(E)-4-{2-[(2-Hy­droxy­naphthalen-1-yl)methyl­idene]hydrazinecarbon­yl}pyridinium nitrate

Bikas, R.; Hosseini Monfared, H.; Lis, T.; Siczek, M.

doi:10.1107/S160053681200061X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o367-o368

doi:10.1107/S160053681200061X

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(E)-4-{2-[(2-Hydroxynaphthalen-1-yl)methylidene]hydrazinecarbonyl}pyridinium nitrate

Rahman Bikas,^a ^* Hassan Hosseini Monfared,^b Tadeusz Lis ^c and Milosz Siczek ^c

^aYoung Researchers Club, Tabriz Branch, Islamic Azad University, Tabriz, Iran, ^bDepartment of Chemistry, University of Zanjan, 45195-313, Zanjan, Iran, and ^cFaculty of Chemistry, University of Wroclaw, Joliot-Curie 14, Wroclaw 50-383, Poland
^*Correspondence e-mail: bikas_r@yahoo.com

(Received 20 December 2011; accepted 6 January 2012; online 11 January 2012)

The title compound, C₁₇H₁₄N₃O₂⁺·NO₃⁻, is an aroylhydrazone-based material consisting of a 4-(hydrazinecarbonyl)pyridinium cation and a nitrate anion. In the cation, the dihedral angle between the benzene ring and the naphthalene ring system is 2.20 (7)°. In the cation, the configuration about the C=N bond is E. There is an intramolecular O—H⋯N hydrogen bond in the cation, and the supramolecular structure is stabilized by intermolecular N—H⋯O hydrogen bonds and weak C—H⋯O contacts between the cation and the nitrate anion.

Related literature

For historical background to aroylhydrazones, see: Craliz et al. (1955 ). For related structures see: Bikas et al. (2010a ,b ); Hosseini Monfared et al. (2010a ); Abdel-Aziz et al. (2011 ). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008 ). For catalytic applications of aroylhydrazones, see: Hosseini Monfared et al. (2010b ). The overall structure of the cation is very similar to that found for free ligand, see: Richardson & Bernhardt (1999 ).

Experimental

Crystal data

C₁₇H₁₄N₃O₂⁺·NO₃⁻
M_r = 354.32
Monoclinic, P 2₁ /c
a = 8.695 (3) Å
b = 6.375 (2) Å
c = 28.955 (9) Å
β = 98.19 (4)°
V = 1588.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur PX kappa-geometry diffractometer with an Onyx CCD camera
12608 measured reflections
5046 independent reflections
3368 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.03
5046 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.82	2.5519 (15)	145
N2—H2⋯O3A	0.88	2.21	3.0332 (19)	155
N3—H3A⋯O1Aⁱ	0.88	1.80	2.6794 (14)	174
C14—H14⋯O3A	0.95	2.26	3.1528 (16)	156
C8—H8⋯O2ⁱⁱ	0.95	2.60	3.2449 (19)	125
C15—H15⋯O2Aⁱⁱⁱ	0.95	2.61	3.3089 (19)	130
C16—H16⋯O1A^iv	0.95	2.28	3.1923 (16)	160
C16—H16⋯O2A^iv	0.95	2.62	3.4553 (19)	147
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y-1, z; (iii) x, y+1, z; (iv) x+1, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wrocław, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wrocław, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681200061X/go2040sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200061X/go2040Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200061X/go2040Isup3.cml

checkCIF report

Comment top

Hydrazone ligands, a class of Schiff base, derived from the condensation of acid hydrazides (R–CO–NH–NH₂) with aromatic 2-hydroxy carbonyl compounds are important tridentate O, N, O-donor ligands. As biologically active compounds, hydrazones find application in the treatment of diseases such as anti-tumor, tuberculosis, leprosy and mental disorder. Hydrazone ligands create environment similar to biological systems by usually making coordination through oxygen and nitrogen atoms. Furthermore hydrazones have wide spread applications in fields such as coordination chemistry, bioinorganic chemistry, in magnetic, electronic, nonlinear optically active and fluorescent compounds. Aroylhydrazone complexes seem to be a good candidate for catalytic oxidation studies because of their resist to oxidation (Hosseini Monfared et al., 2010b).

