1-[(Z)-(5-Methyl-2-pyrid­yl)iminiometh­yl]-2-naphtholate

Liu, X.-Y.; Fan, Y.-H.; Wang, Q.; Bi, C.-F.; Wang, Y.-F.

doi:10.1107/S1600536810000346

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o309

https://doi.org/10.1107/S1600536810000346

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1-[(Z)-(5-Methyl-2-pyridyl)iminiomethyl]-2-naphtholate

Xin-Yu Liu,^a Yu-Hua Fan,^a ^* Qiang Wang,^a Cai-Feng Bi ^a and Yu-Fang Wang ^a

^aKey Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
^*Correspondence e-mail: fanyuhua301@163.com

(Received 28 December 2009; accepted 5 January 2010; online 9 January 2010)

In the zwitterionic title compound, C₁₇H₁₄N₂O, the dihedral angle between the naphthalene and pyridine ring systems is 3.56 (9)° and an intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by C—H⋯O interactions.

Related literature

For a related structure, see: Eltayeb et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₄N₂O
M_r = 262.30
Monoclinic, P 2₁
a = 4.8703 (2) Å
b = 9.5525 (5) Å
c = 14.0804 (6) Å
β = 98.353 (2)°
V = 648.12 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.47 × 0.10 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.961, T_max = 0.992
6930 measured reflections
1660 independent reflections
1321 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 0.98
1660 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.89	2.571 (3)	135
C3—H3⋯O1ⁱ	0.93	2.46	3.346 (3)	159
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810000346/hb5298sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000346/hb5298Isup2.hkl

checkCIF report

Comment top

One similar compound as 1-{2-[(2-hydroxy-1-naphthyl)methyleneamino] phenyliminiomethyl}-2-naphtholate methanol hemisolvate has been synthesized and characterized by X-ray diffraction (Eltayeb et al., 2007). We now report on the title compound, (I), whose structure was determined by X-ray diffraction (Fig. 1).

This compound, which has a non-planar molecular structure, contains two aromatic rings linked through a imine group. The dihedral angle between the two aromatic rings C2—C3—C4—C5—N1—C6 and C8—C9—C14—C15—C16—C17 is 3.46(0.16)°. Intramolecular N—H···O hydrogen bonds are observed in the molecular structure, similar to those reported structure (Eltayeb et al., 2007). The molecules is formed a one-dimensional zigzag chain through intermolecular C—H···O hydrogen bonds, which make the molecule more stabile.

As seen in Fig. 2, the molecules are linked into a one-dimensional chain by intermolecular C—H···O hydrogen bonds (Table 2).

Related literature top

For a related structure, see: Eltayeb et al. (2007).

Experimental top

2-Hydroxy-1-naphthaldehyde (1 mmol, 172.2 mg) were added with stirring to anhydrous ethanol (30 ml) to make a solution. It was slowly dropped into the anhydrous ethanol solution (15 ml) containing (1 mmol, 108.1 mg) 5-methylpyridin-2-amine at 339 K and mixture was stirred at 339 K for 4 h, a mass of deep yellow grain was separated out. The product was collected by filtration and washed several times with anhydrous ethanol and dried under vacuum. Yellow needles of (I) were obtained by slow evaporation at room temperature from anhydrous ethanol solution after 4 days.

Structure description top

As seen in Fig. 2, the molecules are linked into a one-dimensional chain by intermolecular C—H···O hydrogen bonds (Table 2).

For a related structure, see: Eltayeb et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I), viewed approximately along the a axis.

