(E)-3-Chloro-N-[(2-eth-oxy-naphthalen-1-yl)methyl-idene]aniline.

In the title compound, C(19)H(16)ClNO, the dihedral angle between the naphthalene ring system and the chloro-benzene ring is 61.90 (10)° and the C-N-C-C torsion angle is 174.6 (2)°. The mol-ecular structure is stabilized by an intra-molecular C-H⋯N hydrogen bond. The crystal structure features π-π stacking inter-actions [centroid-centroid distances = 3.7325 (17) and 3.8150 (17) Å].

Related literature

For applications of Schiff bases in the pharmaceutical industry, medicine, industry and technology, see: Güler (1998 ▶). For their biological properties, see: Lozier et al. (1975 ▶); Calligaris et al. (1972 ▶); Williams (1972 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Zhang (2009 ▶); Pavlović et al. (2002 ▶); Özdemir et al. (2003 ▶); Inaç et al. (2012 ▶); Ağar et al. (2010 ▶).

Experimental

Crystal data

C19H16ClNO

M = 309.78

Triclinic,

a = 8.0084 (14) Å

b = 8.7315 (19) Å

c = 11.7043 (8) Å

α = 76.253 (13)°

β = 79.794 (10)°

γ = 84.337 (17)°

V = 781.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.3 × 0.25 × 0.15 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA and X-RED32; Stoe & Cie, 2001 ▶) T min = 0.793, T max = 1.000

5144 measured reflections

3057 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.180

S = 1.05

3057 reflections

227 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.32 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001 ▶); 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, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032114/bx2419sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032114/bx2419Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032114/bx2419Isup3.cml

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

C19H16ClNO	Z = 2
Mr = 309.78	F(000) = 324
Triclinic, P1	Dx = 1.317 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0084 (14) Å	Cell parameters from 1666 reflections
b = 8.7315 (19) Å	θ = 3.3–28.7°
c = 11.7043 (8) Å	µ = 0.25 mm−1
α = 76.253 (13)°	T = 296 K
β = 79.794 (10)°	Prism, yellow
γ = 84.337 (17)°	0.3 × 0.25 × 0.15 mm
V = 781.0 (2) Å3

Stoe IPDS II two-circle diffractometer	3057 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2098 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 16.0454 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (X-AREA and X-RED32; Stoe & Cie, 2001)	k = −10→6
Tmin = 0.793, Tmax = 1.000	l = −14→14
5144 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0836P)2 + 0.0386P] where P = (Fo2 + 2Fc2)/3
3057 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.1125 (3)	−0.4097 (4)	0.1075 (3)	0.0711 (9)
C2	0.1030 (4)	−0.4953 (4)	0.2214 (3)	0.0742 (9)
C3	0.1347 (4)	−0.4241 (4)	0.3093 (3)	0.0672 (8)
C4	0.1766 (3)	−0.2695 (3)	0.2822 (2)	0.0556 (6)
C5	0.1905 (3)	−0.1770 (3)	0.1640 (2)	0.0479 (6)
C6	0.1568 (3)	−0.2514 (3)	0.0751 (2)	0.0568 (7)
C7	0.1717 (3)	−0.1636 (4)	−0.0440 (2)	0.0647 (8)
C8	0.2206 (3)	−0.0141 (4)	−0.0766 (2)	0.0622 (7)
C9	0.2572 (3)	0.0618 (3)	0.01000 (19)	0.0516 (6)
C10	0.2407 (3)	−0.0173 (3)	0.12978 (18)	0.0463 (6)
C11	0.2871 (3)	0.0684 (3)	0.21183 (19)	0.0463 (5)
C12	0.3167 (3)	0.1180 (3)	0.39163 (17)	0.0443 (5)
C13	0.2129 (3)	0.1546 (3)	0.49135 (19)	0.0519 (6)
H13	0.1021	0.1226	0.5121	0.062*
C14	0.2746 (3)	0.2383 (3)	0.5593 (2)	0.0587 (7)
H14	0.2037	0.2650	0.6246	0.070*
C15	0.4401 (3)	0.2833 (3)	0.5319 (2)	0.0570 (6)
H15	0.4814	0.3395	0.5781	0.068*
C16	0.5424 (3)	0.2431 (3)	0.43502 (19)	0.0514 (6)
C17	0.4833 (3)	0.1615 (3)	0.36474 (18)	0.0478 (6)
H17	0.5549	0.1355	0.2995	0.057*
C18	0.3509 (3)	0.2904 (3)	−0.13867 (19)	0.0616 (7)
H18A	0.2530	0.3109	−0.1796	0.074*
H18B	0.4349	0.2246	−0.1785	0.074*
C19	0.4234 (4)	0.4418 (4)	−0.1407 (2)	0.0731 (8)
H19A	0.4575	0.4964	−0.2218	0.110*
H19B	0.5203	0.4202	−0.1002	0.110*
H19C	0.3391	0.5062	−0.1015	0.110*
Cl1	0.75193 (9)	0.29581 (10)	0.40024 (6)	0.0792 (3)
O1	0.3019 (2)	0.2125 (2)	−0.01705 (13)	0.0651 (5)
N1	0.2496 (3)	0.0308 (2)	0.32487 (15)	0.0513 (5)
H1	0.100 (4)	−0.449 (4)	0.045 (3)	0.100 (11)*
H2	0.076 (4)	−0.609 (5)	0.246 (3)	0.106 (11)*
H3	0.125 (5)	−0.485 (5)	0.387 (3)	0.128 (14)*
H4	0.197 (3)	−0.222 (3)	0.344 (2)	0.072 (8)*
H7	0.154 (4)	−0.209 (4)	−0.107 (2)	0.085 (9)*
H8	0.232 (3)	0.048 (3)	−0.159 (2)	0.054 (6)*
H11	0.352 (3)	0.164 (3)	0.1718 (19)	0.048 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0488 (15)	0.087 (2)	0.092 (2)	−0.0112 (14)	−0.0097 (14)	−0.048 (2)
C2	0.0591 (17)	0.066 (2)	0.101 (3)	−0.0156 (14)	0.0025 (15)	−0.0316 (19)
C3	0.0612 (17)	0.0616 (19)	0.0737 (19)	−0.0087 (13)	0.0030 (13)	−0.0132 (16)
C4	0.0558 (15)	0.0559 (17)	0.0557 (15)	−0.0067 (11)	−0.0038 (11)	−0.0158 (13)
C5	0.0385 (12)	0.0591 (16)	0.0510 (13)	0.0016 (10)	−0.0099 (9)	−0.0217 (12)
C6	0.0416 (13)	0.0746 (19)	0.0641 (16)	0.0000 (11)	−0.0107 (10)	−0.0346 (14)
C7	0.0607 (16)	0.088 (2)	0.0599 (16)	0.0032 (14)	−0.0191 (12)	−0.0404 (16)
C8	0.0665 (16)	0.086 (2)	0.0394 (14)	0.0064 (14)	−0.0172 (11)	−0.0224 (14)
C9	0.0552 (14)	0.0638 (17)	0.0378 (12)	0.0032 (11)	−0.0113 (9)	−0.0151 (11)
C10	0.0454 (12)	0.0582 (15)	0.0385 (12)	0.0012 (10)	−0.0105 (9)	−0.0164 (10)
C11	0.0505 (13)	0.0500 (14)	0.0408 (12)	−0.0008 (10)	−0.0113 (9)	−0.0126 (11)
C12	0.0597 (14)	0.0403 (13)	0.0329 (11)	−0.0023 (10)	−0.0128 (9)	−0.0046 (9)
C13	0.0580 (15)	0.0598 (16)	0.0400 (12)	−0.0040 (11)	−0.0113 (10)	−0.0123 (11)
C14	0.0674 (17)	0.0709 (18)	0.0413 (13)	0.0027 (13)	−0.0109 (11)	−0.0205 (12)
C15	0.0750 (17)	0.0586 (16)	0.0436 (13)	−0.0063 (12)	−0.0201 (11)	−0.0151 (12)
C16	0.0622 (15)	0.0508 (15)	0.0407 (12)	−0.0116 (11)	−0.0159 (10)	−0.0005 (11)
C17	0.0593 (14)	0.0496 (14)	0.0325 (11)	−0.0040 (10)	−0.0071 (9)	−0.0050 (10)
C18	0.0633 (16)	0.080 (2)	0.0346 (12)	0.0044 (13)	−0.0065 (10)	−0.0043 (12)
C19	0.0744 (19)	0.077 (2)	0.0536 (16)	0.0060 (15)	−0.0002 (13)	0.0011 (14)
Cl1	0.0712 (5)	0.1066 (7)	0.0619 (5)	−0.0328 (4)	−0.0157 (3)	−0.0082 (4)
O1	0.0954 (14)	0.0659 (13)	0.0335 (9)	−0.0121 (10)	−0.0121 (8)	−0.0060 (8)
N1	0.0615 (12)	0.0582 (13)	0.0373 (10)	−0.0089 (9)	−0.0095 (8)	−0.0136 (9)

