Crystal structure and Hirshfeld surface analysis of 6-amino-8-phenyl-1,3,4,8-tetrahydro-2<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidine-7,9-dicarbonitrile
Naghiyev, Farid N.; Tereshina, Tatiana A.; Khrustalev, Victor N.; Akkurt, Mehmet; Khalilov, Ali N.; Akobirshoeva, Anzurat A.; Mamedov, İbrahim G.; Acta Crystallographica Section E 77 (2021) 512–515; doi:10.1107/S2056989021003625

data_2243797
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 6-amino-8-phenyl-1,3,4,8-tetrahydro-2<i>H</i>-pyrido[1,2-<i>a</i>]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-2<i>H</i>-pyrido[1,2-<i>a</i>]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
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (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       '\f and \w 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 <i>et al.</i>,  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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0647P)^2^+0.4109P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_cod_database_fobs_code          2243797
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.997
_shelx_hkl_checksum              38431
_shelx_res_checksum              57300
_shelxl_version_number           .2013