1-[(Z)-(5-Methyl-2-pyridyl)iminiomethyl]-2-naphtholate top

Crystal data top

C₁₇H₁₄N₂O	F(000) = 276
M_r = 262.30	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1877 reflections
a = 4.8703 (2) Å	θ = 2.6–25.6°
b = 9.5525 (5) Å	µ = 0.09 mm⁻¹
c = 14.0804 (6) Å	T = 296 K
β = 98.353 (2)°	Needle, yellow
V = 648.12 (5) Å³	0.47 × 0.10 × 0.09 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	1660 independent reflections
Radiation source: fine-focus sealed tube	1321 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 28.1°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
T_min = 0.961, T_max = 0.992	k = −12→11
6930 measured reflections	l = −18→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.062P)² + 0.0757P] where P = (F_o² + 2F_c²)/3
1660 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O	V = 648.12 (5) Å³
M_r = 262.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.8703 (2) Å	µ = 0.09 mm⁻¹
b = 9.5525 (5) Å	T = 296 K
c = 14.0804 (6) Å	0.47 × 0.10 × 0.09 mm
β = 98.353 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1660 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1321 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.992	R_int = 0.029
6930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.109	H-atom parameters constrained
S = 0.98	Δρ_max = 0.18 e Å⁻³
1660 reflections	Δρ_min = −0.15 e Å⁻³
182 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
C1	−0.5458 (5)	−0.0508 (3)	0.8827 (2)	0.0561 (6)
H1A	−0.6558	−0.0735	0.8224	0.084*
H1B	−0.6646	−0.0178	0.9266	0.084*
H1C	−0.4484	−0.1328	0.9086	0.084*
C2	−0.3401 (5)	0.0616 (2)	0.86752 (16)	0.0431 (5)
C3	−0.2411 (5)	0.1558 (3)	0.93834 (17)	0.0518 (6)
H3	−0.3011	0.1508	0.9980	0.062*
C4	−0.0533 (5)	0.2576 (3)	0.92116 (16)	0.0492 (6)
H4	0.0127	0.3223	0.9683	0.059*
C5	0.0341 (4)	0.2610 (2)	0.83229 (15)	0.0382 (5)
C6	−0.2414 (5)	0.0762 (3)	0.78108 (16)	0.0478 (6)
H6	−0.3082	0.0143	0.7322	0.057*
C7	0.3255 (4)	0.3752 (2)	0.73144 (15)	0.0398 (5)
H7	0.2584	0.3151	0.6815	0.048*
C8	0.5254 (4)	0.4749 (2)	0.71574 (15)	0.0383 (5)
C9	0.6227 (4)	0.4846 (2)	0.62325 (15)	0.0371 (5)
C10	0.5226 (5)	0.3996 (3)	0.54463 (16)	0.0468 (6)
H10	0.3905	0.3315	0.5518	0.056*
C11	0.6141 (5)	0.4140 (3)	0.45734 (16)	0.0501 (6)
H11	0.5423	0.3566	0.4064	0.060*
C12	0.8133 (5)	0.5138 (3)	0.44477 (17)	0.0525 (6)
H12	0.8743	0.5238	0.3855	0.063*
C13	0.9182 (5)	0.5968 (3)	0.51987 (18)	0.0510 (6)
H13	1.0539	0.6623	0.5116	0.061*
C14	0.8257 (4)	0.5857 (2)	0.60997 (16)	0.0413 (5)
C15	0.9323 (5)	0.6740 (3)	0.68904 (18)	0.0499 (6)
H15	1.0677	0.7395	0.6804	0.060*
C16	0.8457 (5)	0.6663 (3)	0.77458 (18)	0.0484 (6)
H16	0.9224	0.7259	0.8236	0.058*
C17	0.6352 (5)	0.5673 (2)	0.79247 (16)	0.0430 (5)
N1	−0.0571 (4)	0.1724 (2)	0.76194 (13)	0.0462 (5)
N2	0.2284 (4)	0.3625 (2)	0.81358 (13)	0.0424 (4)
H2	0.2877	0.4203	0.8588	0.051*
O1	0.5562 (4)	0.5643 (2)	0.87507 (11)	0.0567 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0517 (14)	0.0467 (15)	0.0725 (16)	−0.0048 (12)	0.0176 (12)	0.0080 (13)
C2	0.0391 (10)	0.0397 (12)	0.0520 (12)	0.0037 (10)	0.0115 (9)	0.0067 (11)
C3	0.0604 (14)	0.0536 (15)	0.0459 (12)	−0.0031 (13)	0.0230 (11)	0.0044 (12)
C4	0.0581 (14)	0.0484 (14)	0.0438 (12)	−0.0078 (12)	0.0163 (10)	−0.0060 (11)
C5	0.0403 (10)	0.0341 (11)	0.0416 (11)	0.0036 (9)	0.0108 (8)	0.0026 (9)
C6	0.0525 (13)	0.0435 (13)	0.0478 (12)	−0.0049 (11)	0.0081 (10)	−0.0027 (11)
C7	0.0436 (11)	0.0356 (11)	0.0418 (11)	0.0025 (9)	0.0116 (8)	0.0036 (9)
C8	0.0411 (10)	0.0322 (11)	0.0429 (11)	0.0033 (9)	0.0106 (8)	0.0024 (9)
C9	0.0370 (10)	0.0337 (11)	0.0421 (10)	0.0038 (9)	0.0103 (8)	0.0058 (9)
C10	0.0496 (13)	0.0447 (14)	0.0481 (12)	−0.0016 (11)	0.0136 (10)	0.0000 (11)
C11	0.0555 (14)	0.0529 (15)	0.0437 (12)	0.0054 (12)	0.0135 (10)	−0.0005 (11)
C12	0.0590 (14)	0.0553 (15)	0.0475 (13)	0.0092 (12)	0.0225 (10)	0.0091 (11)
C13	0.0504 (13)	0.0447 (14)	0.0615 (15)	0.0012 (11)	0.0203 (11)	0.0108 (12)
C14	0.0404 (11)	0.0356 (12)	0.0493 (12)	0.0033 (10)	0.0113 (9)	0.0055 (10)
C15	0.0486 (12)	0.0385 (13)	0.0645 (14)	−0.0057 (11)	0.0145 (10)	0.0025 (12)
C16	0.0508 (13)	0.0365 (12)	0.0582 (14)	−0.0035 (11)	0.0086 (10)	−0.0055 (11)
C17	0.0492 (12)	0.0356 (12)	0.0460 (12)	0.0033 (10)	0.0125 (9)	0.0016 (10)
N1	0.0536 (11)	0.0441 (11)	0.0430 (10)	−0.0029 (10)	0.0146 (8)	−0.0014 (9)
N2	0.0497 (11)	0.0370 (10)	0.0425 (9)	−0.0017 (9)	0.0134 (8)	−0.0010 (8)
O1	0.0721 (11)	0.0548 (11)	0.0463 (9)	−0.0073 (10)	0.0187 (8)	−0.0083 (8)

