C12 C11 C14 120.54(13) . . ?
C10 C11 C14 121.81(13) . . ?
C13 C12 C11 121.46(14) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C8 120.68(14) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C19 C14 C15 117.50(13) . . ?
C19 C14 C11 121.05(13) . . ?
C15 C14 C11 121.44(13) . . ?
C16 C15 C14 121.07(14) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.14(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 118.10(13) . . ?
C16 C17 C20 120.06(14) . . ?
C18 C17 C20 121.77(14) . . ?
C19 C18 C17 120.61(14) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 121.57(14) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C21 C20 C17 114.56(13) . . ?
C21 C20 H20A 108.6 . . ?
C17 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C17 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C26 117.04(15) . . ?
C22 C21 C20 121.22(15) . . ?
C26 C21 C20 121.73(14) . . ?
C23 C22 C21 119.22(15) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
N24 C23 C22 124.07(15) . . ?
N24 C23 H23 118.0 . . ?
C22 C23 H23 118.0 . . ?
C25 N24 C23 116.20(15) . . ?
N24 C25 C26 124.18(16) . . ?
N24 C25 H25 117.9 . . ?
C26 C25 H25 117.9 . . ?
C25 C26 C21 119.29(15) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?

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
C6 N1 C2 C3 -0.7(3) . . . . ?
N1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C2 C3 C4 C7 -177.64(16) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C7 C4 C5 C6 177.20(16) . . . . ?
C2 N1 C6 C5 0.3(3) . . . . ?
C4 C5 C6 N1 0.8(3) . . . . ?
C5 C4 C7 C8 -10.3(2) . . . . ?
C3 C4 C7 C8 168.22(15) . . . . ?
C4 C7 C8 C9 -100.40(17) . . . . ?
C4 C7 C8 C13 78.81(19) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C10 179.20(14) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C9 C10 C11 C14 -179.38(14) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C14 C11 C12 C13 -179.51(13) . . . . ?
C11 C12 C13 C8 -1.3(2) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
C7 C8 C13 C12 -178.10(14) . . . . ?
C12 C11 C14 C19 33.7(2) . . . . ?
C10 C11 C14 C19 -146.14(15) . . . . ?
C12 C11 C14 C15 -145.01(15) . . . . ?
C10 C11 C14 C15 35.1(2) . . . . ?
C19 C14 C15 C16 0.7(2) . . . . ?
C11 C14 C15 C16 179.48(13) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C15 C16 C17 C20 -176.23(14) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C20 C17 C18 C19 176.62(14) . . . . ?
C17 C18 C19 C14 0.1(2) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?
C11 C14 C19 C18 -179.05(13) . . . . ?
C16 C17 C20 C21 -151.97(15) . . . . ?
C18 C17 C20 C21 31.0(2) . . . . ?
C17 C20 C21 C22 79.85(18) . . . . ?
C17 C20 C21 C26 -100.61(17) . . . . ?
C26 C21 C22 C23 -0.1(2) . . . . ?
C20 C21 C22 C23 179.48(14) . . . . ?
C21 C22 C23 N24 0.3(2) . . . . ?
C22 C23 N24 C25 -0.3(2) . . . . ?
C23 N24 C25 C26 0.1(2) . . . . ?
N24 C25 C26 C21 0.1(2) . . . . ?
C22 C21 C26 C25 -0.1(2) . . . . ?
C20 C21 C26 C25 -179.65(14) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2253376'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University 
Poland
;
_audit_update_record             
;
2023-04-02 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N4'
_chemical_formula_weight         314.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      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                   18.2880(5)
_cell_length_b                   7.9130(2)
_cell_length_c                   22.3941(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3240.72(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7291
_cell_measurement_theta_min      3.9080
_cell_measurement_theta_max      67.0290

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   0.66756
_exptl_transmission_factor_max   1.00000
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.618
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.624
_oxdiff_exptl_absorpt_empirical_full_max 1.822
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_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            27548
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.948
_diffrn_reflns_theta_max         68.576
_diffrn_reflns_theta_full        67.684
_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             2985
_reflns_number_gt                2368
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0430P)²+1.0214P] 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         2985
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.89668(7) -0.07147(16) 0.23956(5) 0.0326(3) Uani 1 1 d . . . . .
N3 N 0.80170(8) -0.18310(18) 0.19181(6) 0.0412(3) Uani 1 1 d . . . . .
N22 N 0.94191(8) 1.19826(18) 0.63404(6) 0.0425(4) Uani 1 1 d . . . . .
N20 N 0.86932(7) 1.03909(16) 0.57820(6) 0.0337(3) Uani 1 1 d . . . . .
C13 C 0.86345(8) 0.54682(19) 0.43402(7) 0.0312(3) Uani 1 1 d . . . . .
C4 C 0.82327(9) -0.2879(2) 0.23732(7) 0.0389(4) Uani 1 1 d . . . . .
H4 H 0.800856 -0.393021 0.246585 0.047 Uiso 1 1 calc R U . . .
C17 C 0.86640(8) 0.6622(2) 0.53426(7) 0.0330(3) Uani 1 1 d . . . . .
