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

Abstract

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,

• a = 4.8703 (2) Å

• b = 9.5525 (5) Å

• c = 14.0804 (6) Å

• β = 98.353 (2)°

• V = 648.12 (5) ų

• 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[F ² > 2σ(F ²)] = 0.038

• wR(F ²) = 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

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.

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. All H-atoms were positioned geometrically (C—H = 0.93–0.96Å, N—H = 0.86Å) and refined as riding with U_iso(H) =1.2U_eq(carrier).

Figures

Fig. 1.

The structure of (I) showing 30% probability displacement ellipsoids.

Fig. 2.

The crystal packing of (I), viewed approximately along the a axis.

Crystal data

C17H14N2O	F(000) = 276
Mr = 262.30	Dx = 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

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

Refinement

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(Fo2) + (0.062P)2 + 0.0757P] where P = (Fo2 + 2Fc2)/3
1660 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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 codes: (i) −x, y−1/2, −z+2.