# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

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

data_cu_PGIF165
_database_code_depnum_ccdc_archive 'CCDC 1919005'
loop_
_audit_author_name
_audit_author_address
'Kinga Suwinska'
;Cardinal Stefan Wyszynski University in Warsaw
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N2 O3'
_chemical_formula_sum            'C19 H20 N2 O3'
_chemical_formula_weight         324.37

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                   16.000(2)
_cell_length_b                   6.7252(9)
_cell_length_c                   30.665(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.080(10)
_cell_angle_gamma                90
_cell_volume                     3267.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1929
_cell_measurement_theta_min      2.9109
_cell_measurement_theta_max      59.7333

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   I\mS
_diffrn_measurement_device_type  'D8 VENTURE DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            25438
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_av_R_equivalents  0.2154
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         68.370
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2988
_reflns_number_gt                1301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0677P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1769
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3422(2) 0.0681(4) 0.70734(10) 0.0728(9) Uani 1 1 d . . . . .
H1O H 0.365835 0.127373 0.729003 0.109 Uiso 1 1 calc R U . . .
C1 C 0.3281(3) 0.4712(6) 0.73545(14) 0.0575(11) Uani 1 1 d . . . . .
H1 H 0.321063 0.603726 0.742769 0.069 Uiso 1 1 calc R U . . .
O2 O 0.6321(2) 0.4145(5) 0.92234(10) 0.0831(10) Uani 1 1 d . . . . .
C2 C 0.2764(3) 0.3899(5) 0.69823(12) 0.0534(10) Uani 1 1 d . . . . .
N1 N 0.3845(2) 0.3663(4) 0.75935(11) 0.0563(9) Uani 1 1 d . . . . .
N2 N 0.1268(2) 0.1603(5) 0.58551(11) 0.0650(10) Uani 1 1 d . . . . .
C15 C 0.5806(3) 0.2831(8) 0.89753(16) 0.0735(13) Uani 1 1 d . . . . .
C14 C 0.5343(3) 0.3887(6) 0.85985(14) 0.0587(11) Uani 1 1 d . . . . .
C13 C 0.4766(3) 0.3173(6) 0.82628(14) 0.0597(11) Uani 1 1 d . . . . .
H13 H 0.462304 0.183166 0.824901 0.072 Uiso 1 1 calc R U . . .
O3 O 0.5780(2) 0.1103(5) 0.90865(11) 0.0932(11) Uani 1 1 d . . . . .
C3 C 0.2846(3) 0.1902(5) 0.68409(13) 0.0533(10) Uani 1 1 d . . . . .
C12 C 0.4400(3) 0.4479(5) 0.79462(14) 0.0562(11) Uani 1 1 d . . . . .
C4 C 0.2366(3) 0.1170(6) 0.64708(14) 0.0588(11) Uani 1 1 d . . . . .
H4 H 0.244918 -0.013267 0.638454 0.071 Uiso 1 1 calc R U . . .
C19 C 0.4634(3) 0.6497(5) 0.79789(15) 0.0669(12) Uani 1 1 d . . . . .
H19 H 0.437588 0.739224 0.777109 0.080 Uiso 1 1 calc R U . . .
C5 C 0.1756(3) 0.2336(6) 0.62199(13) 0.0535(10) Uani 1 1 d . . . . .
C18 C 0.5236(3) 0.7182(6) 0.83115(16) 0.0697(13) Uani 1 1 d . . . . .
H18 H 0.539912 0.851077 0.832255 0.084 Uiso 1 1 calc R U . . .
C6 C 0.1663(3) 0.4329(6) 0.63580(14) 0.0618(11) Uani 1 1 d . . . . .
H6 H 0.126755 0.515499 0.619690 0.074 Uiso 1 1 calc R U . . .
C17 C 0.5592(3) 0.5853(6) 0.86273(15) 0.0627(11) Uani 1 1 d . . . . .
C7 C 0.2148(3) 0.5034(6) 0.67238(15) 0.0604(11) Uani 1 1 d . . . . .
H7 H 0.206649 0.634087 0.680755 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6251(3) 0.6092(6) 0.90191(16) 0.0769(13) Uani 1 1 d . . . . .
H16A H 0.678492 0.649489 0.893070 0.092 Uiso 1 1 calc R U . . .
H16B H 0.608091 0.707916 0.921988 0.092 Uiso 1 1 calc R U . . .
C8 C 0.1387(3) -0.0408(6) 0.56929(16) 0.0750(13) Uani 1 1 d . . . . .
H8A H 0.086102 -0.086303 0.552633 0.090 Uiso 1 1 calc R U . . .
H8B H 0.152467 -0.129399 0.594220 0.090 Uiso 1 1 calc R U . . .
C9 C 0.2074(4) -0.0522(7) 0.54052(17) 0.0955(17) Uani 1 1 d . . . . .
H9A H 0.216833 -0.188564 0.533369 0.143 Uiso 1 1 calc R U . . .
H9B H 0.258503 0.003224 0.555943 0.143 Uiso 1 1 calc R U . . .
H9C H 0.190782 0.021615 0.513919 0.143 Uiso 1 1 calc R U . . .
C10 C 0.0708(3) 0.2888(7) 0.55595(16) 0.0821(14) Uani 1 1 d . . . . .
H10A H 0.039625 0.374133 0.573455 0.098 Uiso 1 1 calc R U . . .
H10B H 0.030252 0.206662 0.537579 0.098 Uiso 1 1 calc R U . . .
