 
data_A25169O_014
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C19 H13 N5, C2 H4 O2'
_chemical_formula_sum
 'C21 H17 N5 O2' 
_chemical_formula_weight          371.40

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    17.5287(5)
_cell_length_b                    4.8349(2)
_cell_length_c                    20.6487(6)
_cell_angle_alpha                 90
_cell_angle_beta                  91.2351(14)
_cell_angle_gamma                 90
_cell_volume                      1749.56(10)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     8690
_cell_measurement_theta_min       3.02
_cell_measurement_theta_max       26.00
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.410          
_exptl_crystal_F_000              776
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.188
_exptl_crystal_size_mid           0.026
_exptl_crystal_size_min           0.023
_exptl_absorpt_coefficient_mu     0.095
_shelx_estimated_absorpt_T_min    0.982
_shelx_estimated_absorpt_T_max    0.998
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.6773
_exptl_absorpt_correction_T_max   0.7453
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Ius 3.0 microfocus source'
_diffrn_measurement_device_type   'PHOTON II CPAD detector'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             16918
_diffrn_reflns_av_unetI/netI      0.0567
_diffrn_reflns_av_R_equivalents   0.0935
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -5
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          3.017
_diffrn_reflns_theta_max          26.017
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.994
_diffrn_measured_fraction_theta_full  0.995
_diffrn_reflns_Laue_measured_fraction_max    0.994
_diffrn_reflns_Laue_measured_fraction_full   0.995
_diffrn_reflns_point_group_measured_fraction_max   0.994
_diffrn_reflns_point_group_measured_fraction_full  0.995
_reflns_number_total              3402
_reflns_number_gt                 2383
_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 APEX5 software' 
_computing_cell_refinement        'Bruker APEX5 software' 
_computing_data_reduction         'Bruker APEX5 software' 
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.0382P)²+0.8470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3402
_refine_ls_number_parameters      260
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0891
_refine_ls_R_factor_gt            0.0512
_refine_ls_wR_factor_ref          0.1198
_refine_ls_wR_factor_gt           0.1048
_refine_ls_goodness_of_fit_ref    1.069
_refine_ls_restrained_S_all       1.069
_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
C1 C 0.70839(11) 0.7171(5) 0.29256(8) 0.0237(4) Uani 1 1 d . . . . .
N2 N 0.64371(9) 0.5986(4) 0.27824(7) 0.0273(4) Uani 1 1 d . . . . .
C3 C 0.61585(11) 0.4115(5) 0.32298(9) 0.0262(4) Uani 1 1 d . . . . .
C4 C 0.54499(12) 0.2874(5) 0.31179(9) 0.0320(5) Uani 1 1 d . . . . .
H4 H 0.515662 0.335244 0.274220 0.038 Uiso 1 1 calc R U . . .
C5 C 0.51713(12) 0.0964(5) 0.35464(10) 0.0359(5) Uani 1 1 d . . . . .
H5 H 0.468563 0.014404 0.346727 0.043 Uiso 1 1 calc R U . . .
C6 C 0.56017(13) 0.0224(5) 0.40989(10) 0.0354(5) Uani 1 1 d . . . . .
H6 H 0.541259 -0.112370 0.438926 0.042 Uiso 1 1 calc R U . . .
C7 C 0.63009(12) 0.1453(5) 0.42215(9) 0.0324(5) Uani 1 1 d . . . . .
H7 H 0.659186 0.095287 0.459691 0.039 Uiso 1 1 calc R U . . .
C8 C 0.65812(11) 0.3429(5) 0.37951(9) 0.0255(4) Uani 1 1 d . . . . .
N9 N 0.72710(9) 0.4723(4) 0.39345(7) 0.0259(4) Uani 1 1 d . . . . .
C10 C 0.75058(11) 0.6606(5) 0.35283(8) 0.0248(4) Uani 1 1 d . . . . .
N11 N 0.81540(10) 0.8000(4) 0.36620(8) 0.0289(4) Uani 1 1 d . . . . .
H11 H 0.8382(14) 0.758(6) 0.4023(12) 0.043 Uiso 1 1 d . U . . .
C12 C 0.84526(11) 0.9970(5) 0.32474(9) 0.0268(5) Uani 1 1 d . . . . .
C13 C 0.91102(11) 1.1429(5) 0.34154(9) 0.0305(5) Uani 1 1 d . . . . .
H13 H 0.936882 1.105707 0.381498 0.037 Uiso 1 1 calc R U . . .
C14 C 0.93906(12) 1.3431(5) 0.30008(10) 0.0337(5) Uani 1 1 d . . . . .
