2-[(E)-4-Quinolylmethyl­ideneamino]­phenol

Yıldırım, S.Ö.; Akkurt, M.; Gümüş, M.K.; Canlıca, M.; Kaban, Ş.; McKee, V.

doi:10.1107/S1600536808033928

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2168

doi:10.1107/S1600536808033928

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2-[(E)-4-Quinolylmethylideneamino]phenol

Sema Öztürk Yıldırım,^a Mehmet Akkurt,^a ^* Mustafa Kemal Gümüş,^b Mevlüde Canlıca,^b Şeniz Kaban ^b and Vickie McKee ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bChemistry Department, Yıldız Technical University, Davutpasa Campus, Esenler 34220, Istanbul, Turkey, and ^cChemistry Department, Loughborough University, Loughborough, Leicestershire LE11 3TU, England
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 25 September 2008; accepted 17 October 2008; online 22 October 2008)

In the title compound, C₁₆H₁₂N₂O, the dihedral angle between the two aromatic ring systems is 68.54 (5)°. The molecular packing is stabilized by intra- and intermolecular O—H⋯N and intramolecular C—H⋯N hydrogen-bond interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For general background, see: Gao et al. (2005 ); Hagen et al. (1983 ); Lozytska et al. (2004 ); Sessler et al. (2004 ); Kuz'min et al. (2000 ). For related structures, see: Räisänen, Elo et al. (2007 ); Räisänen Leskelä & Repo (2007 ). For experimental procedures, see: Gümüş (2002 ).

Experimental

Crystal data

C₁₆H₁₂N₂O
M_r = 248.28
Monoclinic, P 2₁ /n
a = 6.7174 (6) Å
b = 23.931 (2) Å
c = 7.7495 (6) Å
β = 105.521 (1)°
V = 1200.33 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 (2) K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.978, T_max = 0.991
12294 measured reflections
2991 independent reflections
2338 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.105
S = 1.05
2991 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.95 (2)	2.34 (2)	2.7766 (16)	107.5 (15)
O1—H1⋯N2ⁱ	0.95 (2)	1.91 (2)	2.8085 (16)	156.4 (19)
C13—H13⋯N1	0.975 (15)	2.356 (14)	2.9776 (17)	121.0 (11)
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033928/hb2807sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033928/hb2807Isup2.hkl

checkCIF report

Comment top

2- and 4-(N-arylimino)quinolines have been investigated to their clinical efficacy for use as an analgetic drug (Hagen et al., 1983). A number of azomethines and their complexes possess high biological activity, including antineoplastic (Kuz'min et al., 2000; Gao et al., 2005) and antiviral (Lozytska et al., 2004). It has been recently shown that the macrocyclic Schiff bases can selectively bind different anions acting as artificial anionic receptors (Sessler et al., 2004).

In the title compound, (I), (Fig. 1), all bond lengths and angles are within normal ranges (Räisänen, Elo et al., 2007; Räisänen Leskelä, & Repo 2007; Allen et al., 1987). The molecule has a non-planar conformation. The dihedral angle between its two aromatic ring systems (C1–C6) and (N2/C8—C16) is 68.54 (5)°. The C6—N1—C7—C8 torsion angle is -179.98 (13)° and the N1—C6—C1—O1 angle deviates from zero only by -7.27 (18)°.

The molecular packing of the compound is stabilized by O—H···N and C—H···N hydrogen bonds (Table 1, Fig. 2).

Related literature top

For bond-length data, see: Allen et al. (1987). For general background, see: Gao et al. (2005); Hagen et al. (1983); Lozytska et al. (2004); Sessler et al. (2004); Kuz'min et al. (2000). For related structures, see: Räisänen, Elo et al. (2007); Räisänen Leskelä & Repo (2007). For experimental procedures, see: Gümüş (2002).

Experimental top

Quinoline-4-carboxaldehyde (1.0 mmol) was dissolved in hot absolute ethanol (5 ml) and an equimolar amount of 2-aminophenol dissolved in hot absolute ethanol (10 ml) was added. The mixture was refluxed at reaction temperature for 2 h. The progress of the reaction was monitored by TLC using n-hexane/ethylacetate (1:1 v/v) as eluent. Upon completion of the reaction, the crude product which precipitated on cooling was collected by filtration. Further purification was accomplished by recrystallization from ethanol to yield yellow blocks of (I). [yield 80%, m.p. 475–476 K]. UV (CHCl₃): λ_max248, 343, 377 nm. IR (KBr): 3029, 2851, 1625, 1574 and1472, 1293–1165, 830 and 757 cm^{-1. 1}H NMR (CDCl₃, 200 MHz): δ(p.p.m.) 6.95–9.08 (m, ArH and CH, 11H), 9.41(s, OH, 1H). MS: m/z 249 (M+1), 248 (M+), 247 (M-1), 128 (M-120), 120 (M-128). Analysis calculated for C₁₆H₁₂N₂O: C 77.40, H 4.87, N 11.28%; found: C 77.62, H 4.96, N 11.12% (Gümüş, 2002).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I): displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. The hydrogen bonding interactions of (I) viewed down the a axis. For clarity, H atoms not involved in hydrogen bonding have been omitted.

2-[(E)-4-Quinolylmethylideneamino]phenol top

Crystal data top

C₁₆H₁₂N₂O	F(000) = 520
M_r = 248.28	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2762 reflections
a = 6.7174 (6) Å	θ = 2.9–26.4°
b = 23.931 (2) Å	µ = 0.09 mm⁻¹
c = 7.7495 (6) Å	T = 150 K
β = 105.521 (1)°	Block, yellow
V = 1200.33 (17) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2991 independent reflections
Radiation source: sealed tube	2338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
T_min = 0.978, T_max = 0.991	k = −31→31
12294 measured reflections	l = −10→10

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)] = 0.042	Hydrogen site location: difmap and geom
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0424P)² + 0.3303P] where P = (F_o² + 2F_c²)/3
2991 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₂N₂O	V = 1200.33 (17) Å³
M_r = 248.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.7174 (6) Å	µ = 0.09 mm⁻¹
b = 23.931 (2) Å	T = 150 K
c = 7.7495 (6) Å	0.25 × 0.20 × 0.10 mm
β = 105.521 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2991 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2338 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.991	R_int = 0.037
12294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.25 e Å⁻³
2991 reflections	Δρ_min = −0.24 e Å⁻³
220 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	1.06305 (16)	0.13183 (4)	0.54890 (14)	0.0340 (3)
N1	0.76446 (16)	0.10349 (4)	0.72156 (14)	0.0243 (3)
N2	0.80975 (16)	−0.03956 (5)	1.22446 (15)	0.0258 (3)
C1	0.8930 (2)	0.16414 (5)	0.52971 (17)	0.0264 (4)
C2	0.8697 (3)	0.20982 (6)	0.41486 (19)	0.0340 (4)
C3	0.6997 (3)	0.24448 (6)	0.3910 (2)	0.0372 (5)
C4	0.5529 (3)	0.23493 (6)	0.4839 (2)	0.0370 (5)
C5	0.5745 (2)	0.18955 (6)	0.59862 (19)	0.0313 (4)
C6	0.7433 (2)	0.15362 (5)	0.62205 (17)	0.0242 (4)
C7	0.72483 (19)	0.10243 (5)	0.87303 (17)	0.0235 (3)
C8	0.74355 (18)	0.05168 (5)	0.98390 (16)	0.0215 (3)
C9	0.78135 (19)	0.05904 (6)	1.16557 (17)	0.0236 (3)
C10	0.81518 (19)	0.01260 (6)	1.28017 (17)	0.0260 (4)
C11	0.76319 (18)	−0.04841 (5)	1.04285 (17)	0.0233 (3)
C12	0.72937 (18)	−0.00427 (5)	0.91566 (16)	0.0212 (3)
C13	0.67854 (19)	−0.01837 (6)	0.73121 (17)	0.0240 (4)
C14	0.6654 (2)	−0.07303 (6)	0.67751 (18)	0.0278 (4)
C15	0.7014 (2)	−0.11657 (6)	0.8042 (2)	0.0308 (4)
C16	0.7487 (2)	−0.10454 (5)	0.98290 (19)	0.0282 (4)
H1	1.068 (3)	0.1013 (9)	0.628 (3)	0.072 (6)*
H2	0.976 (3)	0.2161 (7)	0.350 (2)	0.044 (5)*
H3	0.686 (3)	0.2753 (7)	0.307 (2)	0.046 (5)*
H4	0.433 (3)	0.2587 (7)	0.469 (2)	0.042 (5)*
H5	0.468 (2)	0.1808 (6)	0.657 (2)	0.033 (4)*
H7	0.689 (2)	0.1376 (6)	0.929 (2)	0.031 (4)*
H9	0.788 (2)	0.0966 (6)	1.214 (2)	0.031 (4)*
H10	0.844 (2)	0.0186 (6)	1.409 (2)	0.024 (4)*
H13	0.653 (2)	0.0114 (6)	0.642 (2)	0.025 (4)*
H14	0.632 (2)	−0.0822 (6)	0.550 (2)	0.032 (4)*
H15	0.693 (2)	−0.1566 (7)	0.765 (2)	0.035 (4)*
H16	0.772 (2)	−0.1340 (7)	1.074 (2)	0.033 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0385 (6)	0.0322 (5)	0.0359 (6)	0.0058 (4)	0.0181 (4)	0.0097 (4)
N1	0.0246 (5)	0.0223 (5)	0.0254 (6)	0.0006 (4)	0.0055 (4)	0.0023 (4)
N2	0.0220 (5)	0.0295 (6)	0.0259 (6)	0.0025 (4)	0.0062 (4)	0.0040 (5)
C1	0.0343 (7)	0.0221 (6)	0.0214 (6)	−0.0012 (5)	0.0049 (5)	−0.0020 (5)
C2	0.0475 (9)	0.0274 (7)	0.0272 (7)	−0.0040 (6)	0.0100 (6)	0.0022 (6)
C3	0.0549 (10)	0.0214 (7)	0.0308 (8)	−0.0020 (6)	0.0037 (7)	0.0037 (6)
C4	0.0436 (9)	0.0238 (7)	0.0383 (8)	0.0074 (6)	0.0018 (7)	0.0010 (6)
C5	0.0335 (7)	0.0257 (7)	0.0328 (7)	0.0021 (6)	0.0057 (6)	0.0002 (6)
C6	0.0303 (7)	0.0185 (6)	0.0217 (6)	−0.0016 (5)	0.0036 (5)	−0.0009 (5)
C7	0.0226 (6)	0.0221 (6)	0.0249 (6)	0.0003 (5)	0.0050 (5)	−0.0017 (5)
C8	0.0168 (6)	0.0238 (6)	0.0238 (6)	−0.0003 (5)	0.0052 (4)	0.0004 (5)
C9	0.0211 (6)	0.0251 (6)	0.0248 (6)	−0.0007 (5)	0.0064 (5)	−0.0023 (5)
C10	0.0227 (6)	0.0345 (7)	0.0210 (6)	0.0009 (5)	0.0060 (5)	0.0005 (5)
C11	0.0173 (6)	0.0259 (6)	0.0269 (6)	0.0004 (5)	0.0062 (5)	0.0017 (5)
C12	0.0166 (6)	0.0234 (6)	0.0241 (6)	0.0000 (4)	0.0064 (4)	−0.0004 (5)
C13	0.0212 (6)	0.0266 (7)	0.0247 (6)	0.0006 (5)	0.0070 (5)	0.0001 (5)
C14	0.0249 (6)	0.0297 (7)	0.0285 (7)	−0.0002 (5)	0.0068 (5)	−0.0056 (5)
C15	0.0282 (7)	0.0240 (7)	0.0388 (8)	0.0006 (5)	0.0064 (6)	−0.0036 (6)
C16	0.0257 (7)	0.0224 (6)	0.0358 (7)	0.0012 (5)	0.0071 (5)	0.0036 (6)

Geometric parameters (Å, º) top

O1—C1	1.3542 (17)	C11—C12	1.4210 (17)
O1—H1	0.95 (2)	C12—C13	1.4186 (18)
N1—C6	1.4126 (16)	C13—C14	1.368 (2)
N1—C7	1.2715 (17)	C14—C15	1.408 (2)
N2—C11	1.3740 (17)	C15—C16	1.366 (2)
N2—C10	1.3181 (19)	C2—H2	0.989 (19)
C1—C2	1.3918 (19)	C3—H3	0.972 (16)
C1—C6	1.4042 (19)	C4—H4	0.967 (19)
C2—C3	1.383 (3)	C5—H5	0.966 (14)
C3—C4	1.387 (3)	C7—H7	1.005 (15)
C4—C5	1.386 (2)	C9—H9	0.971 (15)
C5—C6	1.3957 (19)	C10—H10	0.975 (15)
C7—C8	1.4735 (17)	C13—H13	0.975 (15)
C8—C9	1.3734 (18)	C14—H14	0.978 (15)
C8—C12	1.4334 (17)	C15—H15	1.002 (17)
C9—C10	1.403 (2)	C16—H16	0.980 (16)
C11—C16	1.4161 (17)

C1—O1—H1	113.2 (13)	C13—C14—C15	120.70 (13)
C6—N1—C7	120.37 (11)	C14—C15—C16	120.07 (13)
C10—N2—C11	117.40 (11)	C11—C16—C15	120.62 (12)
O1—C1—C2	117.77 (13)	C1—C2—H2	118.1 (10)
C2—C1—C6	119.56 (13)	C3—C2—H2	121.6 (10)
O1—C1—C6	122.67 (11)	C2—C3—H3	118.1 (12)
C1—C2—C3	120.27 (16)	C4—C3—H3	121.3 (12)
C2—C3—C4	120.54 (14)	C3—C4—H4	121.7 (10)
C3—C4—C5	119.68 (16)	C5—C4—H4	118.6 (10)
C4—C5—C6	120.53 (14)	C4—C5—H5	120.4 (9)
N1—C6—C1	116.70 (11)	C6—C5—H5	118.9 (9)
C1—C6—C5	119.40 (12)	N1—C7—H7	121.0 (8)
N1—C6—C5	123.63 (12)	C8—C7—H7	115.6 (8)
N1—C7—C8	123.26 (11)	C8—C9—H9	119.5 (9)
C7—C8—C12	124.61 (11)	C10—C9—H9	120.4 (9)
C9—C8—C12	118.28 (11)	N2—C10—H10	117.1 (9)
C7—C8—C9	117.10 (11)	C9—C10—H10	119.1 (9)
C8—C9—C10	120.11 (13)	C12—C13—H13	119.3 (9)
N2—C10—C9	123.87 (12)	C14—C13—H13	119.9 (9)
N2—C11—C16	117.33 (11)	C13—C14—H14	120.0 (9)
C12—C11—C16	119.56 (12)	C15—C14—H14	119.3 (9)
N2—C11—C12	123.11 (11)	C14—C15—H15	120.7 (9)
C8—C12—C13	124.63 (11)	C16—C15—H15	119.2 (9)
C11—C12—C13	118.22 (11)	C11—C16—H16	117.5 (9)
C8—C12—C11	117.13 (11)	C15—C16—H16	121.8 (9)
C12—C13—C14	120.82 (12)

C7—N1—C6—C1	141.39 (13)	C7—C8—C9—C10	−175.57 (12)
C7—N1—C6—C5	−44.64 (19)	C12—C8—C9—C10	3.15 (19)
C6—N1—C7—C8	−179.98 (13)	C7—C8—C12—C11	176.39 (12)
C11—N2—C10—C9	−1.61 (19)	C7—C8—C12—C13	−5.5 (2)
C10—N2—C11—C12	2.52 (19)	C9—C8—C12—C11	−2.23 (18)
C10—N2—C11—C16	−177.36 (12)	C9—C8—C12—C13	175.91 (13)
O1—C1—C2—C3	−179.58 (13)	C8—C9—C10—N2	−1.3 (2)
C6—C1—C2—C3	−0.4 (2)	N2—C11—C12—C8	−0.62 (19)
O1—C1—C6—N1	−7.27 (18)	N2—C11—C12—C13	−178.87 (12)
O1—C1—C6—C5	178.49 (12)	C16—C11—C12—C8	179.26 (12)
C2—C1—C6—N1	173.54 (12)	C16—C11—C12—C13	1.00 (18)
C2—C1—C6—C5	−0.70 (19)	N2—C11—C16—C15	179.50 (13)
C1—C2—C3—C4	1.4 (2)	C12—C11—C16—C15	−0.4 (2)
C2—C3—C4—C5	−1.4 (2)	C8—C12—C13—C14	−179.03 (13)
C3—C4—C5—C6	0.4 (2)	C11—C12—C13—C14	−0.92 (19)
C4—C5—C6—N1	−173.12 (13)	C12—C13—C14—C15	0.2 (2)
C4—C5—C6—C1	0.7 (2)	C13—C14—C15—C16	0.4 (2)
N1—C7—C8—C9	153.65 (13)	C14—C15—C16—C11	−0.3 (2)
N1—C7—C8—C12	−25.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95 (2)	2.34 (2)	2.7766 (16)	107.5 (15)
O1—H1···N2ⁱ	0.95 (2)	1.91 (2)	2.8085 (16)	156.4 (19)
C13—H13···N1	0.975 (15)	2.356 (14)	2.9776 (17)	121.0 (11)

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O
M_r	248.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	6.7174 (6), 23.931 (2), 7.7495 (6)
β (°)	105.521 (1)
V (Å³)	1200.33 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.978, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	12294, 2991, 2338
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.105, 1.05
No. of reflections	2991
No. of parameters	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95 (2)	2.34 (2)	2.7766 (16)	107.5 (15)
O1—H1···N2ⁱ	0.95 (2)	1.91 (2)	2.8085 (16)	156.4 (19)
C13—H13···N1	0.975 (15)	2.356 (14)	2.9776 (17)	121.0 (11)

Symmetry code: (i) −x+2, −y, −z+2.

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Volume 64| Part 11| November 2008| Page o2168

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