C11 C 0.1172(4) 0.4174(8) 0.52663(18) 0.117(2) Uani 1 1 d . . . . .
H11A H 0.135877 0.336632 0.504057 0.176 Uiso 1 1 calc R U . . .
H11B H 0.165166 0.477807 0.543966 0.176 Uiso 1 1 calc R U . . .
H11C H 0.080020 0.519185 0.513302 0.176 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.359(4) . ?
O1 H1O 0.8200 . ?
C1 N1 1.290(5) . ?
C1 C2 1.421(5) . ?
C1 H1 0.9300 . ?
O2 C15 1.365(5) . ?
O2 C16 1.449(5) . ?
C2 C7 1.402(6) . ?
C2 C3 1.423(5) . ?
N1 C12 1.410(5) . ?
N2 C5 1.363(5) . ?
N2 C8 1.462(5) . ?
N2 C10 1.464(5) . ?
C15 O3 1.214(5) . ?
C15 C14 1.465(6) . ?
C14 C13 1.370(6) . ?
C14 C17 1.381(5) . ?
C13 C12 1.377(5) . ?
C13 H13 0.9300 . ?
C3 C4 1.369(5) . ?
C12 C19 1.408(5) . ?
C4 C5 1.397(5) . ?
C4 H4 0.9300 . ?
C19 C18 1.380(6) . ?
C19 H19 0.9300 . ?
C5 C6 1.419(5) . ?
C18 C17 1.381(6) . ?
C18 H18 0.9300 . ?
C6 C7 1.357(6) . ?
C6 H6 0.9300 . ?
C17 C16 1.492(6) . ?
C7 H7 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C8 C9 1.506(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.515(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1O 109.5 . . ?
N1 C1 C2 121.8(4) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C15 O2 C16 109.9(4) . . ?
C7 C2 C1 121.9(4) . . ?
C7 C2 C3 115.4(4) . . ?
C1 C2 C3 122.7(4) . . ?
C1 N1 C12 122.5(3) . . ?
C5 N2 C8 121.8(4) . . ?
C5 N2 C10 121.6(3) . . ?
C8 N2 C10 115.7(4) . . ?
O3 C15 O2 120.4(5) . . ?
O3 C15 C14 130.7(5) . . ?
O2 C15 C14 108.9(4) . . ?
C13 C14 C17 122.8(4) . . ?
C13 C14 C15 129.5(4) . . ?
C17 C14 C15 107.7(4) . . ?
C14 C13 C12 118.8(4) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
O1 C3 C4 118.5(3) . . ?
O1 C3 C2 119.6(4) . . ?
C4 C3 C2 121.8(4) . . ?
C13 C12 C19 118.8(4) . . ?
C13 C12 N1 116.9(3) . . ?
C19 C12 N1 124.2(4) . . ?
C3 C4 C5 121.4(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C18 C19 C12 121.7(4) . . ?
C18 C19 H19 119.1 . . ?
C12 C19 H19 119.1 . . ?
N2 C5 C4 121.6(4) . . ?
N2 C5 C6 121.0(4) . . ?
C4 C5 C6 117.4(4) . . ?
C19 C18 C17 118.6(4) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C18 C17 C14 119.2(4) . . ?
C18 C17 C16 132.1(4) . . ?
C14 C17 C16 108.7(4) . . ?
C6 C7 C2 123.5(4) . . ?
C6 C7 H7 118.2 . . ?
C2 C7 H7 118.2 . . ?
O2 C16 C17 104.7(3) . . ?
O2 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
O2 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
N2 C8 C9 112.8(4) . . ?
N2 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 113.3(4) . . ?
N2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C7 179.6(4) . . . . ?
N1 C1 C2 C3 -1.7(6) . . . . ?
C2 C1 N1 C12 175.8(4) . . . . ?
C16 O2 C15 O3 179.0(5) . . . . ?
C16 O2 C15 C14 -2.0(5) . . . . ?
O3 C15 C14 C13 -1.7(8) . . . . ?
O2 C15 C14 C13 179.4(4) . . . . ?
O3 C15 C14 C17 178.9(5) . . . . ?
O2 C15 C14 C17 0.0(5) . . . . ?
C17 C14 C13 C12 -1.8(6) . . . . ?
C15 C14 C13 C12 178.8(4) . . . . ?
C7 C2 C3 O1 -179.4(4) . . . . ?
C1 C2 C3 O1 1.8(5) . . . . ?
C7 C2 C3 C4 1.6(5) . . . . ?
C1 C2 C3 C4 -177.2(4) . . . . ?
C14 C13 C12 C19 0.1(6) . . . . ?
C14 C13 C12 N1 176.5(4) . . . . ?
C1 N1 C12 C13 158.7(4) . . . . ?
C1 N1 C12 C19 -25.1(6) . . . . ?
O1 C3 C4 C5 179.2(4) . . . . ?
C2 C3 C4 C5 -1.8(6) . . . . ?
C13 C12 C19 C18 2.0(6) . . . . ?
N1 C12 C19 C18 -174.2(4) . . . . ?
C8 N2 C5 C4 -3.3(6) . . . . ?
C10 N2 C5 C4 -171.8(4) . . . . ?
C8 N2 C5 C6 176.4(4) . . . . ?
C10 N2 C5 C6 8.0(6) . . . . ?
C3 C4 C5 N2 -178.9(4) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C12 C19 C18 C17 -2.4(6) . . . . ?
N2 C5 C6 C7 179.4(4) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
C19 C18 C17 C14 0.7(6) . . . . ?
C19 C18 C17 C16 179.3(4) . . . . ?
C13 C14 C17 C18 1.4(6) . . . . ?
C15 C14 C17 C18 -179.1(4) . . . . ?
C13 C14 C17 C16 -177.5(4) . . . . ?
C15 C14 C17 C16 2.0(5) . . . . ?
C5 C6 C7 C2 0.8(6) . . . . ?
C1 C2 C7 C6 177.7(4) . . . . ?
C3 C2 C7 C6 -1.1(6) . . . . ?
C15 O2 C16 C17 3.1(5) . . . . ?
C18 C17 C16 O2 178.2(4) . . . . ?
C14 C17 C16 O2 -3.1(5) . . . . ?
C5 N2 C8 C9 -83.7(5) . . . . ?
C10 N2 C8 C9 85.4(5) . . . . ?
C5 N2 C10 C11 75.2(5) . . . . ?
C8 N2 C10 C11 -93.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N1 0.82 1.86 2.592(4) 148.0 . yes
C10 H10A O3 0.97 2.58 3.499(6) 158.3 4_556 yes

