#------------------------------------------------------------------------------
#$Date: 2021-04-10 08:01:47 +0300 (Sat, 10 Apr 2021) $
#$Revision: 264030 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243797.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243797
loop_
_publ_author_name
'Naghiyev, Farid N.'
'Tereshina, Tatiana A.'
'Khrustalev, Victor N.'
'Akkurt, Mehmet'
'Khalilov, Ali N.'
'Akobirshoeva, Anzurat A.'
'Mamedov, İbrahim G.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 6-amino-8-phenyl-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbonitrile
;
_journal_coeditor_code           HB7972
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              512
_journal_page_last               515
_journal_paper_doi               10.1107/S2056989021003625
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C16 H15 N5'
_chemical_formula_moiety         'C16 H15 N5'
_chemical_formula_sum            'C16 H15 N5'
_chemical_formula_weight         277.33
_chemical_name_systematic
;
6-Amino-8-phenyl-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine-\
7,9-dicarbonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.070(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2521(6)
_cell_length_b                   10.2774(8)
_cell_length_c                   16.2102(12)
_cell_measurement_reflns_used    1452
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.35
_cell_volume                     1373.89(18)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21387
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         2.347
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.267
_refine_ls_extinction_coef       0.00309(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1614
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0647P)²+0.4109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                1519
_reflns_number_total             3146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7972sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243797
_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.
;
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           .2013
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.6921(3) 0.5239(3) 0.56852(16) 0.0325(7) Uani d 1 . .
H H1 0.787(4) 0.541(3) 0.549(2) 0.039 Uiso d 1 . .
C C2 0.6082(4) 0.6387(3) 0.5990(2) 0.0376(8) Uani d 1 . .
H H2A 0.5337 0.6740 0.5553 0.045 Uiso calc 1 . .
H H2B 0.6879 0.7071 0.6148 0.045 Uiso calc 1 . .
C C3 0.5135(4) 0.5990(3) 0.6733(2) 0.0401(9) Uani d 1 . .
H H3A 0.5893 0.5737 0.7193 0.048 Uiso calc 1 . .
H H3B 0.4474 0.6731 0.6918 0.048 Uiso calc 1 . .
C C4 0.4049(4) 0.4861(3) 0.6502(2) 0.0376(8) Uani d 1 . .
H H4A 0.3478 0.4564 0.6995 0.045 Uiso calc 1 . .
H H4B 0.3224 0.5144 0.6082 0.045 Uiso calc 1 . .
N N5 0.5002(3) 0.3771(2) 0.61711(15) 0.0317(6) Uani d 1 . .
C C6 0.4428(4) 0.2509(3) 0.62264(19) 0.0321(8) Uani d 1 . .
N N6 0.2881(3) 0.2398(3) 0.65141(19) 0.0388(7) Uani d 1 . .
H H6A 0.211(4) 0.313(4) 0.650(2) 0.047 Uiso d 1 . .
H H6B 0.255(4) 0.155(4) 0.645(2) 0.047 Uiso d 1 . .
C C7 0.5356(4) 0.1470(3) 0.60400(19) 0.0306(7) Uani d 1 . .
C C8 0.7070(4) 0.1551(3) 0.57515(18) 0.0298(7) Uani d 1 . .
H H8 0.7106 0.1095 0.5208 0.036 Uiso calc 1 . .
C C9 0.7468(4) 0.2969(3) 0.56112(19) 0.0315(8) Uani d 1 . .
C C9A 0.6496(4) 0.3993(3) 0.58218(18) 0.0309(7) Uani d 1 . .
C C10 0.4710(4) 0.0202(3) 0.6141(2) 0.0340(8) Uani d 1 . .
N N10 0.4207(3) -0.0837(3) 0.62453(19) 0.0443(8) Uani d 1 . .
C C11 0.8298(4) 0.0898(3) 0.63415(19) 0.0297(7) Uani d 1 . .
C C12 0.9153(4) -0.0185(3) 0.6105(2) 0.0363(8) Uani d 1 . .