As part of our studies on the synthesis and characterization of hydrazone derivatives, we report here the crystal structure of (E)-4-(2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinecarbonyl)pyridinium nitrate. The asymmetric unit of C₁₇H₁₄N₄O₅, consists of a (E)-4-(2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinecarbonyl)pyridinium cation and a nitrate anion (Fig. 1). The dihedral angle between the mean planes of the benzene and naphthalene rings is 2.20 (7)°. The cation displays a trans configuration with respect to the C=N and N—N bonds. It is to note that the overall structure of the cation is very similar to that found for free ligand Richardson & Bernhardt (1999). The packing diagram of the title compound is shown in Fig. 2. There is a strong intramolecular O—H···N hydrogen bond in which the N of the azomethine group (–C=N–) acts as hydrogen acceptor for the hydrogen O—H group attached to the naphthalene ring. Two intermolecular N—H···O hydrogen bonds are formed between cation and anion where NO₃^- acts as hydrogen bonds acceptor (Fig. 3). The supramolecular structure is further stabilised by C—H···O interactions.

Related literature top

For historical background to aroylhydrazones, see: Craliz et al. (1955). For related structures see: Bikas et al. (2010a,b); Hosseini Monfared et al. (2010a); Abdel-Aziz et al. (2011). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008). For catalytic applications of aroylhydrazones, see: Hosseini Monfared et al. (2010b).

For related literature, see: Richardson & Bernhardt (1999).

Experimental top

All reagents were commercially available and used as received. A methanol (10 ml) solution of 2-hydroxy-1-naphthaldehyde (1.63 mmol) was dropwise added to a methanol solution (10 ml) of 4-pyridine carboxylic acid hydrazide (1.63 mmol), and the mixture was refluxed for 3 hrs. Then the solution was evaporated on a steam bath to 5 ml and cooled to room temperature. The resultant yellow precipitate was separated and filtered off, washed with 5 ml of cooled methanol and then dried in air. 1 mmol of this solid was placed in one arm of a branched tube with 2 mmol of Mn(NO₃)₂.4H₂O. Methanol was carefully added to fill the arms, the tube was sealed and the arm containing the reagents was immersed in an oil bath at 60 °C while the other arm was kept at ambient temperature. After 4 days, crystals were deposited in the cooler arm, which were filtered off and air dried. Yield: 85%, Selected IR spectrum: 3430 (s, broad), 1630 (s), 1600 (m), 1549 (m), 1384 (versus), 1291 (m), 972 (m), 834 (s), 764 cm^-1 (m).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with labelling scheme and anisotropic displacement ellipsoids (drawn at 30% probability level for non-H atoms).
	Fig. 2. The packing diagram of the title compound.
	Fig. 3. A diagram showing formation of intra- (O–H···N) and intermolecular (N–H···O) hydrogen bonds between anions and cations.

(E)-4-{2-[(2-Hydroxynaphthalen-1- yl)methylidene]hydrazinecarbonyl}pyridinium nitrate top

Crystal data top

C₁₇H₁₄N₃O₂⁺·NO₃⁻	F(000) = 736
M_r = 354.32	D_x = 1.481 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4462 reflections
a = 8.695 (3) Å	θ = 2–70°
b = 6.375 (2) Å	µ = 0.11 mm⁻¹
c = 28.955 (9) Å	T = 100 K
β = 98.19 (4)°	Needle, orange
V = 1588.6 (9) Å³	0.30 × 0.10 × 0.07 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur PX kappa-geometry diffractometer with an Onyx CCD camera	3368 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 31.1°, θ_min = 2.6°
ω and phi scans	h = −12→12
12608 measured reflections	k = −8→9
5046 independent reflections	l = −42→35

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.048P)²] where P = (F_o² + 2F_c²)/3
5046 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₄N₃O₂⁺·NO₃⁻	V = 1588.6 (9) Å³
M_r = 354.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.695 (3) Å	µ = 0.11 mm⁻¹
b = 6.375 (2) Å	T = 100 K
c = 28.955 (9) Å	0.30 × 0.10 × 0.07 mm
β = 98.19 (4)°

Data collection top

Oxford Diffraction Xcalibur PX kappa-geometry diffractometer with an Onyx CCD camera	3368 reflections with I > 2σ(I)
12608 measured reflections	R_int = 0.030
5046 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
5046 reflections	Δρ_min = −0.22 e Å⁻³
236 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.97012 (9)	0.07072 (13)	0.68081 (3)	0.02035 (19)
H1	0.9395	0.1749	0.6642	0.031*
C1	0.69254 (13)	0.00322 (16)	0.67027 (4)	0.0134 (2)
C2	0.84656 (13)	−0.04806 (17)	0.68768 (4)	0.0157 (2)
C3	0.88242 (14)	−0.23367 (17)	0.71408 (4)	0.0183 (2)
H3	0.9873	−0.2643	0.7263	0.022*
C4	0.76730 (14)	−0.36810 (17)	0.72201 (4)	0.0182 (2)
H4	0.7931	−0.4913	0.7399	0.022*
C5	0.60945 (14)	−0.32776 (17)	0.70405 (4)	0.0160 (2)
C6	0.49134 (15)	−0.47202 (18)	0.71132 (4)	0.0196 (3)
H6	0.5186	−0.5988	0.7277	0.023*
C7	0.33824 (15)	−0.43169 (19)	0.69510 (5)	0.0229 (3)
H7	0.2600	−0.5301	0.6998	0.028*
C8	0.29866 (14)	−0.2422 (2)	0.67130 (4)	0.0229 (3)
H8	0.1924	−0.2118	0.6608	0.028*
C9	0.41042 (14)	−0.10038 (18)	0.66288 (4)	0.0189 (2)
H9	0.3803	0.0250	0.6463	0.023*
C10	0.57040 (13)	−0.13845 (16)	0.67860 (4)	0.0143 (2)
C11	0.65724 (13)	0.19520 (17)	0.64348 (4)	0.0149 (2)
H11	0.5526	0.2348	0.6332	0.018*
N1	0.77034 (11)	0.31000 (14)	0.63397 (3)	0.0160 (2)
N2	0.73812 (12)	0.49164 (14)	0.60861 (3)	0.0163 (2)
H2	0.6425	0.5334	0.5989	0.020*
C12	0.86518 (13)	0.60206 (17)	0.59968 (4)	0.0166 (2)
O2	0.99749 (10)	0.53944 (13)	0.61115 (3)	0.0244 (2)
C13	0.83618 (13)	0.80954 (16)	0.57479 (4)	0.0151 (2)
C14	0.69062 (14)	0.88961 (17)	0.55696 (4)	0.0172 (2)
H14	0.5987	0.8157	0.5611	0.021*
C15	0.68192 (14)	1.07777 (17)	0.53318 (4)	0.0181 (2)
H15	0.5834	1.1331	0.5205	0.022*
N3	0.81220 (12)	1.18318 (14)	0.52782 (3)	0.0178 (2)
H3A	0.8043	1.3007	0.5117	0.021*
C16	0.95343 (14)	1.11540 (18)	0.54613 (4)	0.0198 (3)
H16	1.0429	1.1970	0.5431	0.024*
C17	0.96832 (14)	0.92589 (18)	0.56950 (4)	0.0188 (2)
H17	1.0684	0.8750	0.5819	0.023*
N1A	0.32288 (12)	0.41051 (15)	0.54333 (4)	0.0204 (2)
O1A	0.19647 (10)	0.44786 (12)	0.51679 (3)	0.0205 (2)
O2A	0.34501 (10)	0.23488 (14)	0.56160 (3)	0.0273 (2)
O3A	0.42367 (12)	0.55145 (16)	0.54972 (4)	0.0453 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0168 (4)	0.0201 (4)	0.0232 (5)	−0.0038 (3)	−0.0003 (3)	0.0040 (3)
C1	0.0172 (5)	0.0125 (5)	0.0104 (5)	0.0002 (4)	0.0017 (4)	−0.0002 (4)
C2	0.0177 (5)	0.0165 (5)	0.0127 (6)	−0.0016 (4)	0.0017 (4)	−0.0028 (4)
C3	0.0187 (5)	0.0203 (5)	0.0150 (6)	0.0039 (5)	−0.0004 (4)	0.0008 (5)
C4	0.0249 (6)	0.0159 (5)	0.0137 (6)	0.0046 (5)	0.0025 (5)	0.0028 (4)
C5	0.0225 (6)	0.0144 (5)	0.0117 (6)	0.0010 (4)	0.0050 (4)	0.0001 (4)
C6	0.0274 (6)	0.0158 (5)	0.0166 (6)	−0.0003 (5)	0.0067 (5)	0.0021 (5)
C7	0.0239 (6)	0.0231 (6)	0.0232 (7)	−0.0070 (5)	0.0081 (5)	0.0024 (5)
C8	0.0177 (6)	0.0284 (6)	0.0221 (7)	−0.0032 (5)	0.0009 (5)	0.0031 (5)
C9	0.0192 (5)	0.0191 (5)	0.0177 (6)	−0.0001 (5)	0.0006 (5)	0.0051 (5)
C10	0.0175 (5)	0.0144 (5)	0.0113 (6)	−0.0002 (4)	0.0027 (4)	−0.0003 (4)
C11	0.0180 (5)	0.0135 (5)	0.0128 (6)	0.0000 (4)	0.0014 (4)	−0.0008 (4)
N1	0.0217 (5)	0.0116 (4)	0.0144 (5)	−0.0010 (4)	0.0020 (4)	0.0012 (4)
N2	0.0192 (5)	0.0128 (4)	0.0168 (5)	−0.0009 (4)	0.0018 (4)	0.0038 (4)
C12	0.0210 (6)	0.0139 (5)	0.0147 (6)	−0.0037 (4)	0.0021 (4)	−0.0015 (4)
O2	0.0194 (4)	0.0202 (4)	0.0327 (6)	−0.0015 (3)	0.0008 (4)	0.0044 (4)
C13	0.0201 (5)	0.0132 (5)	0.0122 (6)	−0.0030 (4)	0.0033 (4)	−0.0009 (4)
C14	0.0200 (5)	0.0153 (5)	0.0160 (6)	−0.0057 (4)	0.0019 (4)	−0.0007 (4)
C15	0.0210 (6)	0.0167 (5)	0.0162 (6)	−0.0030 (5)	0.0014 (5)	−0.0010 (4)
N3	0.0249 (5)	0.0146 (4)	0.0141 (5)	−0.0048 (4)	0.0030 (4)	0.0016 (4)
C16	0.0212 (6)	0.0194 (5)	0.0193 (6)	−0.0064 (5)	0.0051 (5)	−0.0002 (5)
C17	0.0193 (6)	0.0192 (5)	0.0178 (6)	−0.0033 (5)	0.0025 (5)	0.0006 (5)
N1A	0.0182 (5)	0.0218 (5)	0.0207 (6)	−0.0045 (4)	0.0011 (4)	0.0028 (4)
O1A	0.0169 (4)	0.0208 (4)	0.0223 (5)	−0.0037 (3)	−0.0020 (3)	0.0052 (3)
O2A	0.0274 (5)	0.0225 (4)	0.0304 (6)	0.0001 (4)	−0.0009 (4)	0.0091 (4)
O3A	0.0312 (6)	0.0385 (6)	0.0590 (8)	−0.0226 (5)	−0.0178 (5)	0.0197 (5)