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_cu_PGIF258
_database_code_depnum_ccdc_archive 'CCDC 1919008'
loop_
_audit_author_name
_audit_author_address
'Kinga Suwinska'
;Cardinal Stefan Wyszynski University in Warsaw
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 N3 O'
_chemical_formula_sum            'C17 H21 N3 O'
_chemical_formula_weight         283.37

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           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                   8.949(5)
_cell_length_b                   21.987(6)
_cell_length_c                   8.156(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.14(4)
_cell_angle_gamma                90
_cell_volume                     1562.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8060
_cell_measurement_theta_min      4.0222
_cell_measurement_theta_max      62.498

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   0.6339
_exptl_transmission_factor_max   0.7522
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.605
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   I\mS
_diffrn_measurement_device_type  'D8 VENTURE DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            27810
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.075
_diffrn_reflns_theta_max         62.583
_diffrn_reflns_theta_full        62.583
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2491
_reflns_number_gt                1796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0749P)²+0.3571P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2491
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45052(19) 0.43983(7) 0.31713(18) 0.0711(5) Uani 1 1 d . . . . .
H1O H 0.510154 0.432981 0.407551 0.107 Uiso 1 1 calc R U . . .
N1 N 0.66539(19) 0.38689(7) 0.53018(19) 0.0539(4) Uani 1 1 d . . . . .
N2 N 0.3243(3) 0.36982(8) -0.2482(2) 0.0782(6) Uani 1 1 d . . . . .
N3 N 0.8305(2) 0.33109(8) 0.7452(2) 0.0615(5) Uani 1 1 d . . . . .
C1 C 0.6753(2) 0.34782(9) 0.4141(2) 0.0514(5) Uani 1 1 d . . . . .
H1 H 0.744349 0.315740 0.440688 0.062 Uiso 1 1 calc R U . . .
C2 C 0.5843(2) 0.35248(8) 0.2478(2) 0.0485(5) Uani 1 1 d . . . . .
C3 C 0.4748(2) 0.39951(9) 0.2014(2) 0.0533(5) Uani 1 1 d . . . . .
C4 C 0.3913(3) 0.40516(9) 0.0392(2) 0.0610(6) Uani 1 1 d . . . . .
H4 H 0.321669 0.437013 0.012249 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4079(2) 0.36418(9) -0.0877(2) 0.0567(5) Uani 1 1 d . . . . .
C6 C 0.5156(2) 0.31638(9) -0.0407(3) 0.0555(5) Uani 1 1 d . . . . .
H6 H 0.529186 0.288064 -0.120805 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5990(2) 0.31161(9) 0.1199(3) 0.0546(5) Uani 1 1 d . . . . .
H7 H 0.669015 0.279875 0.146573 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3341(3) 0.32613(10) -0.3797(3) 0.0674(6) Uani 1 1 d . . . . .
H10A H 0.439661 0.312959 -0.365670 0.081 Uiso 1 1 calc R U . . .
H10B H 0.303077 0.345692 -0.488732 0.081 Uiso 1 1 calc R U . . .
C11 C 0.2338(3) 0.27156(12) -0.3748(3) 0.0842(8) Uani 1 1 d . . . . .
H11A H 0.130304 0.284672 -0.380938 0.126 Uiso 1 1 calc R U . . .
H11B H 0.270838 0.249681 -0.271711 0.126 Uiso 1 1 calc R U . . .
H11C H 0.236113 0.245513 -0.468640 0.126 Uiso 1 1 calc R U . . .
C12 C 0.7546(2) 0.38209(9) 0.6952(2) 0.0515(5) Uani 1 1 d . . . . .
C13 C 0.7566(3) 0.43107(10) 0.8016(3) 0.0696(6) Uani 1 1 d . . . . .
H13 H 0.700779 0.466019 0.763802 0.083 Uiso 1 1 calc R U . . .
C14 C 0.8416(3) 0.42750(11) 0.9632(3) 0.0736(7) Uani 1 1 d . . . . .
H14 H 0.844625 0.460454 1.035316 0.088 Uiso 1 1 calc R U . . .
C15 C 0.9228(2) 0.37567(10) 1.0201(3) 0.0628(6) Uani 1 1 d . . . . .
C16 C 0.9109(3) 0.32953(11) 0.9038(3) 0.0693(6) Uani 1 1 d . . . . .
H16 H 0.964142 0.293841 0.939534 0.083 Uiso 1 1 calc R U . . .
C17 C 1.0157(3) 0.36927(14) 1.1974(3) 0.0915(9) Uani 1 1 d . . . . .
H17A H 1.015793 0.327494 1.231629 0.137 Uiso 1 1 calc R U . . .
H17B H 0.971645 0.394026 1.271122 0.137 Uiso 1 1 calc R U . . .
H17C H 1.119199 0.382194 1.202720 0.137 Uiso 1 1 calc R U . . .
C8A C 0.1869(6) 0.4116(3) -0.2891(5) 0.0655(16) Uani 0.732(15) 1 d . . P A -1
H8AA H 0.106966 0.393562 -0.375946 0.079 Uiso 0.732(15) 1 calc R U P A -1
H8AB H 0.146487 0.417827 -0.189684 0.079 Uiso 0.732(15) 1 calc R U P A -1
C9A C 0.2355(8) 0.4714(4) -0.3491(6) 0.093(2) Uani 0.732(15) 1 d . . P A -1
H9AA H 0.279535 0.464696 -0.444512 0.140 Uiso 0.732(15) 1 calc R U P A -1
H9AB H 0.310153 0.490125 -0.260303 0.140 Uiso 0.732(15) 1 calc R U P A -1
H9AC H 0.147742 0.497520 -0.381039 0.140 Uiso 0.732(15) 1 calc R U P A -1
C8B C 0.2924(17) 0.4349(8) -0.3229(12) 0.070(5) Uani 0.268(15) 1 d . . P A -2
H8BA H 0.350181 0.465531 -0.249286 0.084 Uiso 0.268(15) 1 calc R U P A -2
H8BB H 0.314392 0.438006 -0.433675 0.084 Uiso 0.268(15) 1 calc R U P A -2
C9B C 0.127(2) 0.4392(9) -0.3306(18) 0.083(5) Uani 0.268(15) 1 d . . P A -2
H9BA H 0.091297 0.478913 -0.369521 0.125 Uiso 0.268(15) 1 calc R U P A -2
H9BB H 0.109297 0.432489 -0.220415 0.125 Uiso 0.268(15) 1 calc R U P A -2
H9BC H 0.073820 0.409005 -0.406754 0.125 Uiso 0.268(15) 1 calc R U P A -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.348(2) . ?
O1 H1O 0.8200 . ?
N1 C1 1.296(3) . ?
N1 C12 1.404(3) . ?
N2 C5 1.357(3) . ?
N2 C10 1.457(3) . ?
N2 C8A 1.510(7) . ?
N2 C8B 1.556(18) . ?
N3 C12 1.326(2) . ?
N3 C16 1.330(3) . ?
C1 C2 1.419(3) . ?
C1 H1 0.9300 . ?
C2 C7 1.406(3) . ?
C2 C3 1.415(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.405(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.419(3) . ?
C6 C7 1.356(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C10 C11 1.504(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.381(3) . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 C17 1.502(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8A C9A 1.500(12) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8B C9B 1.47(3) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1O 109.5 . . ?
C1 N1 C12 122.13(17) . . ?
C5 N2 C10 122.50(19) . . ?
C5 N2 C8A 120.7(2) . . ?
C10 N2 C8A 114.9(2) . . ?
C5 N2 C8B 118.3(4) . . ?
C10 N2 C8B 110.8(4) . . ?
C12 N3 C16 116.52(18) . . ?
N1 C1 C2 122.05(19) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C7 C2 C3 116.40(18) . . ?
C7 C2 C1 122.21(18) . . ?
C3 C2 C1 121.38(18) . . ?
O1 C3 C4 118.52(18) . . ?
O1 C3 C2 120.34(17) . . ?
C4 C3 C2 121.14(18) . . ?
C3 C4 C5 121.85(19) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
N2 C5 C4 121.63(19) . . ?
N2 C5 C6 121.32(18) . . ?
C4 C5 C6 117.05(18) . . ?
C7 C6 C5 120.61(18) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 122.92(19) . . ?
C6 C7 H7 118.5 . . ?
C2 C7 H7 118.5 . . ?
N2 C10 C11 111.7(2) . . ?
N2 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 122.28(19) . . ?
N3 C12 N1 119.86(17) . . ?
C13 C12 N1 117.84(18) . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 115.2(2) . . ?
C14 C15 C17 122.5(2) . . ?
C16 C15 C17 122.3(2) . . ?
N3 C16 C15 126.3(2) . . ?
N3 C16 H16 116.9 . . ?
C15 C16 H16 116.9 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9A C8A N2 108.9(5) . . ?
C9A C8A H8AA 109.9 . . ?
N2 C8A H8AA 109.9 . . ?
C9A C8A H8AB 109.9 . . ?
N2 C8A H8AB 109.9 . . ?
H8AA C8A H8AB 108.3 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C9B C8B N2 99.8(14) . . ?
C9B C8B H8BA 111.8 . . ?
N2 C8B H8BA 111.8 . . ?
C9B C8B H8BB 111.8 . . ?
N2 C8B H8BB 111.8 . . ?
H8BA C8B H8BB 109.5 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 179.51(18) . . . . ?
N1 C1 C2 C7 177.44(18) . . . . ?
N1 C1 C2 C3 -1.5(3) . . . . ?
C7 C2 C3 O1 178.36(18) . . . . ?
C1 C2 C3 O1 -2.6(3) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
C1 C2 C3 C4 177.5(2) . . . . ?
O1 C3 C4 C5 -178.7(2) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C10 N2 C5 C4 -176.8(2) . . . . ?
C8A N2 C5 C4 -13.3(4) . . . . ?
C8B N2 C5 C4 38.1(7) . . . . ?
C10 N2 C5 C6 2.9(3) . . . . ?
C8A N2 C5 C6 166.5(3) . . . . ?
C8B N2 C5 C6 -142.1(6) . . . . ?
C3 C4 C5 N2 179.7(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
N2 C5 C6 C7 179.6(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
C1 C2 C7 C6 -178.24(19) . . . . ?
C5 N2 C10 C11 83.0(3) . . . . ?
C8A N2 C10 C11 -81.5(3) . . . . ?
C8B N2 C10 C11 -129.7(6) . . . . ?
C16 N3 C12 C13 -0.7(3) . . . . ?
C16 N3 C12 N1 -179.09(19) . . . . ?
C1 N1 C12 N3 -12.9(3) . . . . ?
C1 N1 C12 C13 168.7(2) . . . . ?
N3 C12 C13 C14 1.2(4) . . . . ?
N1 C12 C13 C14 179.6(2) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 C17 -179.0(2) . . . . ?
C12 N3 C16 C15 -0.1(4) . . . . ?
C14 C15 C16 N3 0.5(4) . . . . ?
C17 C15 C16 N3 179.5(2) . . . . ?
C5 N2 C8A C9A 96.5(3) . . . . ?
C10 N2 C8A C9A -98.8(3) . . . . ?
C5 N2 C8B C9B -109.9(7) . . . . ?
C10 N2 C8B C9B 101.2(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N1 0.82 1.82 2.560(2) 148.7 . yes
C13 H13 O1 0.93 2.48 3.408(3) 176.1 3_666 yes
C8B^b H8BB^b O1 0.97 2.60 3.539(12) 164.0 1_554 yes

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_cu_PGIF170
_database_code_depnum_ccdc_archive 'CCDC 1919006'
loop_
_audit_author_name
_audit_author_address
'Kinga Suwinska'
;Cardinal Stefan Wyszynski University in Warsaw
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36

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      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                   14.488(8)
_cell_length_b                   6.787(2)
_cell_length_c                   16.457(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.99(5)
_cell_angle_gamma                90
_cell_volume                     1598.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1952
_cell_measurement_theta_min      3.0804
_cell_measurement_theta_max      60.7227

