(E)-4-{2-[(2-Hy-droxy-naphthalen-1-yl)methyl-idene]hydrazinecarbon-yl}pyridinium nitrate.

The title compound, C(17)H(14)N(3)O(2) (+)·NO(3) (-), is an aroylhydrazone-based material consisting of a 4-(hydrazinecarbon-yl)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 intra-molecular O-H⋯N hydrogen bond in the cation, and the supra-molecular structure is stabilized by inter-molecular 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 Monfan class="Disease">red 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 +·n class="Chemical">NO3 −

M = 354.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.03

5046 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis n class="Disease">RED (Oxford Diffraction, 2003 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200061X/go2040sup1.cif

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

Supplementary material file. DOI: 10.1107/S160053681200061X/go2040Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H14N3O2+·NO3−	F(000) = 736
Mr = 354.32	Dx = 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

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

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(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
5046 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O1Aiv	0.95	2.28	3.1923 (16)	160.
C16—H16···O2Aiv	0.95	2.62	3.4553 (19)	147.

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⋯O1Aiv	0.95	2.28	3.1923 (16)	160
C16—H16⋯O2Aiv	0.95	2.62	3.4553 (19)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .