1-[(2-Anilinoeth-yl)iminiometh-yl]-2-naph-thol-ate.

The title Schiff base compound, C(19)H(18)N(2)O, was prepared by the reaction of equimolar quanti-ties of 2-hydr-oxy-1-naphthaldehyde with N-phenyl-ethane-1,2-diamine in a methanol solution. The mol-ecule adopts a zwitterionic conformation with the naphthyl OH group deprotonated and the imine N atom protonated. An intra-molecular 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, mol-ecules are linked through inter-molecular 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 = 290.35

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.06

1753 reflections

202 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019096/sj2625sup1.cif

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

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

C19H18N2O	F(000) = 616
Mr = 290.35	Dx = 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

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

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(Fo2) + (0.0531P)2 + 0.1092P] where P = (Fo2 + 2Fc2)/3
1753 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.18 e Å−3
3 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .