3-{[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium per­chlorate

Damous, M.; Dénès, G.; Bouacida, S.; Hamlaoui, M.; Merazig, H.; Daran, J.-C.

doi:10.1107/S1600536813023015

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Pages o1460-o1461

doi:10.1107/S1600536813023015

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3-{[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium perchlorate

Maamar Damous,^a George Dénès,^b Sofiane Bouacida,^a,^c ^* Meriem Hamlaoui,^a Hocine Merazig ^a and Jean-Claude Daran ^d

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000, Algeria, ^bLaboratory of Solid State Chemistry and Mössbauer Spectroscopy, Laboratories for Inorganic Materials, Department of Chemistry and Biochemistry, Concordia University, Montreal, Quebec, H3G 1M8, Canada, ^cDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi 04000, Algeria, and ^dLaboratoire de Chimie de Coordination, UPR CNRS 8241, 205 route de Narbonne, 31077 Toulouse cedex, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 10 August 2013; accepted 15 August 2013; online 21 August 2013)

In the title Schiff base salt, C₁₆H₁₃N₂O⁺·ClO₄⁻, the pyridine ring and the naphthalene ring system are approximately co-planar [making a dihedral angle of 6.05 (12)°] and an intramolecular O—H⋯N hydrogen bond occurs between the hydroxyl and imino groups. In the crystal, the cations and anions are linked by N—H⋯O and weak C—H⋯O hydrogen bonds, forming the supramolecular layers parallel to (100). The crystal studied was an inversion twin refined with minor component = 0.43 (13).

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000 ); Sriram et al. (2006 ); Karthikeyan et al. (2006 ). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 ); Kargar et al. (2009 ); Yeap et al. (2009 ). For the crystal structures of related Schiff base compounds, see: Damous et al. (2011 ); Fun et al. (2009 ); Nadeem et al. (2009 ); Eltayeb et al. (2008 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₆H₁₃N₂O⁺·ClO₄⁻
M_r = 348.73
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.5043 (9) Å
b = 14.6915 (19) Å
c = 15.398 (3) Å
V = 1471.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 180 K
0.25 × 0.04 × 0.03 mm

Data collection

Agilent Xcalibur (Sapphire1) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.685, T_max = 1.000
9582 measured reflections
3369 independent reflections
1695 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.127
S = 0.92
3369 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1362 Friedel pairs
Absolute structure parameter: 0.43 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.545 (4)	147
N5—H5⋯O13ⁱ	0.86	2.09	2.844 (5)	146
C2—H2⋯O11	0.93	2.44	3.354 (5)	166
C3—H3⋯O1ⁱⁱ	0.93	2.59	3.260 (5)	129
C13—H13⋯O12ⁱⁱⁱ	0.93	2.57	3.451 (6)	158
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813023015/xu5730sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023015/xu5730Isup2.hkl

checkCIF report

Comment top

Schiff base compounds are a class of important materials used as pharmaceuticals and in various medicinal fields of interest (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). Schiff bases have also been used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of a large number of new Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008; Damous et al., 2011).

Herein we report the synthesis and crystal structure of 3-{[E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium perchlorate, (I). The molecular structure of (I), and the atomic numbering used, is illustrated in Fig. 1. The asymmetric unit of (I) consists of one protoned N-(3-pyridil)-2-oxo-1-naphthylidenemethylamine cation and one perchlorate anion. All bond distances and angles are within the ranges of accepted values(CSD, Allen, 2002). The cation is co-planar with r.m.s. deviation all non-H atoms, for cation, are essentially co-planar with a maximum deviation of -0.1158 (39) Å for N5 [r.m.s. deviation: 0.0590 Å]. The molecule is twisted with the dihedral angle between the benzene and the naphthyl ring mean planes being 6.05 (12) °.

In the crystal structure, cationic and anionic layers alternate along the c axis and are linked by intermolecular N—H···O and weak C—H···O hydrogen bonds (Table 1, Fig.2) resulting in a two-dimensional network parallel to (100)plane (Fig.3). Also, we observe an intramolecular O—H···N hydrogen bond, involving the naphthalene hydroxyl substituent and the pyridine N-atom (Fig.1, Table 1).

Related literature top

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000); Sriram et al. (2006); Karthikeyan et al. (2006). For the coordination chemistry of Schiff bases, see: Ali et al. (2008); Kargar et al. (2009); Yeap et al. (2009). For the crystal structures of related Schiff base compounds, see: Damous et al. (2011); Fun et al. (2009); Nadeem et al. (2009); Eltayeb et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The title compound, (I), was prepared by refluxing a mixture of a solution containing (0.1 mmol) of 2-hydroxy-1-naphthaldehyde and (0.1 mmol) of 3-aminopyridine in presence of perchloric acid in 20 ml methanol. The reaction mixture was stirred for 1 h under reflux. Microcrystals of (I) were obtained by allowing the clear solution to stand overnight. The powder product was dissolved and recrystallized from DMSO solution. Some red crystals were carefully isolated under polarizing microscope for analysis by X-ray diffraction.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX publication routines (Farrugia, 1012).

Figures top

	Fig. 1. The molecule structure of the title compound with the atomic labelling scheme (Farrugia, 2012). Displacement are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius. Intramolecular hydrogen bond O—H···N is showing as dashed line.
	Fig. 2. Hydrogen bond connections as dashed line in the same layers parallel to (100) plane between cations and anions (Brandenburg & Berndt, 2001).
	Fig. 3. A diagram of the layered crystal packing in (I), viewed down the b axis showing hydrogen bond as dashed line (Brandenburg & Berndt, 2001)

3-{[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium perchlorate top

Crystal data top

C₁₆H₁₃N₂O⁺·ClO₄⁻	D_x = 1.574 Mg m⁻³
M_r = 348.73	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1867 reflections
a = 6.5043 (9) Å	θ = 3.0–28.4°
b = 14.6915 (19) Å	µ = 0.29 mm⁻¹
c = 15.398 (3) Å	T = 180 K
V = 1471.4 (4) Å³	Needle, red
Z = 4	0.25 × 0.04 × 0.03 mm
F(000) = 720

Data collection top

Agilent Xcalibur (Sapphire1) diffractometer	3369 independent reflections
Radiation source: fine-focus sealed tube	1695 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
Detector resolution: 8.2632 pixels mm^-1	θ_max = 28.5°, θ_min = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −19→19
T_min = 0.685, T_max = 1.000	l = −19→19
9582 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0494P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
3369 reflections	Δρ_max = 0.26 e Å⁻³
218 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1362 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (13)

Crystal data top

C₁₆H₁₃N₂O⁺·ClO₄⁻	V = 1471.4 (4) Å³
M_r = 348.73	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.5043 (9) Å	µ = 0.29 mm⁻¹
b = 14.6915 (19) Å	T = 180 K
c = 15.398 (3) Å	0.25 × 0.04 × 0.03 mm

Data collection top

Agilent Xcalibur (Sapphire1) diffractometer	3369 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1695 reflections with I > 2σ(I)
T_min = 0.685, T_max = 1.000	R_int = 0.069
9582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.127	Δρ_max = 0.26 e Å⁻³
S = 0.92	Δρ_min = −0.28 e Å⁻³
3369 reflections	Absolute structure: Flack (1983), 1362 Friedel pairs
218 parameters	Absolute structure parameter: 0.43 (13)
0 restraints

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
Cl1	0.26988 (16)	0.25979 (7)	0.14441 (7)	0.0420 (3)
O1	0.3025 (4)	0.31465 (18)	0.63157 (19)	0.0404 (7)
H1	0.3022	0.3556	0.5954	0.061*
O13	0.3797 (5)	0.2618 (2)	0.0636 (2)	0.0567 (9)
O12	0.2121 (6)	0.1681 (2)	0.1622 (2)	0.0702 (10)
N1	0.2985 (5)	0.3865 (2)	0.4812 (2)	0.0283 (9)
O11	0.4044 (5)	0.2891 (2)	0.2118 (2)	0.0647 (10)
C17	0.2947 (6)	0.1364 (2)	0.4624 (3)	0.0271 (10)
C8	0.2991 (5)	0.2266 (2)	0.5012 (2)	0.0267 (9)
C9	0.3004 (5)	0.2340 (3)	0.5911 (3)	0.0297 (10)
C16	0.2929 (5)	0.1213 (3)	0.3737 (3)	0.0357 (10)
H16	0.2964	0.1707	0.3359	0.043*
C10	0.2994 (6)	0.1562 (3)	0.6438 (3)	0.0366 (10)
H10	0.3015	0.1627	0.7039	0.044*
C12	0.2913 (6)	0.0598 (2)	0.5180 (3)	0.0293 (9)
N5	0.2590 (6)	0.6228 (2)	0.4274 (3)	0.0455 (10)
H5	0.2496	0.6728	0.4562	0.055*
C1	0.2895 (6)	0.4649 (2)	0.4284 (3)	0.0302 (10)
C7	0.2958 (6)	0.3064 (2)	0.4483 (3)	0.0284 (9)
H7	0.2915	0.3	0.3882	0.034*
C11	0.2954 (6)	0.0720 (3)	0.6088 (3)	0.0373 (11)
H11	0.2954	0.0214	0.6451	0.045*
O14	0.0992 (5)	0.3161 (3)	0.1393 (3)	0.1075 (16)
C2	0.2884 (6)	0.4676 (3)	0.3384 (3)	0.0360 (11)
H2	0.2999	0.4138	0.307	0.043*
C13	0.2841 (7)	−0.0278 (3)	0.4825 (3)	0.0390 (11)
H13	0.2807	−0.0781	0.5192	0.047*
C3	0.2706 (7)	0.5487 (3)	0.2955 (3)	0.0405 (11)
H3	0.2684	0.5499	0.2351	0.049*
C4	0.2562 (7)	0.6270 (3)	0.3411 (3)	0.0443 (11)
H4	0.2445	0.6827	0.3127	0.053*
C15	0.2861 (7)	0.0350 (3)	0.3406 (3)	0.0455 (12)
H15	0.2843	0.0265	0.2807	0.055*
C6	0.2756 (7)	0.5459 (2)	0.4712 (3)	0.0374 (11)
H6	0.2778	0.5469	0.5316	0.045*
C14	0.2819 (7)	−0.0405 (3)	0.3954 (3)	0.0471 (12)
H14	0.2777	−0.099	0.3724	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0533 (6)	0.0401 (6)	0.0327 (6)	0.0063 (6)	0.0004 (6)	0.0032 (5)
O1	0.0468 (17)	0.0434 (16)	0.0311 (19)	−0.0026 (14)	0.0021 (18)	−0.0021 (14)
O13	0.078 (2)	0.059 (2)	0.033 (2)	0.0139 (19)	0.0153 (16)	0.0113 (18)
O12	0.106 (3)	0.0500 (19)	0.055 (3)	−0.036 (2)	0.000 (3)	0.0080 (16)
N1	0.027 (2)	0.0273 (17)	0.030 (2)	−0.0024 (16)	0.0026 (17)	−0.0030 (15)
O11	0.089 (2)	0.057 (2)	0.048 (3)	−0.0196 (19)	−0.006 (2)	−0.0124 (19)
C17	0.021 (2)	0.036 (2)	0.024 (3)	−0.0001 (19)	−0.003 (2)	−0.0003 (18)
C8	0.0181 (18)	0.034 (2)	0.028 (2)	0.0023 (18)	0.0019 (18)	0.0030 (18)
C9	0.023 (2)	0.036 (2)	0.030 (3)	−0.003 (2)	0.0009 (18)	−0.0020 (19)
C16	0.040 (2)	0.036 (2)	0.031 (3)	−0.005 (2)	0.004 (2)	0.0080 (18)
C10	0.033 (2)	0.055 (3)	0.022 (2)	−0.001 (2)	0.001 (2)	0.009 (2)
C12	0.023 (2)	0.030 (2)	0.034 (3)	−0.0001 (19)	0.001 (2)	0.0113 (18)
N5	0.056 (3)	0.0278 (19)	0.052 (3)	−0.005 (2)	0.006 (2)	−0.0102 (17)
C1	0.031 (2)	0.025 (2)	0.035 (3)	−0.004 (2)	0.003 (2)	−0.0012 (18)
C7	0.023 (2)	0.033 (2)	0.029 (2)	−0.0020 (19)	0.004 (2)	0.0023 (19)
C11	0.038 (2)	0.039 (2)	0.034 (3)	0.006 (2)	0.003 (2)	0.012 (2)
O14	0.104 (3)	0.128 (3)	0.091 (4)	0.078 (3)	0.039 (3)	0.043 (3)
C2	0.046 (3)	0.031 (2)	0.031 (3)	0.004 (2)	0.008 (2)	0.0033 (19)
C13	0.039 (3)	0.032 (2)	0.047 (3)	−0.003 (2)	0.004 (3)	0.009 (2)
C3	0.050 (3)	0.034 (2)	0.037 (3)	0.002 (3)	0.003 (3)	0.007 (2)
C4	0.049 (3)	0.032 (2)	0.051 (4)	0.001 (2)	0.006 (3)	0.010 (2)
C15	0.060 (3)	0.038 (3)	0.038 (3)	−0.002 (3)	0.002 (3)	−0.008 (2)
C6	0.041 (3)	0.027 (2)	0.044 (3)	−0.002 (2)	0.003 (3)	0.0008 (19)
C14	0.054 (3)	0.032 (2)	0.055 (3)	−0.005 (3)	0.005 (3)	0.000 (2)

Geometric parameters (Å, º) top

Cl1—O14	1.387 (3)	C12—C11	1.411 (5)
Cl1—O11	1.424 (3)	N5—C6	1.321 (5)
Cl1—O12	1.425 (3)	N5—C4	1.331 (5)
Cl1—O13	1.436 (3)	N5—H5	0.86
O1—C9	1.339 (4)	C1—C6	1.363 (5)
O1—H1	0.82	C1—C2	1.386 (5)
N1—C7	1.282 (4)	C7—H7	0.93
N1—C1	1.411 (5)	C11—H11	0.93
C17—C16	1.384 (6)	C2—C3	1.367 (5)
C17—C12	1.414 (5)	C2—H2	0.93
C17—C8	1.455 (5)	C13—C14	1.353 (6)
C8—C9	1.388 (5)	C13—H13	0.93
C8—C7	1.428 (5)	C3—C4	1.351 (5)
C9—C10	1.402 (5)	C3—H3	0.93
C16—C15	1.367 (5)	C4—H4	0.93
C16—H16	0.93	C15—C14	1.394 (5)
C10—C11	1.349 (5)	C15—H15	0.93
C10—H10	0.93	C6—H6	0.93
C12—C13	1.399 (5)	C14—H14	0.93

O14—Cl1—O11	110.6 (3)	C6—C1—N1	115.9 (4)
O14—Cl1—O12	111.3 (3)	C2—C1—N1	126.8 (3)
O11—Cl1—O12	107.9 (2)	N1—C7—C8	121.9 (4)
O14—Cl1—O13	109.7 (2)	N1—C7—H7	119.1
O11—Cl1—O13	108.6 (2)	C8—C7—H7	119.1
O12—Cl1—O13	108.5 (2)	C10—C11—C12	120.9 (4)
C9—O1—H1	109.5	C10—C11—H11	119.6
C7—N1—C1	121.4 (4)	C12—C11—H11	119.6
C16—C17—C12	118.0 (4)	C3—C2—C1	120.6 (4)
C16—C17—C8	123.5 (4)	C3—C2—H2	119.7
C12—C17—C8	118.5 (4)	C1—C2—H2	119.7
C9—C8—C7	120.3 (4)	C14—C13—C12	120.9 (4)
C9—C8—C17	118.8 (3)	C14—C13—H13	119.5
C7—C8—C17	120.9 (4)	C12—C13—H13	119.5
O1—C9—C8	122.2 (3)	C4—C3—C2	119.8 (4)
O1—C9—C10	116.9 (4)	C4—C3—H3	120.1
C8—C9—C10	120.9 (4)	C2—C3—H3	120.1
C15—C16—C17	121.1 (4)	N5—C4—C3	118.6 (4)
C15—C16—H16	119.4	N5—C4—H4	120.7
C17—C16—H16	119.4	C3—C4—H4	120.7
C11—C10—C9	121.1 (4)	C16—C15—C14	120.8 (4)
C11—C10—H10	119.4	C16—C15—H15	119.6
C9—C10—H10	119.4	C14—C15—H15	119.6
C13—C12—C11	120.4 (4)	N5—C6—C1	120.4 (4)
C13—C12—C17	119.7 (4)	N5—C6—H6	119.8
C11—C12—C17	119.9 (4)	C1—C6—H6	119.8
C6—N5—C4	123.4 (4)	C13—C14—C15	119.3 (4)
C6—N5—H5	118.3	C13—C14—H14	120.3
C4—N5—H5	118.3	C15—C14—H14	120.3
C6—C1—C2	117.3 (4)

C16—C17—C8—C9	179.9 (4)	C9—C8—C7—N1	1.6 (6)
C12—C17—C8—C9	0.2 (5)	C17—C8—C7—N1	179.7 (3)
C16—C17—C8—C7	1.8 (6)	C9—C10—C11—C12	−0.2 (6)
C12—C17—C8—C7	−177.9 (4)	C13—C12—C11—C10	−179.0 (4)
C7—C8—C9—O1	−1.3 (5)	C17—C12—C11—C10	1.0 (6)
C17—C8—C9—O1	−179.4 (3)	C6—C1—C2—C3	−1.0 (7)
C7—C8—C9—C10	178.7 (4)	N1—C1—C2—C3	177.3 (4)
C17—C8—C9—C10	0.6 (5)	C11—C12—C13—C14	−179.4 (4)
C12—C17—C16—C15	0.6 (6)	C17—C12—C13—C14	0.5 (6)
C8—C17—C16—C15	−179.2 (4)	C1—C2—C3—C4	0.7 (7)
O1—C9—C10—C11	179.4 (3)	C6—N5—C4—C3	0.1 (8)
C8—C9—C10—C11	−0.6 (6)	C2—C3—C4—N5	−0.2 (7)
C16—C17—C12—C13	−0.7 (6)	C17—C16—C15—C14	−0.3 (6)
C8—C17—C12—C13	179.1 (3)	C4—N5—C6—C1	−0.5 (7)
C16—C17—C12—C11	179.3 (4)	C2—C1—C6—N5	0.9 (7)
C8—C17—C12—C11	−1.0 (6)	N1—C1—C6—N5	−177.6 (4)
C7—N1—C1—C6	174.5 (4)	C12—C13—C14—C15	−0.3 (7)
C7—N1—C1—C2	−3.8 (7)	C16—C15—C14—C13	0.2 (7)
C1—N1—C7—C8	−178.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.545 (4)	147
N5—H5···O13ⁱ	0.86	2.09	2.844 (5)	146
C2—H2···O11	0.93	2.44	3.354 (5)	166
C3—H3···O1ⁱⁱ	0.93	2.59	3.260 (5)	129
C13—H13···O12ⁱⁱⁱ	0.93	2.57	3.451 (6)	158

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.545 (4)	147
N5—H5···O13ⁱ	0.86	2.09	2.844 (5)	146
C2—H2···O11	0.93	2.44	3.354 (5)	166
C3—H3···O1ⁱⁱ	0.93	2.59	3.260 (5)	129
C13—H13···O12ⁱⁱⁱ	0.93	2.57	3.451 (6)	158

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

Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, Algeria, and the Laboratoire de Chimie de Coordination Toulouse, France. Thanks are due to the Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie (via the PNR project) for financial support.

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