C1—C2	1.358 (5)	C11—H11	1.00 (2)
C1—C6	1.407 (4)	C12—C17	1.385 (3)
C1—H1	0.90 (3)	C12—C13	1.391 (3)
C2—C3	1.392 (4)	C12—N1	1.411 (3)
C2—H2	1.00 (4)	C13—C14	1.377 (3)
C3—C4	1.372 (4)	C13—H13	0.9300
C3—H3	0.93 (4)	C14—C15	1.381 (4)
C4—C5	1.418 (3)	C14—H14	0.9300
C4—H4	0.96 (3)	C15—C16	1.372 (3)
C5—C6	1.425 (3)	C15—H15	0.9300
C5—C10	1.434 (3)	C16—C17	1.375 (3)
C6—C7	1.413 (4)	C16—Cl1	1.737 (2)
C7—C8	1.347 (4)	C17—H17	0.9300
C7—H7	0.95 (3)	C18—O1	1.427 (3)
C8—C9	1.420 (3)	C18—C19	1.488 (4)
C8—H8	0.98 (2)	C18—H18A	0.9700
C9—O1	1.347 (3)	C18—H18B	0.9700
C9—C10	1.397 (3)	C19—H19A	0.9600
C10—C11	1.464 (3)	C19—H19B	0.9600
C11—N1	1.273 (3)	C19—H19C	0.9600
C2—C1—C6	121.8 (3)	C17—C12—C13	119.2 (2)
C2—C1—H1	124 (2)	C17—C12—N1	122.46 (19)
C6—C1—H1	114 (2)	C13—C12—N1	118.3 (2)
C1—C2—C3	119.3 (3)	C14—C13—C12	119.9 (2)
C1—C2—H2	123.2 (19)	C14—C13—H13	120.0
C3—C2—H2	117.6 (19)	C12—C13—H13	120.0
C4—C3—C2	121.0 (3)	C13—C14—C15	120.9 (2)
C4—C3—H3	122 (2)	C13—C14—H14	119.5
C2—C3—H3	118 (2)	C15—C14—H14	119.5
C3—C4—C5	121.4 (3)	C16—C15—C14	118.6 (2)
C3—C4—H4	120.0 (16)	C16—C15—H15	120.7
C5—C4—H4	118.6 (16)	C14—C15—H15	120.7
C4—C5—C6	116.9 (2)	C15—C16—C17	121.7 (2)
C4—C5—C10	123.8 (2)	C15—C16—Cl1	119.33 (18)
C6—C5—C10	119.2 (2)	C17—C16—Cl1	119.01 (18)
C1—C6—C7	121.9 (2)	C16—C17—C12	119.7 (2)
C1—C6—C5	119.5 (3)	C16—C17—H17	120.2
C7—C6—C5	118.5 (3)	C12—C17—H17	120.2
C8—C7—C6	122.3 (2)	O1—C18—C19	107.9 (2)
C8—C7—H7	116.0 (18)	O1—C18—H18A	110.1
C6—C7—H7	121.6 (18)	C19—C18—H18A	110.1
C7—C8—C9	120.2 (3)	O1—C18—H18B	110.1
C7—C8—H8	123.2 (14)	C19—C18—H18B	110.1
C9—C8—H8	116.6 (14)	H18A—C18—H18B	108.4
O1—C9—C10	117.03 (19)	C18—C19—H19A	109.5
O1—C9—C8	122.7 (2)	C18—C19—H19B	109.5
C10—C9—C8	120.2 (3)	H19A—C19—H19B	109.5
C9—C10—C5	119.4 (2)	C18—C19—H19C	109.5
C9—C10—C11	116.3 (2)	H19A—C19—H19C	109.5
C5—C10—C11	124.1 (2)	H19B—C19—H19C	109.5
N1—C11—C10	125.3 (2)	C9—O1—C18	119.71 (19)
N1—C11—H11	120.4 (12)	C11—N1—C12	118.1 (2)
C10—C11—H11	114.3 (12)
C6—C1—C2—C3	1.2 (4)	C6—C5—C10—C9	−0.6 (3)
C1—C2—C3—C4	−0.5 (4)	C4—C5—C10—C11	1.4 (3)
C2—C3—C4—C5	−0.6 (4)	C6—C5—C10—C11	−176.68 (19)
C3—C4—C5—C6	0.8 (3)	C9—C10—C11—N1	165.2 (2)
C3—C4—C5—C10	−177.3 (2)	C5—C10—C11—N1	−18.7 (4)
C2—C1—C6—C7	178.1 (2)	C17—C12—C13—C14	2.4 (3)
C2—C1—C6—C5	−0.9 (4)	N1—C12—C13—C14	179.4 (2)
C4—C5—C6—C1	−0.1 (3)	C12—C13—C14—C15	−1.8 (4)
C10—C5—C6—C1	178.1 (2)	C13—C14—C15—C16	0.2 (4)
C4—C5—C6—C7	−179.1 (2)	C14—C15—C16—C17	0.7 (4)
C10—C5—C6—C7	−0.9 (3)	C14—C15—C16—Cl1	−179.04 (19)
C1—C6—C7—C8	−177.3 (2)	C15—C16—C17—C12	0.0 (4)
C5—C6—C7—C8	1.7 (4)	Cl1—C16—C17—C12	179.73 (17)
C6—C7—C8—C9	−0.9 (4)	C13—C12—C17—C16	−1.5 (3)
C7—C8—C9—O1	−178.1 (2)	N1—C12—C17—C16	−178.4 (2)
C7—C8—C9—C10	−0.8 (4)	C10—C9—O1—C18	168.6 (2)
O1—C9—C10—C5	178.94 (19)	C8—C9—O1—C18	−14.0 (3)
C8—C9—C10—C5	1.5 (3)	C19—C18—O1—C9	−169.7 (2)
O1—C9—C10—C11	−4.7 (3)	C10—C11—N1—C12	174.6 (2)
C8—C9—C10—C11	177.9 (2)	C17—C12—N1—C11	−42.5 (3)
C4—C5—C10—C9	177.4 (2)	C13—C12—N1—C11	140.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1	0.96 (3)	2.24 (3)	2.915 (3)	127 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1	0.96 (3)	2.24 (3)	2.915 (3)	127 (2)