Crystal structure and Hirshfeld surface analysis of 1,6-diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
Naghiyev, Farid N.; Khrustalev, Victor N.; Akkurt, Mehmet; Khalilov, Ali N.; Bhattarai, Ajaya; Kerimli, Fuad Sh.; Mamedov, İbrahim G.; Acta Crystallographica Section E Crystallographic Communications 79 (2023) 494–498; doi:10.1107/S2056989023003237

data_2022749
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1,6-diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
;
_journal_coeditor_code           TX2066
_journal_issue                   5
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              494
_journal_page_last               498
_journal_paper_doi               10.1107/S2056989023003237
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C11 H7 N5 O S'
_chemical_formula_moiety         'C11 H7 N5 O S'
_chemical_formula_sum            'C11 H7 N5 O S'
_chemical_formula_weight         257.28
_chemical_name_systematic
;
1,6-Diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90.9441(9)
_cell_angle_beta                 104.1197(10)
_cell_angle_gamma                111.7451(10)
_cell_formula_units_Z            4
_cell_length_a                   8.94782(10)
_cell_length_b                   9.03908(9)
_cell_length_c                   14.87299(18)
_cell_measurement_reflns_used    26181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.78
_cell_measurement_theta_min      3.06
_cell_volume                     1075.92(2)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32558
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.279
_diffrn_reflns_theta_min         3.086
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.652
_exptl_absorpt_correction_T_max  0.561
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.457
_refine_ls_extinction_coef       0.0028(3)
_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   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.046P)^2^+1.11P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                4467
_reflns_number_total             4547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tx2066sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022749.cif.'
_cod_database_code               2022749
_cod_database_fobs_code          2022749
_shelx_estimated_absorpt_t_min   0.557
_shelx_estimated_absorpt_t_max   0.619
_shelx_hkl_checksum              28780
_shelx_res_checksum              44042
_shelxl_version_number           .2013