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.614
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7709
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   I\mS
_diffrn_measurement_device_type  'D8 VENTURE DUO'
_diffrn_reflns_number            7642
_diffrn_reflns_av_unetI/netI     0.0962
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.443
_diffrn_reflns_theta_max         62.539
_diffrn_reflns_theta_full        62.539
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2471
_reflns_number_gt                1012
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0559P)²+0.2116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2471
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2024(2) 0.7634(4) 0.61712(17) 0.0961(10) Uani 1 1 d . . . . .
H1O H 0.230698 0.732467 0.579618 0.096 Uiso 1 1 calc R U . . .
N1 N 0.30474(19) 0.5445(5) 0.53623(18) 0.0613(9) Uani 1 1 d . . . . .
N2 N 0.1379(2) 0.5370(5) 0.8741(2) 0.0779(10) Uani 1 1 d . . . . .
N3 N 0.5595(3) 0.0298(6) 0.3814(2) 0.1055(15) Uani 1 1 d . . . . .
C1 C 0.3063(2) 0.4182(6) 0.5941(2) 0.0629(11) Uani 1 1 d . . . . .
H1 H 0.339174 0.301617 0.590754 0.075 Uiso 1 1 calc R U . . .
C2 C 0.2603(2) 0.4472(6) 0.6630(2) 0.0559(11) Uani 1 1 d . . . . .
C3 C 0.2105(3) 0.6180(6) 0.6739(2) 0.0603(11) Uani 1 1 d . . . . .
C4 C 0.1692(2) 0.6476(6) 0.7424(2) 0.0680(12) Uani 1 1 d . . . . .
H4 H 0.136601 0.763884 0.747591 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1752(2) 0.5071(6) 0.8041(2) 0.0606(11) Uani 1 1 d . . . . .
C6 C 0.2228(3) 0.3309(6) 0.7930(2) 0.0734(12) Uani 1 1 d . . . . .
H6 H 0.226267 0.231169 0.832098 0.088 Uiso 1 1 calc R U . . .
C7 C 0.2634(3) 0.3077(6) 0.7249(2) 0.0742(13) Uani 1 1 d . . . . .
H7 H 0.295479 0.190985 0.719286 0.089 Uiso 1 1 calc R U . . .
C8 C 0.0841(3) 0.7155(7) 0.8848(2) 0.0915(14) Uani 1 1 d . . . . .
H8A H 0.082527 0.734968 0.942987 0.110 Uiso 1 1 calc R U . . .
H8B H 0.115275 0.828198 0.865114 0.110 Uiso 1 1 calc R U . . .
C9 C -0.0117(3) 0.7057(7) 0.8410(3) 0.1173(18) Uani 1 1 d . . . . .
H9A H -0.010646 0.684865 0.783454 0.176 Uiso 1 1 calc R U . . .
H9B H -0.043304 0.827190 0.848409 0.176 Uiso 1 1 calc R U . . .
H9C H -0.044027 0.598736 0.862351 0.176 Uiso 1 1 calc R U . . .
C10 C 0.1480(3) 0.3957(7) 0.9437(3) 0.0954(15) Uani 1 1 d . . . . .
H10A H 0.208649 0.332476 0.948312 0.114 Uiso 1 1 calc R U . . .
H10B H 0.145825 0.467544 0.994301 0.114 Uiso 1 1 calc R U . . .
C11 C 0.0765(4) 0.2468(7) 0.9343(3) 0.133(2) Uani 1 1 d . . . . .
H11A H 0.016670 0.307533 0.934272 0.199 Uiso 1 1 calc R U . . .
H11B H 0.088436 0.155026 0.979128 0.199 Uiso 1 1 calc R U . . .
H11C H 0.076712 0.178320 0.883293 0.199 Uiso 1 1 calc R U . . .
C12 C 0.3542(2) 0.5118(6) 0.4702(2) 0.0570(11) Uani 1 1 d . . . . .
C13 C 0.3477(3) 0.6558(6) 0.4108(2) 0.0740(12) Uani 1 1 d . . . . .
H13 H 0.310726 0.765830 0.415606 0.089 Uiso 1 1 calc R U . . .
C14 C 0.3945(3) 0.6411(7) 0.3446(2) 0.0814(14) Uani 1 1 d . . . . .
H14 H 0.388695 0.740505 0.305250 0.098 Uiso 1 1 calc R U . . .
C15 C 0.4498(3) 0.4809(8) 0.3363(2) 0.0737(13) Uani 1 1 d . . . . .
H15 H 0.482216 0.471120 0.292005 0.088 Uiso 1 1 calc R U . . .
C16 C 0.4563(3) 0.3350(7) 0.3947(2) 0.0604(11) Uani 1 1 d . . . . .
C17 C 0.4094(3) 0.3482(6) 0.4617(2) 0.0597(11) Uani 1 1 d . . . . .
H17 H 0.414804 0.248020 0.500742 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5140(3) 0.1629(8) 0.3873(2) 0.0743(14) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.352(4) . ?
O1 H1O 0.8200 . ?
N1 C1 1.279(4) . ?
N1 C12 1.410(4) . ?
N2 C5 1.361(4) . ?
N2 C8 1.466(5) . ?
N2 C10 1.484(5) . ?
N3 C18 1.131(5) . ?
C1 C2 1.416(4) . ?
C1 H1 0.9300 . ?
C2 C7 1.386(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.372(4) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(4) . ?
C6 C7 1.355(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.462(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.438(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.374(5) . ?
C12 C17 1.387(4) . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 C18 1.452(6) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1O 109.5 . . ?
C1 N1 C12 121.1(3) . . ?
C5 N2 C8 121.0(3) . . ?
C5 N2 C10 123.5(3) . . ?
C8 N2 C10 115.5(3) . . ?
N1 C1 C2 123.2(4) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C7 C2 C3 115.7(3) . . ?
C7 C2 C1 121.8(4) . . ?
C3 C2 C1 122.5(4) . . ?
O1 C3 C4 117.3(4) . . ?
O1 C3 C2 120.7(4) . . ?
C4 C3 C2 122.0(4) . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N2 C5 C4 121.9(4) . . ?
N2 C5 C6 120.3(4) . . ?
C4 C5 C6 117.8(3) . . ?
C7 C6 C5 119.5(4) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 124.0(4) . . ?
C6 C7 H7 118.0 . . ?
C2 C7 H7 118.0 . . ?
C9 C8 N2 112.6(4) . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
N2 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 112.9(4) . . ?
C11 C10 H10A 109.0 . . ?
N2 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
N2 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.3(4) . . ?
C13 C12 N1 116.7(4) . . ?
C17 C12 N1 125.0(4) . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 118.7(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 C18 119.9(4) . . ?
C17 C16 C18 118.6(4) . . ?
C16 C17 C12 119.6(4) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
N3 C18 C16 179.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 177.9(3) . . . . ?
N1 C1 C2 C7 -179.8(4) . . . . ?
N1 C1 C2 C3 -0.9(6) . . . . ?
C7 C2 C3 O1 -179.6(3) . . . . ?
C1 C2 C3 O1 1.4(5) . . . . ?
C7 C2 C3 C4 1.4(5) . . . . ?
C1 C2 C3 C4 -177.5(3) . . . . ?
O1 C3 C4 C5 -179.2(3) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C8 N2 C5 C4 4.1(6) . . . . ?
C10 N2 C5 C4 -176.0(4) . . . . ?
C8 N2 C5 C6 -176.9(4) . . . . ?
C10 N2 C5 C6 3.0(6) . . . . ?
C3 C4 C5 N2 177.3(4) . . . . ?
C3 C4 C5 C6 -1.7(5) . . . . ?
N2 C5 C6 C7 -176.7(4) . . . . ?
C4 C5 C6 C7 2.4(5) . . . . ?
C5 C6 C7 C2 -1.1(6) . . . . ?
C3 C2 C7 C6 -0.8(6) . . . . ?
C1 C2 C7 C6 178.2(4) . . . . ?
C5 N2 C8 C9 79.0(5) . . . . ?
C10 N2 C8 C9 -100.9(4) . . . . ?
C5 N2 C10 C11 -87.3(5) . . . . ?
C8 N2 C10 C11 92.6(4) . . . . ?
C1 N1 C12 C13 179.6(3) . . . . ?
C1 N1 C12 C17 -1.4(5) . . . . ?
C17 C12 C13 C14 -0.4(5) . . . . ?
N1 C12 C13 C14 178.7(3) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C14 C15 C16 C17 -0.8(6) . . . . ?
C14 C15 C16 C18 179.7(3) . . . . ?
C15 C16 C17 C12 0.2(5) . . . . ?
C18 C16 C17 C12 179.7(3) . . . . ?
C13 C12 C17 C16 0.4(5) . . . . ?
N1 C12 C17 C16 -178.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N1 0.82 1.88 2.607(4) 147.4 . yes
C1 H1 N3 0.93 2.69 3.598(6) 167.0 3_656 yes
C17 H17 N3 0.93 2.69 3.617(6) 176.3 3_656 yes

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_cu_PGIG186
_database_code_depnum_ccdc_archive 'CCDC 1919009'
loop_
_audit_author_name
_audit_author_address
'Kinga Suwinska'
;Cardinal Stefan Wyszynski University in Warsaw
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N4 O'
_chemical_formula_sum            'C19 H18 N4 O'
_chemical_formula_weight         318.37

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      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                   4.875(4)
_cell_length_b                   13.717(17)
_cell_length_c                   14.116(11)
_cell_angle_alpha                112.92(9)
_cell_angle_beta                 96.63(8)
_cell_angle_gamma                92.67(11)
_cell_volume                     859.1(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    274(2)
_cell_measurement_reflns_used    4768
_cell_measurement_theta_min      3.430
_cell_measurement_theta_max      54.5823

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.632
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      274(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   I\mS
_diffrn_measurement_device_type  'D8 VENTURE DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            21603
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.436
_diffrn_reflns_theta_max         59.215
_diffrn_reflns_theta_full        59.215
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2465
_reflns_number_gt                1362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0513P)²+0.2256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2465
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5420(5) 0.36709(18) 0.91835(16) 0.0809(7) Uani 1 1 d . . . . .
H1O H 0.418669 0.399128 0.902788 0.121 Uiso 1 1 calc R U . . .
N1 N 0.2358(5) 0.43574(19) 0.80056(19) 0.0593(7) Uani 1 1 d . . . . .
N2 N 1.0524(6) 0.0746(2) 0.7614(2) 0.0911(9) Uani 1 1 d . . . . .
N3 N -0.6416(7) 0.7961(3) 0.7798(3) 0.1192(13) Uani 1 1 d . . . . .
N4 N -0.3092(8) 0.6251(3) 0.5264(3) 0.1229(13) Uani 1 1 d . . . . .
C1 C 0.3288(6) 0.3665(2) 0.7224(2) 0.0612(8) Uani 1 1 d . . . . .
H1 H 0.265917 0.362198 0.655980 0.073 Uiso 1 1 calc R U . . .
C2 C 0.5230(6) 0.2967(2) 0.7338(2) 0.0544(8) Uani 1 1 d . . . . .
C3 C 0.6221(6) 0.2967(2) 0.8308(2) 0.0582(8) Uani 1 1 d . . . . .
C4 C 0.8012(6) 0.2259(2) 0.8404(3) 0.0695(9) Uani 1 1 d . . . . .
H4 H 0.866223 0.228768 0.906166 0.083 Uiso 1 1 calc R U . . .
C5 C 0.8876(6) 0.1493(2) 0.7531(3) 0.0652(9) Uani 1 1 d . . . . .
C6 C 0.7962(6) 0.1503(2) 0.6554(2) 0.0719(9) Uani 1 1 d . . . . .
H6 H 0.855340 0.102033 0.596103 0.086 Uiso 1 1 calc R U . . .
C7 C 0.6209(6) 0.2222(2) 0.6478(2) 0.0696(9) Uani 1 1 d . . . . .
H7 H 0.563653 0.221725 0.582419 0.084 Uiso 1 1 calc R U . . .
C8A C 1.218(3) 0.0901(8) 0.8613(11) 0.091(5) Uani 0.60(3) 1 d . . P A -1
H8AA H 1.262107 0.165378 0.904098 0.109 Uiso 0.60(3) 1 calc R U P A -1
H8AB H 1.389933 0.057476 0.849631 0.109 Uiso 0.60(3) 1 calc R U P A -1
C9A C 1.049(4) 0.0396(11) 0.9133(16) 0.148(6) Uani 0.60(3) 1 d . . P A -1
H9AA H 0.977804 -0.031152 0.865431 0.222 Uiso 0.60(3) 1 calc R U P A -1
H9AB H 0.896654 0.080637 0.935995 0.222 Uiso 0.60(3) 1 calc R U P A -1
H9AC H 1.161475 0.036477 0.972276 0.222 Uiso 0.60(3) 1 calc R U P A -1
C8B C 1.036(4) 0.0391(12) 0.8562(14) 0.062(5) Uani 0.40(3) 1 d . . P A -2
H8BA H 0.877088 0.065821 0.890581 0.074 Uiso 0.40(3) 1 calc R U P A -2
H8BB H 1.017373 -0.037834 0.831515 0.074 Uiso 0.40(3) 1 calc R U P A -2
C9B C 1.300(5) 0.0856(11) 0.930(2) 0.110(7) Uani 0.40(3) 1 d . . P A -2
H9BA H 1.449709 0.046267 0.900966 0.132 Uiso 0.40(3) 1 calc R U P A -2
H9BB H 1.281674 0.081586 0.995083 0.132 Uiso 0.40(3) 1 calc R U P A -2
H9BC H 1.338271 0.158570 0.940006 0.132 Uiso 0.40(3) 1 calc R U P A -2
C10 C 1.1456(8) -0.0074(3) 0.6710(3) 0.0954(12) Uani 1 1 d . . . . .
H10A H 1.313507 -0.032084 0.694003 0.114 Uiso 1 1 calc R U . . .
H10B H 1.190388 0.024026 0.623136 0.114 Uiso 1 1 calc R U . . .
C11 C 0.9350(9) -0.0990(3) 0.6159(3) 0.1250(15) Uani 1 1 d . . . . .
H11A H 0.775639 -0.076355 0.586343 0.187 Uiso 1 1 calc R U . . .
H11B H 0.880844 -0.127581 0.663874 0.187 Uiso 1 1 calc R U . . .
H11C H 1.011202 -0.152709 0.561443 0.187 Uiso 1 1 calc R U . . .
C12 C 0.0479(6) 0.5053(2) 0.7877(2) 0.0545(7) Uani 1 1 d . . . . .
C13 C -0.0727(6) 0.5636(2) 0.8741(2) 0.0657(9) Uani 1 1 d . . . . .
H13 H -0.029355 0.553252 0.935234 0.079 Uiso 1 1 calc R U . . .
C14 C -0.2537(6) 0.6360(2) 0.8716(2) 0.0710(9) Uani 1 1 d . . . . .
H14 H -0.334016 0.673288 0.930283 0.085 Uiso 1 1 calc R U . . .
C15 C -0.3180(6) 0.6541(2) 0.7821(3) 0.0619(8) Uani 1 1 d . . . . .
C16 C -0.1986(6) 0.5956(2) 0.6949(2) 0.0609(8) Uani 1 1 d . . . . .
C17 C -0.0195(6) 0.5219(2) 0.6977(2) 0.0632(8) Uani 1 1 d . . . . .
H17 H 0.056909 0.482905 0.638503 0.076 Uiso 1 1 calc R U . . .
C18 C -0.4976(7) 0.7336(3) 0.7809(3) 0.0803(10) Uani 1 1 d . . . . .
C19 C -0.2622(7) 0.6118(3) 0.6004(3) 0.0824(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.352(4) . ?
O1 H1O 0.8200 . ?
N1 C1 1.290(4) . ?
N1 C12 1.400(4) . ?
N2 C5 1.363(4) . ?
N2 C10 1.471(4) . ?
N2 C8A 1.474(16) . ?
N2 C8B 1.601(17) . ?
N3 C18 1.138(4) . ?
N4 C19 1.129(4) . ?
C1 C2 1.417(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.371(4) . ?
C4 C5 1.398(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(4) . ?
C6 C7 1.361(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8A C9A 1.48(3) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8B C9B 1.50(4) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C10 C11 1.474(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.382(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(4) . ?
C15 C18 1.433(5) . ?
C16 C17 1.376(4) . ?
C16 C19 1.436(5) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1O 109.5 . . ?
C1 N1 C12 121.6(3) . . ?
C5 N2 C10 122.7(3) . . ?
C5 N2 C8A 121.1(4) . . ?
C10 N2 C8A 113.6(4) . . ?
C5 N2 C8B 118.4(5) . . ?
C10 N2 C8B 113.3(5) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C7 116.5(3) . . ?
C3 C2 C1 122.1(3) . . ?
C7 C2 C1 121.5(3) . . ?
O1 C3 C4 118.0(3) . . ?
O1 C3 C2 120.5(3) . . ?
C4 C3 C2 121.5(3) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N2 C5 C4 121.4(3) . . ?
N2 C5 C6 120.6(3) . . ?
C4 C5 C6 118.0(3) . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 123.0(3) . . ?
C6 C7 H7 118.5 . . ?
C2 C7 H7 118.5 . . ?
N2 C8A C9A 107.2(15) . . ?
N2 C8A H8AA 110.3 . . ?
C9A C8A H8AA 110.3 . . ?
N2 C8A H8AB 110.3 . . ?
C9A C8A H8AB 110.3 . . ?
H8AA C8A H8AB 108.5 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C9B C8B N2 106.4(18) . . ?
C9B C8B H8BA 110.4 . . ?
N2 C8B H8BA 110.4 . . ?
C9B C8B H8BB 110.4 . . ?
N2 C8B H8BB 110.4 . . ?
H8BA C8B H8BB 108.6 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
N2 C10 C11 112.7(3) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.3(3) . . ?
C17 C12 N1 125.4(3) . . ?
C13 C12 N1 116.3(3) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 C18 120.3(3) . . ?
C16 C15 C18 121.2(3) . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 C19 119.2(3) . . ?
C15 C16 C19 120.1(3) . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
N3 C18 C15 179.5(4) . . ?
N4 C19 C16 179.2(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
C12 N1 C1 C2 178.8(2) . . . . ?
N1 C1 C2 C3 1.5(4) . . . . ?
N1 C1 C2 C7 -180.0(3) . . . . ?
C7 C2 C3 O1 179.0(3) . . . . ?
C1 C2 C3 O1 -2.4(4) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C1 C2 C3 C4 177.3(3) . . . . ?
O1 C3 C4 C5 178.5(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C10 N2 C5 C4 179.7(3) . . . . ?
C8A N2 C5 C4 -19.7(8) . . . . ?
C8B N2 C5 C4 27.8(9) . . . . ?
C10 N2 C5 C6 0.6(5) . . . . ?
C8A N2 C5 C6 161.3(7) . . . . ?
C8B N2 C5 C6 -151.3(9) . . . . ?
C3 C4 C5 N2 -176.1(3) . . . . ?
C3 C4 C5 C6 3.0(5) . . . . ?
N2 C5 C6 C7 176.8(3) . . . . ?
C4 C5 C6 C7 -2.3(5) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
C3 C2 C7 C6 2.1(4) . . . . ?
C1 C2 C7 C6 -176.5(3) . . . . ?
C5 N2 C8A C9A 92.8(8) . . . . ?
C10 N2 C8A C9A -104.9(7) . . . . ?
C5 N2 C8B C9B -108.2(8) . . . . ?
C10 N2 C8B C9B 97.3(8) . . . . ?
C5 N2 C10 C11 -82.0(4) . . . . ?
C8A N2 C10 C11 116.0(7) . . . . ?
C8B N2 C10 C11 71.2(9) . . . . ?
C1 N1 C12 C17 -12.2(4) . . . . ?
C1 N1 C12 C13 169.6(3) . . . . ?
C17 C12 C13 C14 0.0(4) . . . . ?
N1 C12 C13 C14 178.3(3) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
C13 C14 C15 C18 -177.1(3) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C18 C15 C16 C17 177.9(3) . . . . ?
C14 C15 C16 C19 179.5(3) . . . . ?
C18 C15 C16 C19 -2.2(5) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C19 C16 C17 C12 179.4(3) . . . . ?
C13 C12 C17 C16 0.9(4) . . . . ?
N1 C12 C17 C16 -177.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N1 0.82 1.85 2.580(4) 146.9 . yes
C1 H1 N4 0.93 2.68 3.549(5) 156.1 2_566 yes
C17 H17 N4 0.93 2.70 3.625(6) 176.5 2_566 yes

_refine_diff_density_max         0.106
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032

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

data_cu_PGIF269
_database_code_depnum_ccdc_archive 'CCDC 1919010'
loop_
_audit_author_name
_audit_author_address
'Kinga Suwinska'
;Cardinal Stefan Wyszynski University in Warsaw
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N4 O'
_chemical_formula_sum            'C15 H18 N4 O'
_chemical_formula_weight         270.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.175(3)
_cell_length_b                   14.950(8)
_cell_length_c                   13.418(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.31(3)
_cell_angle_gamma                90
_cell_volume                     1433.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7580
_cell_measurement_theta_min      4.4399
_cell_measurement_theta_max      58.1072

_exptl_crystal_description       block
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   0.6756
_exptl_transmission_factor_max   0.7518
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   I\mS
_diffrn_measurement_device_type  'D8 VENTURE DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            29516
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.438
_diffrn_reflns_theta_max         60.266
_diffrn_reflns_theta_full        60.266
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2127
_reflns_number_gt                1363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0429P)²+0.7620P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2127
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5690(2) 0.66381(13) 0.52588(15) 0.0609(6) Uani 1 1 d . . . . .
H1O H 0.600341 0.619261 0.558922 0.091 Uiso 1 1 calc R U . . .
N1 N 0.5325(3) 0.52653(14) 0.63516(16) 0.0490(6) Uani 1 1 d . . . . .
N2 N 0.0340(3) 0.81326(18) 0.38049(19) 0.0693(8) Uani 1 1 d . . . . .
N3 N 0.8029(3) 0.46059(15) 0.70066(16) 0.0559(7) Uani 1 1 d . . . . .
N4 N 0.5096(4) 0.40611(17) 0.74579(19) 0.0669(7) Uani 1 1 d . . . . .
C1 C 0.3501(4) 0.53409(18) 0.61555(19) 0.0487(7) Uani 1 1 d . . . . .
H1 H 0.271891 0.492612 0.642227 0.058 Uiso 1 1 calc R U . . .
C2 C 0.2717(3) 0.60316(17) 0.55547(18) 0.0409(6) Uani 1 1 d . . . . .
C3 C 0.3864(3) 0.66734(17) 0.51159(19) 0.0417(7) Uani 1 1 d . . . . .
C4 C 0.3046(3) 0.73574(18) 0.45327(19) 0.0458(7) Uani 1 1 d . . . . .
H4 H 0.381195 0.776598 0.424389 0.055 Uiso 1 1 calc R U . . .
C5 C 0.1122(4) 0.74520(18) 0.4366(2) 0.0470(7) Uani 1 1 d . . . . .
C6 C -0.0027(4) 0.68117(18) 0.4816(2) 0.0482(7) Uani 1 1 d . . . . .
H6 H -0.132390 0.686013 0.472048 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0763(4) 0.61375(18) 0.53779(19) 0.0470(7) Uani 1 1 d . . . . .
H7 H -0.001232 0.572799 0.565859 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1482(4) 0.8800(2) 0.3352(2) 0.0684(9) Uani 1 1 d . . . . .
H8A H 0.074020 0.907461 0.279316 0.082 Uiso 1 1 calc R U . . .
H8B H 0.253318 0.850134 0.308976 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2217(5) 0.9523(2) 0.4066(3) 0.0877(11) Uani 1 1 d . . . . .
H9A H 0.299740 0.992295 0.372962 0.131 Uiso 1 1 calc R U . . .
H9B H 0.293628 0.925671 0.462820 0.131 Uiso 1 1 calc R U . . .
H9C H 0.118648 0.984936 0.429476 0.131 Uiso 1 1 calc R U . . .
C12 C 0.6157(4) 0.46007(18) 0.6974(2) 0.0509(7) Uani 1 1 d . . . . .
C13 C 0.8866(5) 0.3974(2) 0.7582(2) 0.0638(9) Uani 1 1 d . . . . .
H13 H 1.016502 0.394078 0.762945 0.077 Uiso 1 1 calc R U . . .
C14 C 0.7914(5) 0.3372(2) 0.8109(2) 0.0739(10) Uani 1 1 d . . . . .
H14 H 0.853260 0.292922 0.849803 0.089 Uiso 1 1 calc R U . . .
C15 C 0.6013(5) 0.3450(2) 0.8035(2) 0.0801(10) Uani 1 1 d . . . . .
H15 H 0.533013 0.306209 0.840298 0.096 Uiso 1 1 calc R U . . .
C10A C -0.1649(17) 0.8403(7) 0.3825(7) 0.065(4) Uani 0.589(18) 1 d . . P A -1
H10A H -0.177502 0.904855 0.379436 0.078 Uiso 0.589(18) 1 calc R U P A -1
H10B H -0.215117 0.818784 0.442704 0.078 Uiso 0.589(18) 1 calc R U P A -1
C11A C -0.2632(17) 0.7974(6) 0.2910(9) 0.088(3) Uani 0.589(18) 1 d . . P A -1
H11A H -0.204563 0.815719 0.232907 0.131 Uiso 0.589(18) 1 calc R U P A -1
H11B H -0.392150 0.815412 0.284249 0.131 Uiso 0.589(18) 1 calc R U P A -1
H11C H -0.255772 0.733475 0.297526 0.131 Uiso 0.589(18) 1 calc R U P A -1
C10B C -0.173(2) 0.8086(9) 0.3370(14) 0.066(4) Uani 0.411(18) 1 d . . P A -2
H10C H -0.185322 0.825831 0.266973 0.079 Uiso 0.411(18) 1 calc R U P A -2
H10D H -0.221866 0.748589 0.342872 0.079 Uiso 0.411(18) 1 calc R U P A -2
C11B C -0.273(3) 0.8726(9) 0.3976(11) 0.117(5) Uani 0.411(18) 1 d . . P A -2
H11D H -0.264395 0.852742 0.465950 0.140 Uiso 0.411(18) 1 calc R U P A -2
H11E H -0.402011 0.875726 0.371823 0.140 Uiso 0.411(18) 1 calc R U P A -2
H11F H -0.216913 0.930736 0.394412 0.140 Uiso 0.411(18) 1 calc R U P A -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.308(3) . ?
O1 H1O 0.8200 . ?
N1 C1 1.315(3) . ?
N1 C12 1.396(3) . ?
N2 C5 1.356(3) . ?
N2 C8 1.459(4) . ?
N2 C10A 1.485(13) . ?
N2 C10B 1.545(17) . ?
N3 C13 1.328(3) . ?
N3 C12 1.340(4) . ?
N4 C12 1.320(4) . ?
N4 C15 1.331(4) . ?
C1 C2 1.396(4) . ?
C1 H1 0.9300 . ?
C2 C7 1.409(3) . ?
C2 C3 1.426(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.433(4) . ?
C6 C7 1.352(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.507(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C13 C14 1.366(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C10A C11A 1.501(15) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C10B C11B 1.48(2) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1O 109.5 . . ?
C1 N1 C12 122.9(2) . . ?
C5 N2 C8 121.6(2) . . ?
C5 N2 C10A 122.9(4) . . ?
C8 N2 C10A 113.5(4) . . ?
C5 N2 C10B 120.6(5) . . ?
C8 N2 C10B 115.5(5) . . ?
C13 N3 C12 114.4(3) . . ?
C12 N4 C15 115.4(3) . . ?
N1 C1 C2 121.3(3) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C7 121.4(2) . . ?
C1 C2 C3 121.3(2) . . ?
C7 C2 C3 117.2(2) . . ?
O1 C3 C4 118.6(2) . . ?
O1 C3 C2 121.4(2) . . ?
C4 C3 C2 120.0(2) . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
N2 C5 C4 121.4(2) . . ?
N2 C5 C6 120.7(2) . . ?
C4 C5 C6 117.9(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 122.5(3) . . ?
C6 C7 H7 118.8 . . ?
C2 C7 H7 118.8 . . ?
N2 C8 C9 113.8(3) . . ?
N2 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C12 N3 127.6(3) . . ?
N4 C12 N1 119.7(3) . . ?
N3 C12 N1 112.8(3) . . ?
N3 C13 C14 123.3(3) . . ?
N3 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C15 C14 C13 116.8(3) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
N4 C15 C14 122.6(3) . . ?
N4 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
N2 C10A C11A 104.4(9) . . ?
N2 C10A H10A 110.9 . . ?
C11A C10A H10A 110.9 . . ?
N2 C10A H10B 110.9 . . ?
C11A C10A H10B 110.9 . . ?
H10A C10A H10B 108.9 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C11B C10B N2 105.1(15) . . ?
C11B C10B H10C 110.7 . . ?
N2 C10B H10C 110.7 . . ?
C11B C10B H10D 110.7 . . ?
N2 C10B H10D 110.7 . . ?
H10C C10B H10D 108.8 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 177.9(2) . . . . ?
N1 C1 C2 C7 -177.2(2) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
C1 C2 C3 O1 0.1(4) . . . . ?
C7 C2 C3 O1 178.5(2) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C7 C2 C3 C4 -0.9(4) . . . . ?
O1 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C8 N2 C5 C4 -0.2(4) . . . . ?
C10A N2 C5 C4 -163.3(5) . . . . ?
C10B N2 C5 C4 162.1(8) . . . . ?
C8 N2 C5 C6 179.1(3) . . . . ?
C10A N2 C5 C6 16.0(6) . . . . ?
C10B N2 C5 C6 -18.6(9) . . . . ?
C3 C4 C5 N2 179.1(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
N2 C5 C6 C7 -179.7(3) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C2 0.4(4) . . . . ?
C1 C2 C7 C6 178.6(2) . . . . ?
C3 C2 C7 C6 0.2(4) . . . . ?
C5 N2 C8 C9 -80.5(4) . . . . ?
C10A N2 C8 C9 84.1(5) . . . . ?
C10B N2 C8 C9 116.3(8) . . . . ?
C15 N4 C12 N3 -0.6(5) . . . . ?
C15 N4 C12 N1 -179.8(3) . . . . ?
C13 N3 C12 N4 1.5(4) . . . . ?
C13 N3 C12 N1 -179.2(2) . . . . ?
C1 N1 C12 N4 -5.5(4) . . . . ?
C1 N1 C12 N3 175.1(2) . . . . ?
C12 N3 C13 C14 -0.6(4) . . . . ?
N3 C13 C14 C15 -1.1(5) . . . . ?
C12 N4 C15 C14 -1.4(5) . . . . ?
C13 C14 C15 N4 2.1(5) . . . . ?
C5 N2 C10A C11A -99.7(7) . . . . ?
C8 N2 C10A C11A 96.0(7) . . . . ?
C5 N2 C10B C11B 107.0(8) . . . . ?
C8 N2 C10B C11B -89.7(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N1 0.82 1.82 2.550(3) 148.2 . yes
C6 H6 O1 0.93 2.35 3.194(3) 151.2 1_455 yes

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1919007'
loop_
_audit_author_name
_audit_author_address
'Kinga Suwinska'
;Cardinal Stefan Wyszynski University in Warsaw
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N4 O'
_chemical_formula_sum            'C19 H18 N4 O'
_chemical_formula_weight         318.37

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           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                   8.499(6)
_cell_length_b                   8.283(6)
_cell_length_c                   23.92(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.86(3)
_cell_angle_gamma                90
_cell_volume                     1678(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2520
_cell_measurement_theta_min      3.7065
_cell_measurement_theta_max      64.7878

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.648
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   I\mS
_diffrn_measurement_device_type  'D8 VENTURE DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            16345
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.1440
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.710
_diffrn_reflns_theta_max         54.992
_diffrn_reflns_theta_full        54.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2093
_reflns_number_gt                1211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0553P)²+1.5845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2093
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.0868
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2099(5) 0.8273(6) 0.51675(18) 0.0917(15) Uani 1 1 d . . . . .
H1O H 0.277325 0.770415 0.533494 0.137 Uiso 1 1 calc R U . . .
N1 N 0.4857(5) 0.6915(6) 0.5395(2) 0.0614(13) Uani 1 1 d . . . . .
N2 N 0.1172(5) 1.1232(6) 0.34650(19) 0.0659(14) Uani 1 1 d . . . . .
N3 N 0.5353(7) 0.3048(8) 0.7452(3) 0.099(2) Uani 1 1 d . . . . .
N4 N 1.1273(6) 0.3978(7) 0.5758(2) 0.100(2) Uani 1 1 d . . . . .
C1 C 0.5256(6) 0.7547(6) 0.4940(3) 0.0615(16) Uani 1 1 d . . . . .
H1 H 0.627586 0.737848 0.483926 0.074 Uiso 1 1 calc R U . . .
C2 C 0.4189(6) 0.8509(7) 0.4577(2) 0.0562(15) Uani 1 1 d . . . . .
C3 C 0.2650(7) 0.8843(7) 0.4694(2) 0.0622(16) Uani 1 1 d . . . . .
C4 C 0.1641(7) 0.9759(7) 0.4332(2) 0.0675(16) Uani 1 1 d . . . . .
H4 H 0.062373 0.998377 0.442576 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2141(6) 1.0342(7) 0.3832(2) 0.0540(14) Uani 1 1 d . . . . .
C6 C 0.3708(6) 1.0010(6) 0.3713(2) 0.0590(15) Uani 1 1 d . . . . .
H6 H 0.408131 1.039225 0.338331 0.071 Uiso 1 1 calc R U . . .
C7 C 0.4681(6) 0.9120(6) 0.4085(2) 0.0585(15) Uani 1 1 d . . . . .
H7 H 0.571203 0.892253 0.400025 0.070 Uiso 1 1 calc R U . . .
C8 C -0.0454(8) 1.1558(9) 0.3569(3) 0.094(2) Uani 1 1 d . . . . .
H8A H -0.080889 1.251296 0.336001 0.113 Uiso 1 1 calc R U . . .
H8AB H -0.050041 1.179131 0.396474 0.113 Uiso 1 1 calc R U . . .
C9 C -0.1538(8) 1.0219(11) 0.3412(3) 0.134(3) Uani 1 1 d . . . . .
H9A H -0.154094 1.001455 0.301695 0.201 Uiso 1 1 calc R U . . .
H9B H -0.258521 1.050058 0.349985 0.201 Uiso 1 1 calc R U . . .
H9C H -0.119721 0.926742 0.361710 0.201 Uiso 1 1 calc R U . . .
C10 C 0.1670(7) 1.1782(7) 0.2930(2) 0.0673(17) Uani 1 1 d . . . . .
H10A H 0.275065 1.216282 0.298741 0.081 Uiso 1 1 calc R U . . .
H10B H 0.101587 1.269070 0.280154 0.081 Uiso 1 1 calc R U . . .
C11 C 0.1574(7) 1.0496(8) 0.2474(3) 0.087(2) Uani 1 1 d . . . . .
H11A H 0.051731 1.007995 0.242334 0.130 Uiso 1 1 calc R U . . .
H11B H 0.229206 0.963446 0.258136 0.130 Uiso 1 1 calc R U . . .
H11C H 0.185249 1.096317 0.212807 0.130 Uiso 1 1 calc R U . . .
C12 C 0.5946(6) 0.5961(6) 0.5735(2) 0.0561(15) Uani 1 1 d . . . . .
C13 C 0.5409(7) 0.5338(7) 0.6217(2) 0.0650(16) Uani 1 1 d . . . . .
H13 H 0.439511 0.558616 0.630817 0.078 Uiso 1 1 calc R U . . .
C14 C 0.6364(6) 0.4338(7) 0.6568(2) 0.0591(15) Uani 1 1 d . . . . .
C15 C 0.7895(6) 0.3975(7) 0.6449(2) 0.0626(16) Uani 1 1 d . . . . .
H15 H 0.854068 0.331447 0.668436 0.075 Uiso 1 1 calc R U . . .
C16 C 0.8425(6) 0.4632(7) 0.5967(3) 0.0598(15) Uani 1 1 d . . . . .
C17 C 0.7482(6) 0.5632(7) 0.5616(2) 0.0620(15) Uani 1 1 d . . . . .
H17 H 0.787876 0.608047 0.530012 0.074 Uiso 1 1 calc R U . . .
C18 C 0.5776(7) 0.3638(8) 0.7060(3) 0.0728(18) Uani 1 1 d . . . . .
C19 C 1.0003(7) 0.4254(8) 0.5841(3) 0.0759(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.346(6) . ?
O1 H1O 0.8200 . ?
N1 C1 1.279(7) . ?
N1 C12 1.420(6) . ?
N2 C5 1.368(6) . ?
N2 C8 1.450(7) . ?
N2 C10 1.454(7) . ?
N3 C18 1.140(7) . ?
N4 C19 1.138(6) . ?
C1 C2 1.441(7) . ?
C1 H1 0.9300 . ?
C2 C7 1.379(7) . ?
C2 C3 1.389(7) . ?
C3 C4 1.391(7) . ?
C4 C5 1.390(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(7) . ?
C6 C7 1.376(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.470(10) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.523(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.374(7) . ?
C12 C17 1.388(7) . ?
C13 C14 1.391(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(7) . ?
C14 C18 1.440(8) . ?
C15 C16 1.384(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(7) . ?
C16 C19 1.434(8) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1O 109.5 . . ?
C1 N1 C12 120.6(5) . . ?
C5 N2 C8 121.4(5) . . ?
C5 N2 C10 122.0(5) . . ?
C8 N2 C10 116.4(5) . . ?
N1 C1 C2 122.7(5) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C7 C2 C3 117.3(5) . . ?
C7 C2 C1 119.8(5) . . ?
C3 C2 C1 122.9(5) . . ?
O1 C3 C2 120.1(5) . . ?
O1 C3 C4 118.3(5) . . ?
C2 C3 C4 121.6(5) . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N2 C5 C4 121.9(5) . . ?
N2 C5 C6 120.2(5) . . ?
C4 C5 C6 117.9(5) . . ?
C7 C6 C5 120.0(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 122.6(5) . . ?
C6 C7 H7 118.7 . . ?
C2 C7 H7 118.7 . . ?
N2 C8 C9 113.7(6) . . ?
N2 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N2 C8 H8AB 108.8 . . ?
C9 C8 H8AB 108.8 . . ?
H8A C8 H8AB 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 114.2(5) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.9(6) . . ?
C13 C12 N1 116.3(5) . . ?
C17 C12 N1 124.8(5) . . ?
C12 C13 C14 120.8(6) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 120.9(6) . . ?
C15 C14 C18 118.5(6) . . ?
C13 C14 C18 120.6(5) . . ?
C16 C15 C14 117.5(6) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C17 121.9(5) . . ?
C15 C16 C19 117.7(6) . . ?
C17 C16 C19 120.4(6) . . ?
C16 C17 C12 119.9(5) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
N3 C18 C14 177.7(7) . . ?
N4 C19 C16 177.7(8) . . ?

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
C12 N1 C1 C2 179.3(5) . . . . ?
N1 C1 C2 C7 -178.3(5) . . . . ?
N1 C1 C2 C3 0.7(8) . . . . ?
C7 C2 C3 O1 179.7(5) . . . . ?
C1 C2 C3 O1 0.7(9) . . . . ?
C7 C2 C3 C4 -0.2(8) . . . . ?
C1 C2 C3 C4 -179.2(5) . . . . ?
O1 C3 C4 C5 -178.5(5) . . . . ?
C2 C3 C4 C5 1.4(9) . . . . ?
C8 N2 C5 C4 -2.5(9) . . . . ?
C10 N2 C5 C4 -177.3(5) . . . . ?
C8 N2 C5 C6 178.4(5) . . . . ?
C10 N2 C5 C6 3.7(8) . . . . ?
C3 C4 C5 N2 179.3(5) . . . . ?
C3 C4 C5 C6 -1.6(8) . . . . ?
N2 C5 C6 C7 179.7(5) . . . . ?
C4 C5 C6 C7 0.6(8) . . . . ?
C5 C6 C7 C2 0.6(8) . . . . ?
C3 C2 C7 C6 -0.8(8) . . . . ?
C1 C2 C7 C6 178.2(5) . . . . ?
C5 N2 C8 C9 -81.1(8) . . . . ?
C10 N2 C8 C9 93.9(7) . . . . ?
C5 N2 C10 C11 79.5(7) . . . . ?
C8 N2 C10 C11 -95.5(6) . . . . ?
C1 N1 C12 C13 179.9(5) . . . . ?
C1 N1 C12 C17 0.0(8) . . . . ?
C17 C12 C13 C14 -2.5(8) . . . . ?
N1 C12 C13 C14 177.6(5) . . . . ?
C12 C13 C14 C15 1.5(8) . . . . ?
C12 C13 C14 C18 -177.6(6) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C18 C14 C15 C16 178.6(5) . . . . ?
C14 C15 C16 C17 0.7(8) . . . . ?
C14 C15 C16 C19 -179.7(5) . . . . ?
C15 C16 C17 C12 -1.8(8) . . . . ?
C19 C16 C17 C12 178.6(5) . . . . ?
C13 C12 C17 C16 2.6(8) . . . . ?
N1 C12 C17 C16 -177.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N1 0.82 1.88 2.616(6) 148.4 . yes
C8 H8AB O1 0.97 2.58 3.438(8) 148.2 3_576 yes
C10 H10A N3 0.97 2.65 3.426(8) 136.8 4_575 yes
C17 H17 N4 0.93 2.69 3.550(8) 154.3 3_766 yes

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041


# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Poor crystal quality, weakly diffracting crystal
;
# end Validation Reply Form