H17 H 0.881742 0.652623 0.574653 0.040 Uiso 1 1 calc R U . . .
C21 C 0.87999(9) 1.1129(2) 0.63158(7) 0.0405(4) Uani 1 1 d . . . . .
H21 H 0.846627 1.104548 0.663956 0.049 Uiso 1 1 calc R U . . .
C8 C 0.86028(8) 0.2528(2) 0.30066(7) 0.0350(4) Uani 1 1 d . . . . .
H8 H 0.828037 0.224923 0.268895 0.042 Uiso 1 1 calc R U . . .
C18 C 0.88532(8) 0.5373(2) 0.49372(7) 0.0324(3) Uani 1 1 d . . . . .
H18 H 0.913628 0.443567 0.506736 0.039 Uiso 1 1 calc R U . . .
C10 C 0.88506(8) 0.41612(19) 0.38986(7) 0.0314(3) Uani 1 1 d . . . . .
C12 C 0.97413(8) 0.2170(2) 0.35131(7) 0.0347(4) Uani 1 1 d . . . . .
H12 H 1.020603 0.164269 0.354835 0.042 Uiso 1 1 calc R U . . .
C15 C 0.80305(9) 0.8109(2) 0.45750(7) 0.0383(4) Uani 1 1 d . . . . .
H15 H 0.774942 0.905050 0.444607 0.046 Uiso 1 1 calc R U . . .
C5 C 0.88106(9) -0.2211(2) 0.26739(7) 0.0365(4) Uani 1 1 d . . . . .
H5 H 0.905551 -0.268559 0.300833 0.044 Uiso 1 1 calc R U . . .
C11 C 0.95303(8) 0.3357(2) 0.39317(7) 0.0347(4) Uani 1 1 d . . . . .
H11 H 0.985407 0.363244 0.424882 0.042 Uiso 1 1 calc R U . . .
C7 C 0.92844(8) 0.1734(2) 0.30412(7) 0.0320(3) Uani 1 1 d . . . . .
C6 C 0.95331(8) 0.0500(2) 0.25667(7) 0.0355(4) Uani 1 1 d . . . . .
H6A H 0.968637 0.114070 0.220815 0.043 Uiso 1 1 calc R U . . .
H6B H 0.996461 -0.012508 0.271640 0.043 Uiso 1 1 calc R U . . .
C9 C 0.83896(8) 0.3708(2) 0.34247(7) 0.0338(4) Uani 1 1 d . . . . .
H9 H 0.792208 0.422244 0.339118 0.041 Uiso 1 1 calc R U . . .
C23 C 0.97209(9) 1.1778(2) 0.57858(7) 0.0382(4) Uani 1 1 d . . . . .
H23 H 1.017574 1.224364 0.566396 0.046 Uiso 1 1 calc R U . . .
C14 C 0.82116(8) 0.6856(2) 0.41695(7) 0.0353(4) Uani 1 1 d . . . . .
H14 H 0.804529 0.694118 0.376876 0.042 Uiso 1 1 calc R U . . .
C16 C 0.82527(8) 0.8012(2) 0.51663(7) 0.0348(4) Uani 1 1 d . . . . .
C2 C 0.84747(9) -0.0549(2) 0.19479(7) 0.0377(4) Uani 1 1 d . . . . .
H2 H 0.846101 0.039057 0.168388 0.045 Uiso 1 1 calc R U . . .
C19 C 0.80509(8) 0.9385(2) 0.56032(8) 0.0400(4) Uani 1 1 d . . . . .
H19A H 0.768259 1.013922 0.541876 0.048 Uiso 1 1 calc R U . . .
H19B H 0.782818 0.886821 0.596230 0.048 Uiso 1 1 calc R U . . .
C24 C 0.92823(9) 1.0819(2) 0.54339(7) 0.0368(4) Uani 1 1 d . . . . .
H24 H 0.936580 1.050792 0.502984 0.044 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 1.354(2) . ?
N1 C5 1.368(2) . ?
N1 C6 1.4641(19) . ?
N3 C2 1.317(2) . ?
N3 C4 1.372(2) . ?
N22 C21 1.320(2) . ?
N22 C23 1.369(2) . ?
N20 C21 1.345(2) . ?
N20 C24 1.372(2) . ?
N20 C19 1.474(2) . ?
C13 C14 1.396(2) . ?
C13 C18 1.398(2) . ?
C13 C10 1.484(2) . ?
C4 C5 1.360(2) . ?
C4 H4 0.9500 . ?
C17 C18 1.386(2) . ?
C17 C16 1.390(2) . ?
C17 H17 0.9500 . ?
C21 H21 0.9500 . ?
C8 C9 1.378(2) . ?
C8 C7 1.398(2) . ?
C8 H8 0.9500 . ?
C18 H18 0.9500 . ?
C10 C11 1.399(2) . ?
C10 C9 1.402(2) . ?
C12 C11 1.382(2) . ?
C12 C7 1.391(2) . ?
C12 H12 0.9500 . ?
C15 C14 1.385(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C7 C6 1.513(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 H9 0.9500 . ?
C23 C24 1.356(2) . ?