Geometric parameters (Å, º) top

C1—C2	1.504 (3)	C8—C9	1.452 (3)
C1—H1A	0.9600	C9—C10	1.402 (3)
C1—H1B	0.9600	C9—C14	1.413 (3)
C1—H1C	0.9600	C10—C11	1.374 (3)
C2—C3	1.377 (4)	C10—H10	0.9300
C2—C6	1.379 (3)	C11—C12	1.390 (4)
C3—C4	1.380 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.360 (4)
C4—C5	1.379 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.410 (3)
C5—N1	1.329 (3)	C13—H13	0.9300
C5—N2	1.407 (3)	C14—C15	1.433 (3)
C6—N1	1.339 (3)	C15—C16	1.335 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—N2	1.317 (3)	C16—C17	1.444 (3)
C7—C8	1.402 (3)	C16—H16	0.9300
C7—H7	0.9300	C17—O1	1.277 (3)
C8—C17	1.436 (3)	N2—H2	0.8600

C2—C1—H1A	109.5	C14—C9—C8	119.20 (19)
C2—C1—H1B	109.5	C11—C10—C9	121.8 (2)
H1A—C1—H1B	109.5	C11—C10—H10	119.1
C2—C1—H1C	109.5	C9—C10—H10	119.1
H1A—C1—H1C	109.5	C10—C11—C12	120.4 (2)
H1B—C1—H1C	109.5	C10—C11—H11	119.8
C3—C2—C6	116.3 (2)	C12—C11—H11	119.8
C3—C2—C1	122.3 (2)	C13—C12—C11	119.4 (2)
C6—C2—C1	121.5 (2)	C13—C12—H12	120.3
C2—C3—C4	120.3 (2)	C11—C12—H12	120.3
C2—C3—H3	119.8	C12—C13—C14	121.5 (2)
C4—C3—H3	119.8	C12—C13—H13	119.3
C5—C4—C3	118.4 (2)	C14—C13—H13	119.3
C5—C4—H4	120.8	C13—C14—C9	119.4 (2)
C3—C4—H4	120.8	C13—C14—C15	121.8 (2)
N1—C5—C4	123.2 (2)	C9—C14—C15	118.72 (19)
N1—C5—N2	117.42 (18)	C16—C15—C14	122.9 (2)
C4—C5—N2	119.4 (2)	C16—C15—H15	118.6
N1—C6—C2	125.2 (2)	C14—C15—H15	118.6
N1—C6—H6	117.4	C15—C16—C17	121.3 (2)
C2—C6—H6	117.4	C15—C16—H16	119.4
N2—C7—C8	123.2 (2)	C17—C16—H16	119.4
N2—C7—H7	118.4	O1—C17—C8	122.9 (2)
C8—C7—H7	118.4	O1—C17—C16	119.3 (2)
C7—C8—C17	119.32 (18)	C8—C17—C16	117.86 (19)
C7—C8—C9	120.61 (19)	C5—N1—C6	116.61 (19)
C17—C8—C9	120.07 (19)	C7—N2—C5	124.41 (19)
C10—C9—C14	117.45 (19)	C7—N2—H2	117.8
C10—C9—C8	123.34 (19)	C5—N2—H2	117.8

C6—C2—C3—C4	−0.1 (4)	C10—C9—C14—C13	0.0 (3)
C1—C2—C3—C4	−179.7 (2)	C8—C9—C14—C13	−179.1 (2)
C2—C3—C4—C5	−0.8 (4)	C10—C9—C14—C15	−179.9 (2)
C3—C4—C5—N1	1.1 (4)	C8—C9—C14—C15	1.0 (3)
C3—C4—C5—N2	−179.1 (2)	C13—C14—C15—C16	179.2 (2)
C3—C2—C6—N1	0.9 (4)	C9—C14—C15—C16	−0.9 (4)
C1—C2—C6—N1	−179.5 (2)	C14—C15—C16—C17	−0.3 (4)
N2—C7—C8—C17	1.0 (3)	C7—C8—C17—O1	−1.0 (3)
N2—C7—C8—C9	−179.45 (19)	C9—C8—C17—O1	179.5 (2)
C7—C8—C9—C10	1.4 (3)	C7—C8—C17—C16	178.5 (2)
C17—C8—C9—C10	−179.1 (2)	C9—C8—C17—C16	−1.1 (3)
C7—C8—C9—C14	−179.55 (19)	C15—C16—C17—O1	−179.3 (2)
C17—C8—C9—C14	0.0 (3)	C15—C16—C17—C8	1.2 (3)
C14—C9—C10—C11	−0.8 (3)	C4—C5—N1—C6	−0.3 (3)
C8—C9—C10—C11	178.3 (2)	N2—C5—N1—C6	179.8 (2)
C9—C10—C11—C12	0.6 (4)	C2—C6—N1—C5	−0.7 (3)
C10—C11—C12—C13	0.4 (4)	C8—C7—N2—C5	−178.1 (2)
C11—C12—C13—C14	−1.2 (4)	N1—C5—N2—C7	−0.1 (3)
C12—C13—C14—C9	1.0 (3)	C4—C5—N2—C7	−180.0 (2)
C12—C13—C14—C15	−179.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.89	2.571 (3)	135
C3—H3···O1ⁱ	0.93	2.46	3.346 (3)	159

Symmetry code: (i) −x, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O
M_r	262.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	4.8703 (2), 9.5525 (5), 14.0804 (6)
β (°)	98.353 (2)
V (Å³)	648.12 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.47 × 0.10 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.961, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	6930, 1660, 1321
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 0.98
No. of reflections	1660
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.89	2.571 (3)	135
C3—H3···O1ⁱ	0.93	2.46	3.346 (3)	159

Symmetry code: (i) −x, y−1/2, −z+2.

Acknowledgements

The authors acknowledge the National Science Foundation of China for its financial support for this project (grant No. 20971115).

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, o117–o119. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar