(E)-N-[(2-Eth­oxy­naphthalen-1-yl)methyl­idene]-2-ethyl­aniline

Kargılı, H.; Macit, M.; Alpaslan, G.; Kazak, C.; Erdönmez, A.

doi:10.1107/S1600536812043097

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3176

doi:10.1107/S1600536812043097

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(E)-N-[(2-Ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline

Hakan Kargılı,^a Mustafa Macit,^b Gökhan Alpaslan,^c ^* Canan Kazak ^a and Ahmet Erdönmez ^a

^aDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey, ^bDepartment of Chemistry, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey, and ^cDepartment of Medical Services, and Techniques, Vocational School of Health Services, Giresun University, TR-28200 Giresun, Turkey
^*Correspondence e-mail: gokhan.alpaslan@giresun.edu.tr

(Received 5 October 2012; accepted 16 October 2012; online 20 October 2012)

In the title compound, C₂₁H₂₁NO, the dihedral angle between the naphthalene ring system and the benzene ring is 64.61 (6)°. The molecular structure is stabilized by an intramolecular C—H⋯N hydrogen bond.

Related literature

For biological properties of Schiff bases, see: Lozier et al. (1975 ). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009 ); Yeap et al. (2009 ). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ). For a related structure, see: Vesek et al. (2012 ).

Experimental

Crystal data

C₂₁H₂₁NO
M_r = 303.39
Monoclinic, P 2₁ /c
a = 11.6011 (11) Å
b = 20.457 (3) Å
c = 7.4335 (7) Å
β = 101.303 (8)°
V = 1730.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.71 × 0.55 × 0.36 mm

Data collection

Stoe IPDS-II diffractometer
14212 measured reflections
3403 independent reflections
1769 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.211
S = 0.94
3403 reflections
209 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N1	0.93	2.32	2.961 (4)	126

Data collection: X-AREA (Stoe & Cie, 2002 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043097/fj2600sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043097/fj2600Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043097/fj2600Isup3.cml

checkCIF report

Comment top

Schiff bases often exhibit various biological activities and in many cases were shown to have antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al., 1975). Schiff bases have also been used as versatile ligands in coordination chemistry (Kargar et al., 2009; Yeap et al., 2009). In this paper, the structure of the title compound, is reported. An ORTEP-3 (Farrugia, 2012) plot of the molecule of (I) is shown in Fig.1. The geometric parameters in (I) are comparable with those in (E)-3-Chloro-N-[(2-ethoxynaphthalen -1-yl)methylidene]aniline (Vesek et al., 2012). The dihedral angle between the naphthalene ring and the benzene ring is 64.61 (6)°. The molecular structure is stabilized by a C9-H9···N1 intramolecular hydrogen bond which generates an S(6) ring motif (Bernstein et al., 1995).

Related literature top

For biological properties of Schiff bases, see: Lozier et al. (1975). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009); Yeap et al. (2009). For hydrogen-bonding motifs, see: Bernstein et al. (1995). For a related structure, see: Vesek et al. (2012).

Experimental top

The compound (E)-N-((2-ethoxynaphthalen-1-yl)methylene)-2-ethylaniline was prepared by refluxing a mixture of a solution containing 2-ethoxy-1-naphthaldehyde (20,0 mg, 0,1 mmol) in ethanol (20 ml) and a solution containing 2-ethylaniline (12,12 mg, 0,1 mmol) in ethanol (20 ml). The reaction mixture was stirred for 5 hour under reflux. Single crystals of the title compound for x-ray analysis were obtained by slow evaporation of an ethanol solution (Yield 62%; m.p.376-378 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability.

(E)-N-[(2-Ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline top

Crystal data top

C₂₁H₂₁NO	F(000) = 648
M_r = 303.39	D_x = 1.165 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10574 reflections
a = 11.6011 (11) Å	θ = 1.8–27.9°
b = 20.457 (3) Å	µ = 0.07 mm⁻¹
c = 7.4335 (7) Å	T = 296 K
β = 101.303 (8)°	Prism, yellow
V = 1730.0 (3) Å³	0.71 × 0.55 × 0.36 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	1769 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
Detector resolution: 6.67 pixels mm^-1	h = −14→14
ω scans	k = −25→25
14212 measured reflections	l = −9→9
3403 independent reflections

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.1288P)²] where P = (F_o² + 2F_c²)/3
3403 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.45 e Å⁻³
16 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₁H₂₁NO	V = 1730.0 (3) Å³
M_r = 303.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6011 (11) Å	µ = 0.07 mm⁻¹
b = 20.457 (3) Å	T = 296 K
c = 7.4335 (7) Å	0.71 × 0.55 × 0.36 mm
β = 101.303 (8)°

Data collection top

Stoe IPDS-II diffractometer	1769 reflections with I > 2σ(I)
14212 measured reflections	R_int = 0.055
3403 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	16 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 0.94	Δρ_max = 0.45 e Å⁻³
3403 reflections	Δρ_min = −0.31 e Å⁻³
209 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
C1	0.4025 (2)	0.19226 (13)	0.3272 (3)	0.0619 (7)
C2	0.3508 (2)	0.25280 (13)	0.2813 (4)	0.0664 (7)
C3	0.2305 (3)	0.25814 (17)	0.2024 (4)	0.0784 (8)
H3	0.1976	0.2989	0.1686	0.094*
C4	0.1635 (3)	0.20410 (18)	0.1760 (4)	0.0810 (9)
H4	0.0837	0.2085	0.1273	0.097*
C5	0.2097 (2)	0.14074 (15)	0.2197 (4)	0.0707 (8)
C6	0.1392 (3)	0.08513 (19)	0.1902 (5)	0.0905 (10)
H6	0.0597	0.0897	0.1395	0.109*
C7	0.1834 (3)	0.0246 (2)	0.2336 (5)	0.1001 (11)
H7	0.1349	−0.0120	0.2132	0.120*
C8	0.3027 (3)	0.01776 (16)	0.3093 (5)	0.0901 (9)
H8	0.3332	−0.0237	0.3402	0.108*
C9	0.3751 (3)	0.07046 (14)	0.3386 (4)	0.0753 (8)
H9	0.4544	0.0645	0.3880	0.090*
C10	0.3315 (2)	0.13437 (13)	0.2950 (4)	0.0620 (7)
C11	0.5272 (2)	0.19292 (13)	0.4136 (4)	0.0642 (7)
H11	0.5578	0.2324	0.4633	0.077*
C12	0.7140 (2)	0.15485 (13)	0.5261 (4)	0.0661 (7)
C13	0.7377 (3)	0.18615 (15)	0.6913 (4)	0.0808 (9)
H13	0.6761	0.2040	0.7386	0.097*
C14	0.8499 (3)	0.19186 (17)	0.7886 (5)	0.0958 (11)
H14	0.8640	0.2131	0.9015	0.115*
C15	0.9404 (3)	0.16685 (18)	0.7216 (5)	0.0938 (10)
H15	1.0170	0.1712	0.7871	0.113*
C16	0.9191 (3)	0.13519 (19)	0.5575 (5)	0.1005 (12)
H16	0.9819	0.1179	0.5124	0.121*
C17	0.8060 (3)	0.12796 (18)	0.4555 (5)	0.0971 (10)
C18	0.7839 (4)	0.0973 (4)	0.2575 (7)	0.184 (3)
H18A	0.7015	0.1018	0.2010	0.221*
H18B	0.8298	0.1208	0.1825	0.221*
C19	0.8162 (8)	0.0289 (3)	0.2652 (10)	0.226 (3)
H19A	0.8030	0.0113	0.1431	0.339*
H19B	0.7692	0.0055	0.3366	0.339*
H19C	0.8978	0.0245	0.3209	0.339*
C20	0.3711 (3)	0.36953 (14)	0.3110 (4)	0.0817 (9)
H20A	0.3133	0.3707	0.3892	0.098*
H20B	0.3326	0.3812	0.1873	0.098*
C21	0.4679 (4)	0.41565 (17)	0.3792 (6)	0.1107 (12)
H21A	0.4369	0.4591	0.3800	0.166*
H21B	0.5243	0.4142	0.3004	0.166*
H21C	0.5054	0.4036	0.5015	0.166*
N1	0.59740 (19)	0.14530 (11)	0.4274 (3)	0.0729 (7)
O1	0.42183 (17)	0.30550 (9)	0.3129 (3)	0.0820 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0527 (14)	0.0783 (18)	0.0563 (15)	0.0040 (12)	0.0148 (11)	0.0010 (12)
C2	0.0592 (15)	0.0801 (18)	0.0615 (16)	0.0058 (13)	0.0162 (12)	0.0046 (13)
C3	0.0663 (18)	0.095 (2)	0.0730 (19)	0.0177 (15)	0.0104 (14)	0.0069 (15)
C4	0.0559 (16)	0.112 (2)	0.071 (2)	0.0119 (16)	0.0036 (14)	−0.0018 (17)
C5	0.0571 (16)	0.096 (2)	0.0588 (17)	−0.0025 (14)	0.0121 (12)	−0.0122 (14)
C6	0.0628 (18)	0.116 (3)	0.091 (2)	−0.0098 (18)	0.0125 (15)	−0.018 (2)
C7	0.088 (2)	0.104 (3)	0.112 (3)	−0.029 (2)	0.029 (2)	−0.025 (2)
C8	0.084 (2)	0.080 (2)	0.111 (3)	−0.0078 (17)	0.0304 (18)	−0.0116 (18)
C9	0.0662 (17)	0.0798 (19)	0.082 (2)	0.0005 (15)	0.0195 (14)	−0.0035 (15)
C10	0.0566 (15)	0.0787 (18)	0.0532 (15)	0.0015 (12)	0.0166 (11)	−0.0037 (12)
C11	0.0578 (15)	0.0722 (16)	0.0633 (16)	−0.0008 (12)	0.0133 (12)	0.0009 (12)
C12	0.0543 (14)	0.0678 (16)	0.0740 (19)	−0.0001 (12)	0.0075 (12)	0.0007 (13)
C13	0.0674 (17)	0.088 (2)	0.084 (2)	0.0005 (14)	0.0091 (15)	−0.0120 (16)
C14	0.077 (2)	0.109 (3)	0.094 (2)	−0.0061 (18)	−0.0013 (18)	−0.0219 (19)
C15	0.0596 (18)	0.112 (3)	0.101 (3)	−0.0172 (17)	−0.0050 (17)	0.009 (2)
C16	0.0576 (18)	0.145 (3)	0.097 (3)	0.0103 (18)	0.0111 (17)	−0.006 (2)
C17	0.0582 (18)	0.129 (3)	0.101 (2)	0.0164 (18)	0.0087 (16)	−0.0085 (19)
C18	0.085 (3)	0.291 (5)	0.168 (4)	0.056 (4)	0.005 (3)	−0.116 (4)
C19	0.272 (7)	0.219 (5)	0.197 (6)	−0.055 (5)	0.071 (5)	−0.055 (5)
C20	0.097 (2)	0.079 (2)	0.0715 (19)	0.0159 (17)	0.0227 (16)	0.0117 (15)
C21	0.125 (3)	0.084 (2)	0.124 (3)	−0.006 (2)	0.027 (2)	−0.006 (2)
N1	0.0529 (12)	0.0801 (15)	0.0832 (17)	0.0061 (11)	0.0072 (11)	−0.0080 (12)
O1	0.0715 (12)	0.0713 (13)	0.1033 (16)	0.0058 (10)	0.0174 (11)	0.0105 (10)