C23 H23 0.9500 . ?
C14 H14 0.9500 . ?
C16 C19 1.508(2) . ?
C2 H2 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C24 H24 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 106.42(13) . . ?
C2 N1 C6 126.89(13) . . ?
C5 N1 C6 126.64(13) . . ?
C2 N3 C4 104.22(14) . . ?
C21 N22 C23 104.33(13) . . ?
C21 N20 C24 106.49(13) . . ?
C21 N20 C19 126.28(14) . . ?
C24 N20 C19 127.19(13) . . ?
C14 C13 C18 117.57(14) . . ?
C14 C13 C10 120.86(14) . . ?
C18 C13 C10 121.56(14) . . ?
C5 C4 N3 110.85(15) . . ?
C5 C4 H4 124.6 . . ?
N3 C4 H4 124.6 . . ?
C18 C17 C16 120.90(14) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N22 C21 N20 112.58(15) . . ?
N22 C21 H21 123.7 . . ?
N20 C21 H21 123.7 . . ?
C9 C8 C7 121.27(14) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C17 C18 C13 121.10(15) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C11 C10 C9 117.26(14) . . ?
C11 C10 C13 121.22(13) . . ?
C9 C10 C13 121.50(14) . . ?
C11 C12 C7 121.08(14) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C14 C15 C16 121.09(15) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C4 C5 N1 105.85(14) . . ?
C4 C5 H5 127.1 . . ?
N1 C5 H5 127.1 . . ?
C12 C11 C10 121.44(14) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C12 C7 C8 117.80(14) . . ?
C12 C7 C6 120.87(14) . . ?
C8 C7 C6 121.28(14) . . ?
N1 C6 C7 113.25(12) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C9 C10 121.15(14) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C24 C23 N22 110.80(15) . . ?
C24 C23 H23 124.6 . . ?
N22 C23 H23 124.6 . . ?
C15 C14 C13 121.08(15) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C15 C16 C17 118.24(15) . . ?
C15 C16 C19 120.53(15) . . ?
C17 C16 C19 121.23(15) . . ?
N3 C2 N1 112.65(15) . . ?
N3 C2 H2 123.7 . . ?
N1 C2 H2 123.7 . . ?
N20 C19 C16 111.72(12) . . ?
N20 C19 H19A 109.3 . . ?
C16 C19 H19A 109.3 . . ?
N20 C19 H19B 109.3 . . ?
C16 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C23 C24 N20 105.79(14) . . ?
C23 C24 H24 127.1 . . ?
N20 C24 H24 127.1 . . ?

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
C2 N3 C4 C5 0.58(19) . . . . ?
C23 N22 C21 N20 0.32(19) . . . . ?
C24 N20 C21 N22 -0.87(19) . . . . ?
C19 N20 C21 N22 -178.41(15) . . . . ?
C16 C17 C18 C13 -0.3(2) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C10 C13 C18 C17 178.35(14) . . . . ?
C14 C13 C10 C11 144.67(15) . . . . ?
C18 C13 C10 C11 -34.4(2) . . . . ?
C14 C13 C10 C9 -34.0(2) . . . . ?
C18 C13 C10 C9 146.93(15) . . . . ?
N3 C4 C5 N1 -0.72(18) . . . . ?
C2 N1 C5 C4 0.55(17) . . . . ?
C6 N1 C5 C4 178.02(14) . . . . ?
C7 C12 C11 C10 0.2(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C13 C10 C11 C12 -178.37(15) . . . . ?
C11 C12 C7 C8 -0.4(2) . . . . ?
C11 C12 C7 C6 176.86(15) . . . . ?
C9 C8 C7 C12 0.2(2) . . . . ?
C9 C8 C7 C6 -177.11(15) . . . . ?
C2 N1 C6 C7 91.62(19) . . . . ?
C5 N1 C6 C7 -85.35(18) . . . . ?
C12 C7 C6 N1 137.78(15) . . . . ?
C8 C7 C6 N1 -45.0(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C11 C10 C9 C8 -0.6(2) . . . . ?
C13 C10 C9 C8 178.11(15) . . . . ?
C21 N22 C23 C24 0.36(19) . . . . ?
C16 C15 C14 C13 -1.1(2) . . . . ?
C18 C13 C14 C15 1.5(2) . . . . ?
C10 C13 C14 C15 -177.68(14) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C19 -179.93(15) . . . . ?
C18 C17 C16 C15 0.6(2) . . . . ?
C18 C17 C16 C19 -179.39(14) . . . . ?
C4 N3 C2 N1 -0.22(19) . . . . ?
C5 N1 C2 N3 -0.21(18) . . . . ?
C6 N1 C2 N3 -177.67(14) . . . . ?
C21 N20 C19 C16 -148.02(16) . . . . ?
C24 N20 C19 C16 34.9(2) . . . . ?
C15 C16 C19 N20 -110.10(17) . . . . ?
C17 C16 C19 N20 69.9(2) . . . . ?
N22 C23 C24 N20 -0.88(19) . . . . ?
C21 N20 C24 C23 1.03(17) . . . . ?
C19 N20 C24 C23 178.54(15) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.035