Geometric parameters (Å, º) top

O1—C2	1.3521 (14)	C11—H11	0.9500
O1—H1	0.8400	N1—N2	1.3784 (13)
C1—C2	1.4007 (16)	N2—C12	1.3654 (15)
C1—C10	1.4404 (16)	N2—H2	0.8800
C1—C11	1.4581 (16)	C12—O2	1.2183 (14)
C2—C3	1.4192 (16)	C12—C13	1.5101 (16)
C3—C4	1.3618 (17)	C13—C14	1.3938 (17)
C3—H3	0.9500	C13—C17	1.3942 (16)
C4—C5	1.4202 (17)	C14—C15	1.3799 (16)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.4165 (17)	C15—N3	1.3449 (15)
C5—C10	1.4295 (16)	C15—H15	0.9500
C6—C7	1.3714 (18)	N3—C16	1.3380 (16)
C6—H6	0.9500	N3—H3A	0.8800
C7—C8	1.4091 (18)	C16—C17	1.3818 (17)
C7—H7	0.9500	C16—H16	0.9500
C8—C9	1.3741 (17)	C17—H17	0.9500
C8—H8	0.9500	N1A—O2A	1.2416 (13)
C9—C10	1.4215 (16)	N1A—O3A	1.2503 (13)
C9—H9	0.9500	N1A—O1A	1.2706 (13)
C11—N1	1.2867 (15)

C2—O1—H1	109.5	N1—C11—C1	118.81 (10)
C2—C1—C10	118.90 (10)	N1—C11—H11	120.6
C2—C1—C11	120.36 (10)	C1—C11—H11	120.6
C10—C1—C11	120.73 (10)	C11—N1—N2	119.23 (10)
O1—C2—C1	123.73 (10)	C12—N2—N1	115.18 (10)
O1—C2—C3	115.34 (10)	C12—N2—H2	122.4
C1—C2—C3	120.93 (11)	N1—N2—H2	122.4
C4—C3—C2	120.34 (11)	O2—C12—N2	122.52 (11)
C4—C3—H3	119.8	O2—C12—C13	120.27 (11)
C2—C3—H3	119.8	N2—C12—C13	117.21 (10)
C3—C4—C5	121.30 (11)	C14—C13—C17	118.91 (10)
C3—C4—H4	119.4	C14—C13—C12	125.35 (10)
C5—C4—H4	119.4	C17—C13—C12	115.73 (10)
C6—C5—C4	120.75 (10)	C15—C14—C13	119.05 (11)
C6—C5—C10	120.05 (11)	C15—C14—H14	120.5
C4—C5—C10	119.20 (11)	C13—C14—H14	120.5
C7—C6—C5	121.08 (11)	N3—C15—C14	120.31 (11)
C7—C6—H6	119.5	N3—C15—H15	119.8
C5—C6—H6	119.5	C14—C15—H15	119.8
C6—C7—C8	119.07 (11)	C16—N3—C15	122.24 (10)
C6—C7—H7	120.5	C16—N3—H3A	118.9
C8—C7—H7	120.5	C15—N3—H3A	118.9
C9—C8—C7	121.41 (11)	N3—C16—C17	119.54 (11)
C9—C8—H8	119.3	N3—C16—H16	120.2
C7—C8—H8	119.3	C17—C16—H16	120.2
C8—C9—C10	121.03 (11)	C16—C17—C13	119.85 (11)
C8—C9—H9	119.5	C16—C17—H17	120.1
C10—C9—H9	119.5	C13—C17—H17	120.1
C9—C10—C5	117.31 (10)	O2A—N1A—O3A	121.47 (11)
C9—C10—C1	123.41 (10)	O2A—N1A—O1A	119.66 (10)
C5—C10—C1	119.28 (10)	O3A—N1A—O1A	118.85 (10)

C10—C1—C2—O1	178.17 (10)	C11—C1—C10—C9	−1.70 (17)
C11—C1—C2—O1	−0.78 (18)	C2—C1—C10—C5	−0.43 (16)
C10—C1—C2—C3	−1.51 (17)	C11—C1—C10—C5	178.51 (11)
C11—C1—C2—C3	179.55 (11)	C2—C1—C11—N1	3.82 (17)
O1—C2—C3—C4	−178.13 (11)	C10—C1—C11—N1	−175.10 (11)
C1—C2—C3—C4	1.57 (18)	C1—C11—N1—N2	179.91 (10)
C2—C3—C4—C5	0.38 (18)	C11—N1—N2—C12	−179.21 (10)
C3—C4—C5—C6	178.04 (12)	N1—N2—C12—O2	3.65 (17)
C3—C4—C5—C10	−2.30 (18)	N1—N2—C12—C13	−176.03 (9)
C4—C5—C6—C7	178.34 (12)	O2—C12—C13—C14	174.93 (12)
C10—C5—C6—C7	−1.32 (18)	N2—C12—C13—C14	−5.38 (17)
C5—C6—C7—C8	−0.71 (19)	O2—C12—C13—C17	−4.57 (17)
C6—C7—C8—C9	1.9 (2)	N2—C12—C13—C17	175.11 (10)
C7—C8—C9—C10	−1.0 (2)	C17—C13—C14—C15	2.30 (17)
C8—C9—C10—C5	−1.02 (18)	C12—C13—C14—C15	−177.18 (11)
C8—C9—C10—C1	179.19 (12)	C13—C14—C15—N3	−0.78 (18)
C6—C5—C10—C9	2.15 (17)	C14—C15—N3—C16	−2.04 (18)
C4—C5—C10—C9	−177.51 (11)	C15—N3—C16—C17	3.20 (18)
C6—C5—C10—C1	−178.04 (11)	N3—C16—C17—C13	−1.54 (18)
C4—C5—C10—C1	2.30 (17)	C14—C13—C17—C16	−1.17 (18)
C2—C1—C10—C9	179.36 (11)	C12—C13—C17—C16	178.37 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.82	2.5519 (15)	145
N2—H2···O3A	0.88	2.21	3.0332 (19)	155
N3—H3A···O1Aⁱ	0.88	1.80	2.6794 (14)	174
C14—H14···O3A	0.95	2.26	3.1528 (16)	156
C8—H8···O2ⁱⁱ	0.95	2.60	3.2449 (19)	125
C15—H15···O2Aⁱⁱⁱ	0.95	2.61	3.3089 (19)	130
C16—H16···O1A^iv	0.95	2.28	3.1923 (16)	160
C16—H16···O2A^iv	0.95	2.62	3.4553 (19)	147

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y−1, z; (iii) x, y+1, z; (iv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₃O₂⁺·NO₃⁻
M_r	354.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.695 (3), 6.375 (2), 28.955 (9)
β (°)	98.19 (4)
V (Å³)	1588.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.10 × 0.07

Data collection
Diffractometer	Oxford Diffraction Xcalibur PX kappa-geometry diffractometer with an Onyx CCD camera
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12608, 5046, 3368
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.726

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.03
No. of reflections	5046
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.22

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.82	2.5519 (15)	144.9
N2—H2···O3A	0.88	2.21	3.0332 (19)	155.3
N3—H3A···O1Aⁱ	0.88	1.80	2.6794 (14)	174.1
C14—H14···O3A	0.95	2.26	3.1528 (16)	155.7
C8—H8···O2ⁱⁱ	0.95	2.60	3.2449 (19)	125.4
C15—H15···O2Aⁱⁱⁱ	0.95	2.61	3.3089 (19)	130.3
C16—H16···O1A^iv	0.95	2.28	3.1923 (16)	160.1
C16—H16···O2A^iv	0.95	2.62	3.4553 (19)	147.4

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y−1, z; (iii) x, y+1, z; (iv) x+1, y+1, z.

Acknowledgements

The authors are grateful to the Islamic Azad Uinversity, Tabriz Branch, and the University of Zanjan for financial support of this study.

References

Abdel-Aziz, H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2317–o2318. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Carvalho, S. R., da Silva, E. F., de Souza, M. V. N., Lourenco, M. C. S. & Vicente, F. R. (2008). Bioorg. Med. Chem. Lett. 18, 538-541. Web of Science CrossRef PubMed CAS Google Scholar
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Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wrocław, Poland. Google Scholar
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Volume 68| Part 2| February 2012| Pages o367-o368

doi:10.1107/S160053681200061X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-4-{2-[(2-Hy­dr­oxy­naphthalen-1-yl)methyl­­idene]hydrazinecarbon­yl}pyridinium nitrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-4-{2-[(2-Hydroxynaphthalen-1-yl)methylidene]hydrazinecarbonyl}pyridinium nitrate