Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-4-{[2-(4-hydroxybenzoyl)hydrazin-1-ylidene]methyl}pyridin-1-ium nitrate
Naziri, Mir Abolfazl; Şahin, Ertan; Hökelek, Tuncer; Acta Crystallographica Section E 74 (2018) 323–327; doi:10.1107/S2056989018002141

data_2242374
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (<i>E</i>)-4-{[2-(4-hydroxybenzoyl)hydrazin-1-ylidene]methyl}pyridin-1-ium
 nitrate
;
_journal_coeditor_code           SU5422
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              323
_journal_page_last               327
_journal_paper_doi               10.1107/S2056989018002141
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H12 N3 O2 +, N O3 -'
_chemical_formula_moiety         'C13 H12 N3 O2 +, N O3 -'
_chemical_formula_sum            'C13 H12 N4 O5'
_chemical_formula_weight         304.27
_chemical_name_systematic
;
(<i>E</i>)-4-{[2-(4-Hydroxybenzoyl)hydrazin-1-ylidene]methyl}pyridin-1-ium
nitrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.902(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.335(3)
_cell_length_b                   13.929(5)
_cell_length_c                   12.184(4)
_cell_measurement_reflns_used    9700
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.12
_cell_volume                     1407.0(9)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2012)
;
_computing_data_collection
;
<i>APEX2</i> (Bruker, 2012)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2012)
;
_computing_molecular_graphics
;
<i>ORTEP-3</i> for Windows (Farrugia, 2012) and Mercury (Macrae <i>et
al.</i>,  2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
<i>SHELXL97</i> (Sheldrick, 2008)
;
_computing_structure_solution
;
<i>SHELXS97</i> (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44410
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.4149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1485
_reflns_number_gt                2508
_reflns_number_total             3499
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su5422sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1407.1(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2242374
_cod_database_fobs_code          2242374