Geometric parameters (Å, º) top

C1—C2	1.389 (4)	C12—N1	1.420 (3)
C1—C10	1.435 (4)	C13—C14	1.365 (4)
C1—C11	1.464 (3)	C13—H13	0.9300
C2—O1	1.349 (3)	C14—C15	1.348 (5)
C2—C3	1.408 (4)	C14—H14	0.9300
C3—C4	1.344 (4)	C15—C16	1.360 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.416 (4)	C16—C17	1.388 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.393 (4)	C17—C18	1.573 (5)
C5—C10	1.420 (4)	C18—C19	1.449 (7)
C6—C7	1.356 (5)	C18—H18A	0.9700
C6—H6	0.9300	C18—H18B	0.9700
C7—C8	1.395 (5)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C8—C9	1.357 (4)	C19—H19C	0.9600
C8—H8	0.9300	C20—O1	1.435 (3)
C9—C10	1.416 (4)	C20—C21	1.478 (5)
C9—H9	0.9300	C20—H20A	0.9700
C11—N1	1.261 (3)	C20—H20B	0.9700
C11—H11	0.9300	C21—H21A	0.9600
C12—C13	1.364 (4)	C21—H21B	0.9600
C12—C17	1.392 (4)	C21—H21C	0.9600

C2—C1—C10	119.3 (2)	C15—C14—C13	120.2 (3)
C2—C1—C11	116.2 (2)	C15—C14—H14	119.9
C10—C1—C11	124.5 (2)	C13—C14—H14	119.9
O1—C2—C1	116.7 (2)	C14—C15—C16	119.6 (3)
O1—C2—C3	122.2 (3)	C14—C15—H15	120.2
C1—C2—C3	121.1 (3)	C16—C15—H15	120.2
C4—C3—C2	119.7 (3)	C15—C16—C17	121.8 (3)
C4—C3—H3	120.2	C15—C16—H16	119.1
C2—C3—H3	120.2	C17—C16—H16	119.1
C3—C4—C5	122.5 (3)	C16—C17—C12	117.7 (3)
C3—C4—H4	118.7	C16—C17—C18	121.1 (3)
C5—C4—H4	118.7	C12—C17—C18	120.9 (3)
C6—C5—C4	121.8 (3)	C19—C18—C17	110.8 (5)
C6—C5—C10	119.7 (3)	C19—C18—H18A	109.5
C4—C5—C10	118.5 (3)	C17—C18—H18A	109.5
C7—C6—C5	121.7 (3)	C19—C18—H18B	109.5
C7—C6—H6	119.1	C17—C18—H18B	109.5
C5—C6—H6	119.1	H18A—C18—H18B	108.1
C6—C7—C8	119.1 (3)	C18—C19—H19A	109.5
C6—C7—H7	120.4	C18—C19—H19B	109.5
C8—C7—H7	120.4	H19A—C19—H19B	109.5
C9—C8—C7	121.3 (3)	C18—C19—H19C	109.5
C9—C8—H8	119.4	H19A—C19—H19C	109.5
C7—C8—H8	119.4	H19B—C19—H19C	109.5
C8—C9—C10	121.0 (3)	O1—C20—C21	107.3 (3)
C8—C9—H9	119.5	O1—C20—H20A	110.3
C10—C9—H9	119.5	C21—C20—H20A	110.3
C9—C10—C5	117.2 (2)	O1—C20—H20B	110.3
C9—C10—C1	123.8 (2)	C21—C20—H20B	110.3
C5—C10—C1	118.9 (2)	H20A—C20—H20B	108.5
N1—C11—C1	126.6 (3)	C20—C21—H21A	109.5
N1—C11—H11	116.7	C20—C21—H21B	109.5
C1—C11—H11	116.7	H21A—C21—H21B	109.5
C13—C12—C17	119.4 (3)	C20—C21—H21C	109.5
C13—C12—N1	122.2 (3)	H21A—C21—H21C	109.5
C17—C12—N1	118.3 (3)	H21B—C21—H21C	109.5
C12—C13—C14	121.4 (3)	C11—N1—C12	118.0 (2)
C12—C13—H13	119.3	C2—O1—C20	119.5 (2)
C14—C13—H13	119.3

C10—C1—C2—O1	−179.4 (2)	C11—C1—C10—C5	176.3 (2)
C11—C1—C2—O1	3.0 (4)	C2—C1—C11—N1	−162.3 (3)
C10—C1—C2—C3	−0.6 (4)	C10—C1—C11—N1	20.3 (4)
C11—C1—C2—C3	−178.2 (2)	C17—C12—C13—C14	0.2 (5)
O1—C2—C3—C4	−179.2 (3)	N1—C12—C13—C14	176.6 (3)
C1—C2—C3—C4	2.1 (4)	C12—C13—C14—C15	0.6 (5)
C2—C3—C4—C5	−1.9 (5)	C13—C14—C15—C16	−0.8 (6)
C3—C4—C5—C6	−179.5 (3)	C14—C15—C16—C17	0.3 (6)
C3—C4—C5—C10	0.3 (4)	C15—C16—C17—C12	0.5 (6)
C4—C5—C6—C7	−179.4 (3)	C15—C16—C17—C18	174.0 (5)
C10—C5—C6—C7	0.8 (5)	C13—C12—C17—C16	−0.7 (5)
C5—C6—C7—C8	−0.2 (6)	N1—C12—C17—C16	−177.2 (3)
C6—C7—C8—C9	−0.6 (6)	C13—C12—C17—C18	−174.2 (4)
C7—C8—C9—C10	0.7 (5)	N1—C12—C17—C18	9.3 (6)
C8—C9—C10—C5	0.0 (4)	C16—C17—C18—C19	67.1 (7)
C8—C9—C10—C1	178.2 (3)	C12—C17—C18—C19	−119.6 (5)
C6—C5—C10—C9	−0.7 (4)	C1—C11—N1—C12	−176.3 (3)
C4—C5—C10—C9	179.5 (3)	C13—C12—N1—C11	45.1 (4)
C6—C5—C10—C1	−179.0 (3)	C17—C12—N1—C11	−138.6 (3)
C4—C5—C10—C1	1.2 (4)	C1—C2—O1—C20	−165.1 (2)
C2—C1—C10—C9	−179.3 (3)	C3—C2—O1—C20	16.1 (4)
C11—C1—C10—C9	−1.9 (4)	C21—C20—O1—C2	170.8 (3)
C2—C1—C10—C5	−1.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1	0.93	2.32	2.961 (4)	126

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁NO
M_r	303.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.6011 (11), 20.457 (3), 7.4335 (7)
β (°)	101.303 (8)
V (Å³)	1730.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.71 × 0.55 × 0.36

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14212, 3403, 1769
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.211, 0.94
No. of reflections	3403
No. of parameters	209
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.31

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1	0.93	2.32	2.961 (4)	126

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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