H14 H 0.984236 1.442035 0.311405 0.040 Uiso 1 1 calc R U . . .
C15 C 0.90085(12) 1.3974(5) 0.24231(10) 0.0341(5) Uani 1 1 d . . . . .
H15 H 0.919577 1.535825 0.214128 0.041 Uiso 1 1 calc R U . . .
C16 C 0.83550(12) 1.2520(5) 0.22509(9) 0.0295(5) Uani 1 1 d . . . . .
H16 H 0.809524 1.291890 0.185331 0.035 Uiso 1 1 calc R U . . .
C17 C 0.80771(11) 1.0481(5) 0.26562(9) 0.0263(5) Uani 1 1 d . . . . .
N18 N 0.74098(9) 0.8983(4) 0.24946(7) 0.0276(4) Uani 1 1 d . . . . .
C19 C 0.71227(11) 0.9014(5) 0.18306(8) 0.0263(4) Uani 1 1 d . . . . .
C20 C 0.65073(13) 1.0573(6) 0.16561(10) 0.0443(7) Uani 1 1 d . . . . .
H20 H 0.624961 1.166512 0.196504 0.053 Uiso 1 1 calc R U . . .
C21 C 0.62681(14) 1.0516(7) 0.10122(11) 0.0490(7) Uani 1 1 d . . . . .
H21 H 0.583888 1.157184 0.087061 0.059 Uiso 1 1 calc R U . . .
C22 C 0.66572(13) 0.8922(5) 0.05827(9) 0.0343(5) Uani 1 1 d . . . . .
H22 H 0.650027 0.882809 0.014000 0.041 Uiso 1 1 calc R U . . .
C23 C 0.72773(15) 0.7467(6) 0.08066(10) 0.0445(6) Uani 1 1 d . . . . .
H23 H 0.755053 0.637762 0.050687 0.053 Uiso 1 1 calc R U . . .
N24 N 0.75201(12) 0.7496(5) 0.14254(8) 0.0431(5) Uani 1 1 d . . . . .
O25 O 0.81425(8) 0.2470(4) 0.48728(7) 0.0372(4) Uani 1 1 d . . . . .
H25 H 0.7825(16) 0.341(7) 0.4535(13) 0.056 Uiso 1 1 d . U . . .
O26 O 0.89260(9) 0.6071(4) 0.48031(8) 0.0426(4) Uani 1 1 d . . . . .
C27 C 0.87487(12) 0.3896(5) 0.50510(9) 0.0326(5) Uani 1 1 d . . . . .
C28 C 0.92042(14) 0.2577(7) 0.55886(11) 0.0507(7) Uani 1 1 d . . . . .
H28A H 0.974407 0.305597 0.554590 0.076 Uiso 1 1 calc R U . . .
H28B H 0.914424 0.056376 0.556625 0.076 Uiso 1 1 calc R U . . .
H28C H 0.902279 0.324712 0.600592 0.076 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
C1 N2 1.299(3) . ?
C1 N18 1.381(3) . ?
C1 C10 1.460(3) . ?
N2 C3 1.389(3) . ?
C3 C4 1.394(3) . ?
C3 C8 1.409(3) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(3) . ?
C7 H7 0.9500 . ?
C8 N9 1.386(3) . ?
N9 C10 1.310(3) . ?
C10 N11 1.345(3) . ?
N11 C12 1.390(3) . ?
N11 H11 0.86(3) . ?
C12 C13 1.389(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 N18 1.409(3) . ?
N18 C19 1.450(2) . ?
C19 N24 1.322(3) . ?
C19 C20 1.358(3) . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.368(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.367(3) . ?
C22 H22 0.9500 . ?
C23 N24 1.338(3) . ?
C23 H23 0.9500 . ?
O25 C27 1.313(3) . ?
O25 H25 0.99(3) . ?
O26 C27 1.213(3) . ?
C27 C28 1.496(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
 
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
N2 C1 N18 120.29(17) . . ?
N2 C1 C10 122.37(18) . . ?
N18 C1 C10 117.32(17) . . ?
C1 N2 C3 116.97(16) . . ?
N2 C3 C4 119.65(17) . . ?
N2 C3 C8 121.21(18) . . ?
C4 C3 C8 119.1(2) . . ?
C5 C4 C3 120.64(19) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.15(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N9 C8 C7 119.70(17) . . ?
N9 C8 C3 120.44(19) . . ?
C7 C8 C3 119.86(19) . . ?
C10 N9 C8 117.73(16) . . ?
N9 C10 N11 119.50(17) . . ?
N9 C10 C1 121.03(18) . . ?
N11 C10 C1 119.45(18) . . ?
C10 N11 C12 122.99(17) . . ?
C10 N11 H11 115.7(19) . . ?
C12 N11 H11 121.3(19) . . ?
C13 C12 N11 121.03(18) . . ?
C13 C12 C17 120.1(2) . . ?
N11 C12 C17 118.86(19) . . ?
C12 C13 C14 120.18(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 120.34(19) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 119.18(19) . . ?
C16 C17 N18 121.48(17) . . ?
C12 C17 N18 119.30(19) . . ?
C1 N18 C17 121.72(16) . . ?
C1 N18 C19 118.39(17) . . ?
C17 N18 C19 119.21(16) . . ?
N24 C19 C20 124.48(18) . . ?
N24 C19 N18 114.57(18) . . ?
C20 C19 N18 120.92(19) . . ?
C19 C20 C21 117.8(2) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
C22 C21 C20 119.2(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C23 C22 C21 118.34(19) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
N24 C23 C22 123.5(2) . . ?
N24 C23 H23 118.3 . . ?
C22 C23 H23 118.3 . . ?
C19 N24 C23 116.7(2) . . ?
C27 O25 H25 113.3(18) . . ?
O26 C27 O25 123.38(19) . . ?
O26 C27 C28 123.0(2) . . ?
O25 C27 C28 113.6(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
N18 C1 N2 C3 177.78(19) . . . . ?
C10 C1 N2 C3 -0.4(3) . . . . ?
C1 N2 C3 C4 177.0(2) . . . . ?
C1 N2 C3 C8 -3.4(3) . . . . ?
N2 C3 C4 C5 178.4(2) . . . . ?
C8 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 N9 177.7(2) . . . . ?
C6 C7 C8 C3 -1.7(3) . . . . ?
N2 C3 C8 N9 3.4(3) . . . . ?
C4 C3 C8 N9 -177.0(2) . . . . ?
N2 C3 C8 C7 -177.2(2) . . . . ?
C4 C3 C8 C7 2.4(3) . . . . ?
C7 C8 N9 C10 -178.6(2) . . . . ?
C3 C8 N9 C10 0.7(3) . . . . ?
C8 N9 C10 N11 176.89(19) . . . . ?
C8 N9 C10 C1 -4.5(3) . . . . ?
N2 C1 C10 N9 4.6(3) . . . . ?
N18 C1 C10 N9 -173.64(19) . . . . ?
N2 C1 C10 N11 -176.8(2) . . . . ?
N18 C1 C10 N11 5.0(3) . . . . ?
N9 C10 N11 C12 178.09(19) . . . . ?
C1 C10 N11 C12 -0.5(3) . . . . ?
C10 N11 C12 C13 177.8(2) . . . . ?
C10 N11 C12 C17 -1.8(3) . . . . ?
N11 C12 C13 C14 -178.6(2) . . . . ?
C17 C12 C13 C14 1.0(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C12 1.8(3) . . . . ?
C15 C16 C17 N18 179.5(2) . . . . ?
C13 C12 C17 C16 -2.1(3) . . . . ?
N11 C12 C17 C16 177.5(2) . . . . ?
C13 C12 C17 N18 -179.9(2) . . . . ?
N11 C12 C17 N18 -0.3(3) . . . . ?
N2 C1 N18 C17 174.6(2) . . . . ?
C10 C1 N18 C17 -7.2(3) . . . . ?
N2 C1 N18 C19 -14.9(3) . . . . ?
C10 C1 N18 C19 163.34(18) . . . . ?
C16 C17 N18 C1 -172.8(2) . . . . ?
C12 C17 N18 C1 4.9(3) . . . . ?
C16 C17 N18 C19 16.8(3) . . . . ?
C12 C17 N18 C19 -165.47(19) . . . . ?
C1 N18 C19 N24 -96.4(2) . . . . ?
C17 N18 C19 N24 74.4(3) . . . . ?
C1 N18 C19 C20 85.6(3) . . . . ?
C17 N18 C19 C20 -103.7(3) . . . . ?
N24 C19 C20 C21 1.7(4) . . . . ?
N18 C19 C20 C21 179.5(2) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C22 C23 N24 0.7(5) . . . . ?
C20 C19 N24 C23 -1.8(4) . . . . ?
N18 C19 N24 C23 -179.8(2) . . . . ?
C22 C23 N24 C19 0.6(4) . . . . ?
 
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
N11 H11 O26  0.86(3) 1.99(3) 2.849(2) 172(3) . yes
O25 H25 N9  0.99(3) 1.68(3) 2.673(2) 175(3) . yes
 
_refine_diff_density_max    0.208
_refine_diff_density_min   -0.243
_refine_diff_density_rms    0.046



