#------------------------------------------------------------------------------
#$Date: 2018-02-08 09:56:03 +0200 (Thu, 08 Feb 2018) $
#$Revision: 206297 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242374.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_2242374
loop_
_publ_author_name
'Naziri, Mir Abolfazl'
'Şahin, Ertan'
'Hökelek, Tuncer'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (E)-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
;
(E)-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
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et
al.,  2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (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       'φ and ω 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
;
(SADABS; 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/[σ²(Fo²)+(0.0782P)²+0.4149P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 1.15687(19) 0.08055(9) 0.24127(12) 0.0576(4) Uani d . 1 1
H H1A 1.207(3) 0.1109(18) 0.183(2) 0.080(8) Uiso d . 1 1
O O2 0.82328(18) 0.32288(9) 0.59284(11) 0.0549(4) Uani d . 1 1
O O3 0.3316(2) 0.99298(10) 0.57667(11) 0.0619(4) Uani d . 1 1
O O4 0.37385(19) 0.95570(10) 0.74819(11) 0.0595(4) Uani d . 1 1
O O5 0.22205(19) 1.07556(11) 0.69841(15) 0.0730(5) Uani d . 1 1
N N1 0.81569(17) 0.43407(10) 0.45738(12) 0.0392(3) Uani d . 1 1
H H1B 0.830(3) 0.4512(15) 0.3928(19) 0.055(6) Uiso d . 1 1
N N2 0.74051(16) 0.49881(10) 0.51883(11) 0.0368(3) Uani d . 1 1
N N3 0.50122(17) 0.80177(10) 0.64341(12) 0.0408(3) Uani d . 1 1
H H3A 0.456(3) 0.8548(17) 0.6811(19) 0.069(7) Uiso d . 1 1
N N4 0.30832(18) 1.00915(10) 0.67253(13) 0.0438(4) Uani d . 1 1
C C1 1.08209(19) 0.24460(12) 0.27240(13) 0.0367(4) Uani d . 1 1
H H1 1.1286 0.2655 0.2104 0.044 Uiso calc R 1 1
C C2 1.0865(2) 0.14803(12) 0.30031(14) 0.0386(4) Uani d . 1 1
C C3 1.0173(2) 0.11743(13) 0.39341(15) 0.0452(4) Uani d . 1 1
H H3 1.0208 0.0528 0.4129 0.054 Uiso calc R 1 1
C C4 0.9439(2) 0.18265(12) 0.45671(14) 0.0410(4) Uani d . 1 1
H H4 0.8980 0.1616 0.5189 0.049 Uiso calc R 1 1
C C5 0.93716(18) 0.27990(11) 0.42900(13) 0.0334(3) Uani d . 1 1
C C6 1.00883(18) 0.30970(12) 0.33645(13) 0.0353(4) Uani d . 1 1
H H6 1.0073 0.3744 0.3176 0.042 Uiso calc R 1 1
C C7 0.85500(18) 0.34613(11) 0.50025(13) 0.0352(3) Uani d . 1 1
C C8 0.7030(2) 0.57893(12) 0.47233(14) 0.0417(4) Uani d . 1 1
H H8 0.7236 0.5893 0.3997 0.050 Uiso calc R 1 1
C C9 0.62801(18) 0.65447(11) 0.53250(13) 0.0347(3) Uani d . 1 1
C C10 0.56331(19) 0.63741(12) 0.63168(14) 0.0377(4) Uani d . 1 1
H H10 0.5629 0.5758 0.6610 0.045 Uiso calc R 1 1
C C11 0.5004(2) 0.71264(12) 0.68521(15) 0.0402(4) Uani d . 1 1
H H11 0.4565 0.7019 0.7513 0.048 Uiso calc R 1 1
C C12 0.5620(2) 0.82024(12) 0.54903(15) 0.0441(4) Uani d . 1 1
H H12 0.5613 0.8827 0.5221 0.053 Uiso calc R 1 1
C C13 0.6257(2) 0.74791(12) 0.49147(14) 0.0401(4) Uani d . 1 1
H H13 0.6673 0.7610 0.4251 0.048 Uiso calc R 1 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'
O O 0.0106 0.0060 '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
C2 O1 H1A 109.6(15)
N2 N1 H1B 116.3(15)
C7 N1 N2 119.41(14)
C7 N1 H1B 124.2(15)
C8 N2 N1 116.08(14)