H H12 0.8957 -0.0541 0.5570 0.044 Uiso calc 1 . .
C C13 1.0300(4) -0.0762(3) 0.6639(2) 0.0421(9) Uani d 1 . .
H H13 1.0905 -0.1492 0.6465 0.051 Uiso calc 1 . .
C C14 1.0550(4) -0.0269(3) 0.7422(2) 0.0431(9) Uani d 1 . .
H H14 1.1318 -0.0671 0.7791 0.052 Uiso calc 1 . .
C C15 0.9700(4) 0.0802(3) 0.7676(2) 0.0402(9) Uani d 1 . .
H H15 0.9878 0.1139 0.8218 0.048 Uiso calc 1 . .
C C16 0.8582(4) 0.1383(3) 0.7135(2) 0.0355(8) Uani d 1 . .
H H16 0.7998 0.2125 0.7309 0.043 Uiso calc 1 . .
C C17 0.8973(4) 0.3241(3) 0.5286(2) 0.0360(8) Uani d 1 . .
N N17 1.0252(4) 0.3441(3) 0.5036(2) 0.0497(8) Uani d 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9A N1 C2 . . 125.6(3) ?
C9A N1 H1 . . 119(2) ?
C2 N1 H1 . . 114(2) ?
N1 C2 C3 . . 108.4(3) ?
N1 C2 H2A . . 110.0 ?
C3 C2 H2A . . 110.0 ?
N1 C2 H2B . . 110.0 ?
C3 C2 H2B . . 110.0 ?
H2A C2 H2B . . 108.4 ?
C4 C3 C2 . . 109.2(3) ?
C4 C3 H3A . . 109.8 ?
C2 C3 H3A . . 109.8 ?
C4 C3 H3B . . 109.8 ?
C2 C3 H3B . . 109.8 ?
H3A C3 H3B . . 108.3 ?
N5 C4 C3 . . 110.8(3) ?
N5 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
N5 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
C6 N5 C9A . . 119.3(3) ?
C6 N5 C4 . . 119.9(3) ?
C9A N5 C4 . . 120.8(3) ?
C7 C6 N6 . . 123.2(3) ?
C7 C6 N5 . . 121.8(3) ?
N6 C6 N5 . . 115.0(3) ?
C6 N6 H6A . . 122(2) ?
C6 N6 H6B . . 109(2) ?
H6A N6 H6B . . 122(3) ?
C6 C7 C10 . . 118.7(3) ?
C6 C7 C8 . . 124.7(3) ?
C10 C7 C8 . . 116.6(3) ?
C7 C8 C9 . . 108.2(3) ?
C7 C8 C11 . . 113.0(2) ?
C9 C8 C11 . . 112.1(2) ?
C7 C8 H8 . . 107.8 ?
C9 C8 H8 . . 107.8 ?
C11 C8 H8 . . 107.8 ?
C9A C9 C17 . . 118.5(3) ?
C9A C9 C8 . . 124.6(3) ?
C17 C9 C8 . . 116.8(3) ?
N1 C9A C9 . . 122.0(3) ?
N1 C9A N5 . . 117.4(3) ?
C9 C9A N5 . . 120.6(3) ?
N10 C10 C7 . . 178.0(3) ?
C12 C11 C16 . . 118.4(3) ?
C12 C11 C8 . . 121.1(3) ?
C16 C11 C8 . . 120.5(3) ?
C11 C12 C13 . . 120.9(3) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C14 C13 C12 . . 119.6(3) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C13 C14 C15 . . 120.7(3) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C14 C15 C16 . . 119.4(3) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C15 C16 C11 . . 121.1(3) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
N17 C17 C9 . . 177.7(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C9A . 1.349(4) ?
N1 C2 . 1.463(4) ?
N1 H1 . 0.87(3) ?
C2 C3 . 1.515(5) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.505(4) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 N5 . 1.481(4) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
N5 C6 . 1.384(4) ?
N5 C9A . 1.394(4) ?
C6 C7 . 1.355(4) ?
C6 N6 . 1.379(4) ?
N6 H6A . 0.99(4) ?
N6 H6B . 0.92(4) ?
C7 C10 . 1.420(5) ?
C7 C8 . 1.508(4) ?
C8 C9 . 1.513(4) ?
C8 C11 . 1.524(4) ?
C8 H8 . 1.0000 ?
C9 C9A . 1.373(4) ?
C9 C17 . 1.395(5) ?
C10 N10 . 1.160(4) ?
C11 C12 . 1.379(4) ?
C11 C16 . 1.392(4) ?
C12 C13 . 1.393(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.375(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.376(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.385(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 N17 . 1.162(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N17 3_766 0.87(3) 2.15(3) 2.975(4) 157(3) yes
C8 H8 N10 3_656 1.00 2.57 3.447(4) 146 yes
C2 H2A Cg2 3_666 0.99 2.67 3.620(3) 161 yes
N6 H6B Cg3 1_455 0.92(4) 2.98(3) 3.633(3) 129(3) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9A N1 C2 C3 . . . . 22.3(4) ?
N1 C2 C3 C4 . . . . -54.1(3) ?
C2 C3 C4 N5 . . . . 55.8(4) ?
C3 C4 N5 C6 . . . . 154.4(3) ?
C3 C4 N5 C9A . . . . -23.9(4) ?
C9A N5 C6 C7 . . . . 7.8(4) ?
C4 N5 C6 C7 . . . . -170.5(3) ?
C9A N5 C6 N6 . . . . -174.6(3) ?
C4 N5 C6 N6 . . . . 7.1(4) ?
N6 C6 C7 C10 . . . . 0.3(5) ?
N5 C6 C7 C10 . . . . 177.6(3) ?
N6 C6 C7 C8 . . . . -177.9(3) ?
N5 C6 C7 C8 . . . . -0.5(5) ?
C6 C7 C8 C9 . . . . -6.8(4) ?
C10 C7 C8 C9 . . . . 175.0(3) ?
C6 C7 C8 C11 . . . . 117.8(3) ?
C10 C7 C8 C11 . . . . -60.3(4) ?
C7 C8 C9 C9A . . . . 8.0(4) ?
C11 C8 C9 C9A . . . . -117.3(3) ?
C7 C8 C9 C17 . . . . -175.7(3) ?
C11 C8 C9 C17 . . . . 59.1(4) ?
C2 N1 C9A C9 . . . . -170.9(3) ?
C2 N1 C9A N5 . . . . 10.5(4) ?
C17 C9 C9A N1 . . . . 3.4(5) ?
C8 C9 C9A N1 . . . . 179.6(3) ?
C17 C9 C9A N5 . . . . -178.1(3) ?
C8 C9 C9A N5 . . . . -1.9(5) ?
C6 N5 C9A N1 . . . . 172.0(3) ?
C4 N5 C9A N1 . . . . -9.7(4) ?
C6 N5 C9A C9 . . . . -6.6(4) ?
C4 N5 C9A C9 . . . . 171.7(3) ?
C7 C8 C11 C12 . . . . 115.1(3) ?
C9 C8 C11 C12 . . . . -122.4(3) ?
C7 C8 C11 C16 . . . . -64.8(4) ?
C9 C8 C11 C16 . . . . 57.7(4) ?
C16 C11 C12 C13 . . . . -1.4(5) ?
C8 C11 C12 C13 . . . . 178.6(3) ?
C11 C12 C13 C14 . . . . 1.8(5) ?
C12 C13 C14 C15 . . . . -1.1(5) ?
C13 C14 C15 C16 . . . . 0.0(5) ?
C14 C15 C16 C11 . . . . 0.4(5) ?
C12 C11 C16 C15 . . . . 0.3(5) ?
C8 C11 C16 C15 . . . . -179.7(3) ?

_cod_database_fobs_code 2243797
