1-[(2-Anilinoeth­yl)iminiometh­yl]-2-naph­thol­ate

Hao, Y.-M.

doi:10.1107/S1600536809019096

organic compounds

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Volume 65| Part 6| June 2009| Page o1400

doi:10.1107/S1600536809019096

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1-[(2-Anilinoethyl)iminiomethyl]-2-naphtholate

Yu-Mei Hao ^a ^*

^aDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: jyxygzb@163.com

(Received 18 May 2009; accepted 20 May 2009; online 23 May 2009)

The title Schiff base compound, C₁₉H₁₈N₂O, was prepared by the reaction of equimolar quantities of 2-hydroxy-1-naphthaldehyde with N-phenylethane-1,2-diamine in a methanol solution. The molecule adopts a zwitterionic conformation with the naphthyl OH group deprotonated and the imine N atom protonated. An intramolecular N—H⋯O hydrogen bond forms between them. The dihedral angle between the benzene ring and the naphthyl system is 86.9 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

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 Schiff base coordination chemistry, see: Ali et al. (2008 ); Kargar et al. (2009 ); Yeap et al. (2009 ). For related structures, see: Fun et al. (2009 ); Nadeem et al. (2009 ); Eltayeb et al. (2008 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₈N₂O
M_r = 290.35
Monoclinic, C c
a = 27.511 (3) Å
b = 6.845 (2) Å
c = 8.543 (2) Å
β = 104.263 (2)°
V = 1559.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.986
4485 measured reflections
1753 independent reflections
1312 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.06
1753 reflections
202 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.907 (10)	1.84 (3)	2.582 (3)	137 (3)
N2—H2⋯O1ⁱ	0.86	2.43	3.043 (3)	129
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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 global, I. DOI: 10.1107/S1600536809019096/sj2625sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019096/sj2625Isup2.hkl

checkCIF report

Comment top

Schiff base compounds are an important class of materials used in the pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). They are also used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of several Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). In this paper, the new Schiff base title compound, (I), Fig. 1, is reported.

In (I), the H atom of the phenol group is transferred to the imine N atom, forming an intramolecular N–H···O hydrogen bond (Table 1). The dihedral angle between the benzene ring and the naphthyl ring is 86.9 (2)°. All the bond lengths are within normal values (Allen et al., 1987). In the crystal structure of the compound, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

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 Schiff base coordination chemistry, see: Ali et al. (2008); Kargar et al. (2009); Yeap et al. (2009). For related structures, see: Fun et al. (2009); Nadeem et al. (2009); Eltayeb et al. (2008). For reference structural data, see: Allen et al. (1987).

Experimental top

2-Hydroxy-1-naphthylaldehyde (0.1 mmol, 17.2 mg) and N-phenylethane-1,2-diamine (0.1 mmol, 13.6 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear orange solution. Yellow block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 molecular structure of (I) with 30% probability ellipsoids. The intramolecular N–H···O hydrogen bond is shown as a dashed line.
	Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.

1-[(2-Anilinoethyl)iminiomethyl]-2-naphtholate top

Crystal data top

C₁₉H₁₈N₂O	F(000) = 616
M_r = 290.35	D_x = 1.237 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1258 reflections
a = 27.511 (3) Å	θ = 2.5–24.5°
b = 6.845 (2) Å	µ = 0.08 mm⁻¹
c = 8.543 (2) Å	T = 298 K
β = 104.263 (2)°	Block, yellow
V = 1559.2 (6) Å³	0.23 × 0.21 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1753 independent reflections
Radiation source: fine-focus sealed tube	1312 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→35
T_min = 0.982, T_max = 0.986	k = −6→8
4485 measured reflections	l = −11→11

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) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0531P)² + 0.1092P] where P = (F_o² + 2F_c²)/3
1753 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.18 e Å⁻³
3 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₁₈N₂O	V = 1559.2 (6) Å³
M_r = 290.35	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 27.511 (3) Å	µ = 0.08 mm⁻¹
b = 6.845 (2) Å	T = 298 K
c = 8.543 (2) Å	0.23 × 0.21 × 0.18 mm
β = 104.263 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1753 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1312 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.986	R_int = 0.021
4485 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	3 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.18 e Å⁻³
1753 reflections	Δρ_min = −0.18 e Å⁻³
202 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.52924 (7)	0.9086 (3)	0.4162 (2)	0.0576 (5)
N1	0.53391 (8)	0.5581 (3)	0.5306 (3)	0.0497 (5)
N2	0.46277 (8)	0.2671 (3)	0.3271 (3)	0.0522 (6)
H2	0.4912	0.2202	0.3207	0.063*
C1	0.60256 (9)	0.7135 (4)	0.4543 (3)	0.0465 (6)
C2	0.57425 (10)	0.8886 (4)	0.4038 (3)	0.0491 (6)
C3	0.59731 (11)	1.0404 (4)	0.3330 (4)	0.0608 (7)
H3	0.5793	1.1537	0.2974	0.073*
C4	0.64475 (12)	1.0231 (5)	0.3167 (4)	0.0658 (8)
H4	0.6583	1.1247	0.2689	0.079*
C5	0.67481 (11)	0.8544 (5)	0.3702 (3)	0.0583 (7)
C6	0.72446 (13)	0.8429 (6)	0.3537 (5)	0.0791 (10)
H6	0.7374	0.9433	0.3027	0.095*
C7	0.75394 (13)	0.6840 (7)	0.4128 (5)	0.0908 (12)
H7	0.7868	0.6775	0.4031	0.109*
C8	0.73446 (14)	0.5358 (7)	0.4859 (6)	0.0953 (13)
H8	0.7546	0.4294	0.5269	0.114*
C9	0.68608 (12)	0.5403 (5)	0.5000 (5)	0.0748 (9)
H9	0.6738	0.4360	0.5487	0.090*
C10	0.65441 (10)	0.6995 (4)	0.4422 (3)	0.0541 (7)
C11	0.57962 (10)	0.5575 (4)	0.5134 (3)	0.0490 (6)
H11	0.5985	0.4445	0.5427	0.059*
C12	0.50873 (11)	0.3947 (4)	0.5875 (4)	0.0568 (7)
H12A	0.5046	0.4237	0.6945	0.068*
H12B	0.5293	0.2784	0.5948	0.068*
C13	0.45822 (10)	0.3570 (4)	0.4749 (4)	0.0540 (7)
H13A	0.4389	0.2724	0.5278	0.065*
H13B	0.4403	0.4796	0.4504	0.065*
C14	0.42170 (10)	0.2552 (4)	0.1944 (3)	0.0477 (6)
C15	0.42493 (12)	0.1449 (4)	0.0608 (4)	0.0590 (7)
H15	0.4542	0.0759	0.0627	0.071*
C16	0.38583 (14)	0.1359 (4)	−0.0735 (4)	0.0689 (9)
H16	0.3890	0.0605	−0.1609	0.083*
C17	0.34208 (13)	0.2356 (5)	−0.0821 (5)	0.0732 (9)
H17	0.3157	0.2291	−0.1742	0.088*
C18	0.33809 (12)	0.3459 (5)	0.0492 (4)	0.0687 (8)
H18	0.3088	0.4154	0.0454	0.082*
C19	0.37702 (11)	0.3545 (4)	0.1862 (4)	0.0579 (7)
H19	0.3734	0.4276	0.2743	0.070*
H1	0.5170 (12)	0.671 (3)	0.501 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0519 (11)	0.0450 (10)	0.0754 (13)	0.0099 (8)	0.0146 (9)	0.0058 (9)
N1	0.0534 (14)	0.0385 (12)	0.0542 (13)	0.0029 (9)	0.0075 (11)	0.0009 (9)
N2	0.0450 (12)	0.0432 (12)	0.0711 (15)	0.0038 (9)	0.0196 (11)	−0.0043 (10)
C1	0.0464 (14)	0.0426 (13)	0.0468 (13)	0.0018 (11)	0.0048 (11)	−0.0035 (11)
C2	0.0530 (16)	0.0412 (14)	0.0482 (15)	0.0029 (11)	0.0032 (12)	−0.0041 (11)
C3	0.0627 (18)	0.0502 (17)	0.0656 (19)	0.0018 (13)	0.0084 (15)	0.0088 (14)
C4	0.068 (2)	0.0579 (18)	0.0687 (19)	−0.0112 (14)	0.0112 (16)	0.0064 (15)
C5	0.0512 (15)	0.064 (2)	0.0569 (16)	−0.0055 (13)	0.0081 (13)	−0.0087 (13)
C6	0.058 (2)	0.092 (3)	0.088 (2)	−0.0136 (18)	0.0210 (18)	−0.009 (2)
C7	0.054 (2)	0.107 (3)	0.112 (3)	0.005 (2)	0.021 (2)	−0.014 (3)
C8	0.063 (2)	0.087 (3)	0.136 (4)	0.025 (2)	0.024 (2)	0.004 (3)
C9	0.0580 (19)	0.067 (2)	0.098 (2)	0.0130 (15)	0.0163 (18)	0.0022 (19)
C10	0.0495 (15)	0.0532 (16)	0.0548 (16)	0.0020 (12)	0.0039 (12)	−0.0087 (12)
C11	0.0533 (16)	0.0392 (14)	0.0500 (14)	0.0088 (11)	0.0041 (11)	−0.0025 (11)
C12	0.0704 (18)	0.0447 (14)	0.0568 (16)	0.0015 (13)	0.0184 (14)	0.0058 (13)
C13	0.0594 (16)	0.0397 (14)	0.0665 (17)	−0.0028 (12)	0.0226 (14)	−0.0025 (12)
C14	0.0474 (15)	0.0345 (12)	0.0659 (17)	−0.0024 (10)	0.0230 (14)	0.0004 (11)
C15	0.0647 (17)	0.0372 (13)	0.081 (2)	−0.0035 (12)	0.0301 (16)	−0.0078 (13)
C16	0.086 (2)	0.0496 (18)	0.074 (2)	−0.0129 (17)	0.0246 (19)	−0.0135 (15)
C17	0.074 (2)	0.0609 (19)	0.079 (2)	−0.0137 (17)	0.0080 (17)	0.0017 (17)
C18	0.0557 (18)	0.0620 (19)	0.087 (2)	0.0049 (15)	0.0152 (17)	0.0037 (17)
C19	0.0548 (16)	0.0503 (17)	0.0725 (19)	0.0072 (12)	0.0228 (14)	−0.0027 (13)

Geometric parameters (Å, º) top

O1—C2	1.276 (3)	C8—C9	1.366 (5)
N1—C11	1.302 (3)	C8—H8	0.9300
N1—C12	1.460 (3)	C9—C10	1.407 (4)
N1—H1	0.907 (10)	C9—H9	0.9300
N2—C14	1.392 (3)	C11—H11	0.9300
N2—C13	1.437 (3)	C12—C13	1.505 (4)
N2—H2	0.8600	C12—H12A	0.9700
C1—C11	1.397 (4)	C12—H12B	0.9700
C1—C2	1.436 (4)	C13—H13A	0.9700
C1—C10	1.459 (4)	C13—H13B	0.9700
C2—C3	1.427 (4)	C14—C15	1.389 (4)
C3—C4	1.351 (4)	C14—C19	1.391 (4)
C3—H3	0.9300	C15—C16	1.367 (5)
C4—C5	1.428 (5)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.370 (5)
C5—C6	1.409 (4)	C16—H16	0.9300
C5—C10	1.410 (4)	C17—C18	1.379 (5)
C6—C7	1.376 (6)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.379 (4)
C7—C8	1.368 (6)	C18—H18	0.9300
C7—H7	0.9300	C19—H19	0.9300

C11—N1—C12	125.9 (2)	C5—C10—C1	118.9 (2)
C11—N1—H1	114 (2)	N1—C11—C1	125.0 (2)
C12—N1—H1	120 (2)	N1—C11—H11	117.5
C14—N2—C13	120.8 (2)	C1—C11—H11	117.5
C14—N2—H2	119.6	N1—C12—C13	111.0 (2)
C13—N2—H2	119.6	N1—C12—H12A	109.4
C11—C1—C2	119.1 (2)	C13—C12—H12A	109.4
C11—C1—C10	120.8 (2)	N1—C12—H12B	109.4
C2—C1—C10	120.1 (2)	C13—C12—H12B	109.4
O1—C2—C3	119.9 (2)	H12A—C12—H12B	108.0
O1—C2—C1	122.0 (2)	N2—C13—C12	111.6 (2)
C3—C2—C1	118.0 (2)	N2—C13—H13A	109.3
C4—C3—C2	121.4 (3)	C12—C13—H13A	109.3
C4—C3—H3	119.3	N2—C13—H13B	109.3
C2—C3—H3	119.3	C12—C13—H13B	109.3
C3—C4—C5	122.4 (3)	H13A—C13—H13B	108.0
C3—C4—H4	118.8	C15—C14—C19	117.3 (3)
C5—C4—H4	118.8	C15—C14—N2	119.9 (2)
C6—C5—C10	120.1 (3)	C19—C14—N2	122.8 (2)
C6—C5—C4	120.8 (3)	C16—C15—C14	121.1 (3)
C10—C5—C4	119.1 (3)	C16—C15—H15	119.4
C7—C6—C5	120.4 (4)	C14—C15—H15	119.4
C7—C6—H6	119.8	C15—C16—C17	121.5 (3)
C5—C6—H6	119.8	C15—C16—H16	119.3
C8—C7—C6	119.5 (3)	C17—C16—H16	119.3
C8—C7—H7	120.3	C16—C17—C18	118.3 (3)
C6—C7—H7	120.3	C16—C17—H17	120.9
C9—C8—C7	121.5 (4)	C18—C17—H17	120.9
C9—C8—H8	119.2	C17—C18—C19	120.8 (3)
C7—C8—H8	119.2	C17—C18—H18	119.6
C8—C9—C10	121.3 (4)	C19—C18—H18	119.6
C8—C9—H9	119.4	C18—C19—C14	120.9 (3)
C10—C9—H9	119.4	C18—C19—H19	119.5
C9—C10—C5	117.2 (3)	C14—C19—H19	119.5
C9—C10—C1	123.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.91 (1)	1.84 (3)	2.582 (3)	137 (3)
N2—H2···O1ⁱ	0.86	2.43	3.043 (3)	129

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₂O
M_r	290.35
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	27.511 (3), 6.845 (2), 8.543 (2)
β (°)	104.263 (2)
V (Å³)	1559.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	4485, 1753, 1312
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.06
No. of reflections	1753
No. of parameters	202
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
N1—H1···O1	0.907 (10)	1.84 (3)	2.582 (3)	137 (3)
N2—H2···O1ⁱ	0.86	2.43	3.043 (3)	129.1

Symmetry code: (i) x, y−1, z.

References

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Volume 65| Part 6| June 2009| Page o1400

doi:10.1107/S1600536809019096

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