C11 N3 H3A 120.6(14)
C12 N3 C11 121.66(15)
C12 N3 H3A 117.7(14)
O3 N4 O4 119.23(15)
O3 N4 O5 122.40(17)
O5 N4 O4 118.37(16)
C2 C1 H1 120.0
C6 C1 C2 120.06(14)
C6 C1 H1 120.0
O1 C2 C1 123.03(15)
O1 C2 C3 117.33(16)
C1 C2 C3 119.64(15)
C2 C3 H3 120.0
C4 C3 C2 120.02(16)
C4 C3 H3 120.0
C3 C4 C5 120.96(15)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C7 118.16(14)
C6 C5 C4 118.38(14)
C6 C5 C7 123.46(15)
C1 C6 C5 120.92(15)
C1 C6 H6 119.5
C5 C6 H6 119.5
O2 C7 N1 121.65(15)
O2 C7 C5 122.00(15)
N1 C7 C5 116.35(14)
N2 C8 C9 120.38(15)
N2 C8 H8 119.8
C9 C8 H8 119.8
C10 C9 C8 122.46(15)
C10 C9 C13 118.54(14)
C13 C9 C8 118.96(15)
C9 C10 H10 120.5
C11 C10 C9 119.00(15)
C11 C10 H10 120.5
N3 C11 C10 120.71(16)
N3 C11 H11 119.6
C10 C11 H11 119.6
N3 C12 C13 120.30(16)
N3 C12 H12 119.9
C13 C12 H12 119.9
C9 C13 H13 120.1
C12 C13 C9 119.79(15)
C12 C13 H13 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.354(2)
O1 H1A 0.96(3)
O2 C7 1.228(2)
O3 N4 1.224(2)
O4 N4 1.264(2)
N1 C7 1.359(2)
N1 H1B 0.84(2)
N2 N1 1.3649(19)
N2 C8 1.276(2)
N3 C11 1.342(2)
N3 C12 1.329(2)
N3 H3A 0.97(2)
N4 O5 1.2325(19)
C1 H1 0.9300
C2 C1 1.387(2)
C2 C3 1.391(2)
C3 H3 0.9300
C4 C3 1.376(2)
C4 H4 0.9300
C5 C4 1.396(2)
C5 C6 1.393(2)
C5 C7 1.482(2)
C6 C1 1.379(2)
C6 H6 0.9300
C8 H8 0.9300
C9 C8 1.459(2)
C9 C10 1.393(2)
C9 C13 1.394(2)
C10 C11 1.367(2)
C10 H10 0.9300
C11 H11 0.9300
C12 H12 0.9300
C13 C12 1.366(2)
C13 H13 0.9300
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 H10 2.48 4_665 yes
O2 H1 2.58 4_566 yes
O2 H1A 1.79(2) 4_566 yes
O2 H4 2.52 . yes
O3 H3A 2.48(2) . yes
O3 H12 2.59 . yes
O4 H3A 1.80(2) . yes
N1 H6 2.59 . yes
N2 H1A 2.56(2) 4_566 yes
N2 H10 2.62 . yes
N4 H3A 2.47(2) . yes
C6 H1B 2.61(2) . yes
C7 H1A 2.72(2) 4_566 yes
H1 H1A 2.28 . yes
H1B O4 2.25(2) 4_675 yes
H1B O5 2.47(2) 4_675 yes
H1B N4 2.73(2) 4_675 yes
H6 O4 2.71 4_675 yes
H6 O5 2.75 4_675 yes
H6 N4 2.81 4_675 yes
H6 H1B 2.11 . yes
H8 O4 2.42 4_675 yes
H8 H1B 2.12 . yes
H8 H13 2.46 . yes
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
O1 H1A O2 4_665 0.96(2) 1.79(2) 2.742(2) 170(2) yes
N1 H1B O4 4_675 0.84(2) 2.25(2) 3.057(2) 161(2) yes
N1 H1B O5 4_675 0.84(2) 2.47(2) 3.174(3) 141(2) yes
N3 H3A O4 . 0.97(2) 1.80(2) 2.763(2) 178(2) yes
C1 H1 O2 4_665 0.93 2.58 3.258(2) 130 yes
C8 H8 O4 4_675 0.93 2.42 3.243(2) 148 yes
C10 H10 O1 4_566 0.93 2.48 3.375(2) 162 yes
C11 H11 O5 2_546 0.93 2.42 3.104(3) 130 yes
C12 H12 O3 3_676 0.93 2.34 3.191(2) 152 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
N2 N1 C7 O2 0.7(2)
N2 N1 C7 C5 -179.66(13)
C8 N2 N1 C7 -178.09(15)
N1 N2 C8 C9 -177.58(14)
C12 N3 C11 C10 0.3(3)
C11 N3 C12 C13 0.1(3)
O1 C2 C1 C6 -179.76(15)
C3 C2 C1 C6 -0.3(3)
O1 C2 C3 C4 -179.94(17)
C1 C2 C3 C4 0.6(3)
C5 C4 C3 C2 0.0(3)
C6 C5 C4 C3 -0.9(3)
C7 C5 C4 C3 179.50(16)
C4 C5 C6 C1 1.2(2)
C7 C5 C6 C1 -179.26(15)
C4 C5 C7 O2 15.3(2)
C4 C5 C7 N1 -164.34(15)
C6 C5 C7 O2 -164.23(16)
C6 C5 C7 N1 16.1(2)
C5 C6 C1 C2 -0.6(2)
C10 C9 C8 N2 -13.9(3)
C13 C9 C8 N2 163.87(16)
C8 C9 C10 C11 177.61(16)
C13 C9 C10 C11 -0.1(2)
C8 C9 C13 C12 -177.27(16)
C10 C9 C13 C12 0.6(2)
C9 C10 C11 N3 -0.3(3)
C9 C13 C12 N3 -0.6(3)

_cod_database_fobs_code 2242374
