3-[(2,4-Dichloro­phen­yl)imino­meth­yl]-2-hydr­oxy-5-methyl­benzaldehyde

Kılıç, I.; Işık, Ş.; Ağar, E.; Erşahin, F.

doi:10.1107/S1600536809018303

organic compounds

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Volume 65| Part 6| June 2009| Page o1347

doi:10.1107/S1600536809018303

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3-[(2,4-Dichlorophenyl)iminomethyl]-2-hydroxy-5-methylbenzaldehyde

Işın Kılıç,^a ^* Şamil Işık,^a Erbil Ağar ^b and Ferda Erşahin ^b

^aDepartment of Physics, Faculty of Arts and Science, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Science, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: ikilic@omu.edu.tr

(Received 14 May 2009; accepted 14 May 2009; online 20 May 2009)

The title compound, C₁₅H₁₁Cl₂NO₂, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state, being stabilized by a strong intramolecular O—H⋯N hydrogen bond. The molecule is almost planar (r.m.s. deviation for all non-H atoms = 0.049 Å), displaying a dihedral angle of 3.1 (3)° between the planes of the two aromatic rings.

Related literature

For Schiff bases as substrates in the preparation of number of biologically active compounds, see: Siddiqui et al. (2006 ). For photochromism and thermochromism in these compounds, see: Hadjoudis et al. (1987 ); Xu et al. (1994 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Gül et al. (2007 ) Koşar et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₁Cl₂NO₂
M_r = 308.15
Monoclinic, P 2₁ /c
a = 19.424 (2) Å
b = 4.6113 (3) Å
c = 15.4245 (14) Å
β = 103.946 (8)°
V = 1340.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 296 K
0.80 × 0.31 × 0.02 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED; Stoe & Cie, 2002 ) T_min = 0.817, T_max = 0.982
5912 measured reflections
2613 independent reflections
1228 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.138
S = 0.91
2613 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.577 (4)	147

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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018303/bt2960sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018303/bt2960Isup2.hkl

checkCIF report

Comment top

In this paper, a new Schiff base, (I), C₁₅H₁₁Cl₂O₂N is prepared and its crystal structure is reported.

Schiff bases are synthesized from an aromatic amine and a carbonyl compound by a nucleophilic addition reaction. They are used as substrates in the preparation of number of biologically active compounds (Siddiqui et al., 2006). Photochromism and thermochromism are also characteristics of these materials and arise via H-atom transfer from the hydroxy O atom to the N atom (Hadjoudis et al., 1987; Xu et al., 1994). These are two types of intra molecular hydrogen bonds in Schiff bases, in keto-amine (N—H···O) and phenol-imine (N···H—O) tautomeric forms. Our X-ray investigation shows that the title compound, (I), exists in the phenol-imine form.

An ORTEP view of the molecule of (I) is shown in Fig. 1. There is a strong O···N type intramolecular hydrogen bond and this intramolecular hydrogen bond (O1—H1···N1) can be described as an S(6) motif (Bernstein et al., 1995). The C1—O1 [1.354 (6) Å] and C7=N1 [1.272 (6) Å] bond lengths verify the enol-imine form of (I), and these distances are agree with the corresponding distances in (E)-2-[4-(Dimethylamino)phenyliminomethyl]-6-methylphenol [1.350 (3) and 1.280 (2) Å; Gül et al., 2007)] and in (E)-4-Methoxy-2- [(4-nitrophenyl)iminomethyl]phenol [1.351 (2) and 1.277 (2) Å; Koşar et al., 2005]. The molecule is almost planar and the dihedral angle between the rings formed by atoms C1—C6 and C8—C13 is 3.12(0.28)°.

Related literature top

For Schiff bases as substrates in the preparation of number of biologically active compounds, see: Siddiqui et al. (2006). For photochromism and thermochromism in these compounds, see: Hadjoudis et al. (1987); Xu et al. (1994). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Gül et al. (2007) Koşar et al. (2005).

For related literature, see: .

Experimental top

The compound 3-[(2,4-Dichlorophenyl)imino]methyl-2-hydroxy-5- methylbenzaldehyde was prepared by reflux a mixture of a solution containing 2-Hydroxy-5-methyl-1,3-benzenedicarboxaldehyde (0.05 g 0.3 mmol) in 20 ml e thanol and a solution containing 2,4-Dichloroaniline(0.049 g 0.3 mmol) in 20 ml e thanol. The reaction mixture was stirred for 1 hunder reflux. The crystals of 3-[(2,4-Dichlorophenyl)imino]methyl-2-hydroxy-5- methylbenzaldehyde suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield % 79; m.p.483–485 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Dashed lines indicate intramolecular hydrogen bond.
	Fig. 2. The crystal packing of compound (I). Dashed lines indicate intramolecular hydrogen bond.
	Fig. 3. Synthetic scheme for C₁₅H₁₁Cl₂O₂N.

3-[(2,4-Dichlorophenyl)iminomethyl]-2-hydroxy-5-methylbenzaldehyde top

Crystal data top

C₁₅H₁₁Cl₂NO₂	F(000) = 632
M_r = 308.15	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6202 reflections
a = 19.424 (2) Å	θ = 1.9–29.5°
b = 4.6113 (3) Å	µ = 0.48 mm⁻¹
c = 15.4245 (14) Å	T = 296 K
β = 103.946 (8)°	Plate, red
V = 1340.9 (2) Å³	0.80 × 0.31 × 0.02 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	2613 independent reflections
Radiation source: fine-focus sealed tube	1228 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.099
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.2°
rotation method scans	h = −23→22
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −5→5
T_min = 0.817, T_max = 0.982	l = −18→18
5912 measured 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0441P)²] where P = (F_o² + 2F_c²)/3
2613 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₁Cl₂NO₂	V = 1340.9 (2) Å³
M_r = 308.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.424 (2) Å	µ = 0.48 mm⁻¹
b = 4.6113 (3) Å	T = 296 K
c = 15.4245 (14) Å	0.80 × 0.31 × 0.02 mm
β = 103.946 (8)°

Data collection top

Stoe IPDS II diffractometer	2613 independent reflections
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	1228 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.982	R_int = 0.099
5912 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 0.91	Δρ_max = 0.28 e Å⁻³
2613 reflections	Δρ_min = −0.27 e Å⁻³
183 parameters

Special details top

Experimental. 120 frames, detector distance = 100 mm

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1925 (3)	0.2637 (10)	0.3175 (3)	0.0447 (12)
C2	0.1516 (3)	0.0564 (11)	0.2629 (3)	0.0489 (12)
C3	0.0969 (3)	−0.0806 (10)	0.2900 (3)	0.0495 (13)
H3	0.0702	−0.2192	0.2528	0.059*
C4	0.0806 (2)	−0.0190 (10)	0.3702 (3)	0.0467 (12)
C5	0.1227 (2)	0.1889 (10)	0.4239 (3)	0.0472 (12)
H5	0.1134	0.2321	0.4789	0.057*
C6	0.1770 (2)	0.3330 (9)	0.3998 (3)	0.0410 (11)
C7	0.2183 (3)	0.5467 (10)	0.4580 (3)	0.0463 (12)
H7	0.2062	0.5931	0.5110	0.056*
C8	0.3140 (2)	0.8812 (9)	0.4948 (3)	0.0435 (11)
C9	0.3702 (3)	1.0022 (10)	0.4659 (3)	0.0493 (13)
C10	0.4154 (3)	1.2028 (10)	0.5178 (3)	0.0538 (14)
H10	0.4531	1.2807	0.4980	0.065*
C11	0.4039 (3)	1.2842 (10)	0.5983 (3)	0.0496 (13)
C12	0.3487 (3)	1.1723 (10)	0.6292 (3)	0.0508 (13)
H12	0.3419	1.2297	0.6843	0.061*
C13	0.3035 (3)	0.9738 (10)	0.5774 (3)	0.0500 (13)
H13	0.2656	0.9003	0.5976	0.060*
C14	0.0213 (3)	−0.1709 (12)	0.3997 (3)	0.0618 (15)
H14A	−0.0188	−0.0434	0.3918	0.093*
H14B	0.0370	−0.2233	0.4615	0.093*
H14C	0.0079	−0.3426	0.3644	0.093*
C15	0.1671 (3)	−0.0215 (13)	0.1781 (3)	0.0676 (16)
H15	0.2055	0.0712	0.1638	0.081*
Cl1	0.38664 (8)	0.8931 (3)	0.36584 (9)	0.0671 (5)
Cl2	0.46096 (7)	1.5343 (3)	0.66358 (9)	0.0634 (5)
N1	0.2710 (2)	0.6740 (8)	0.4391 (2)	0.0464 (10)
O1	0.24635 (18)	0.3927 (7)	0.2904 (2)	0.0581 (10)
H1	0.2660	0.5101	0.3282	0.087*
O2	0.1350 (2)	−0.1956 (9)	0.1242 (2)	0.0785 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.046 (3)	0.044 (3)	0.045 (3)	0.000 (2)	0.012 (2)	0.003 (2)
C2	0.051 (3)	0.056 (3)	0.039 (2)	0.002 (3)	0.010 (2)	−0.004 (2)
C3	0.055 (3)	0.050 (3)	0.041 (3)	−0.002 (2)	0.006 (2)	−0.005 (2)
C4	0.043 (3)	0.047 (3)	0.048 (3)	0.003 (2)	0.009 (2)	0.000 (2)
C5	0.050 (3)	0.049 (3)	0.042 (2)	0.005 (2)	0.010 (2)	−0.001 (2)
C6	0.047 (3)	0.037 (3)	0.037 (2)	0.001 (2)	0.006 (2)	−0.003 (2)
C7	0.055 (3)	0.044 (3)	0.041 (2)	0.005 (3)	0.015 (2)	0.004 (2)
C8	0.045 (3)	0.037 (3)	0.046 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C9	0.057 (3)	0.041 (3)	0.046 (3)	0.005 (3)	0.004 (2)	0.000 (2)
C10	0.052 (3)	0.045 (3)	0.061 (3)	−0.005 (2)	0.008 (3)	0.000 (2)
C11	0.052 (3)	0.043 (3)	0.049 (3)	0.003 (2)	0.002 (2)	0.001 (2)
C12	0.058 (3)	0.052 (3)	0.045 (3)	0.005 (3)	0.017 (2)	−0.001 (2)
C13	0.053 (3)	0.055 (3)	0.044 (3)	−0.006 (3)	0.017 (2)	−0.003 (2)
C14	0.063 (3)	0.062 (4)	0.062 (3)	−0.003 (3)	0.018 (3)	−0.007 (3)
C15	0.063 (3)	0.089 (4)	0.054 (3)	−0.012 (3)	0.021 (3)	−0.018 (3)
Cl1	0.0730 (9)	0.0789 (10)	0.0548 (7)	−0.0040 (8)	0.0263 (7)	−0.0082 (7)
Cl2	0.0617 (8)	0.0510 (8)	0.0691 (8)	−0.0052 (7)	−0.0007 (7)	−0.0080 (7)
N1	0.053 (2)	0.046 (2)	0.039 (2)	0.003 (2)	0.0093 (19)	−0.0035 (18)
O1	0.061 (2)	0.063 (2)	0.0516 (19)	−0.0117 (18)	0.0160 (17)	−0.0102 (17)
O2	0.086 (3)	0.101 (3)	0.052 (2)	−0.028 (2)	0.023 (2)	−0.026 (2)

Geometric parameters (Å, º) top

C1—O1	1.354 (6)	C8—N1	1.416 (5)
C1—C2	1.390 (6)	C9—C10	1.390 (6)
C1—C6	1.411 (7)	C9—Cl1	1.725 (5)
C2—C3	1.384 (7)	C10—C11	1.366 (7)
C2—C15	1.457 (7)	C10—H10	0.9300
C3—C4	1.378 (7)	C11—C12	1.374 (7)
C3—H3	0.9300	C11—Cl2	1.742 (5)
C4—C5	1.395 (6)	C12—C13	1.382 (6)
C4—C14	1.510 (7)	C12—H12	0.9300
C5—C6	1.371 (6)	C13—H13	0.9300
C5—H5	0.9300	C14—H14A	0.9600
C6—C7	1.440 (6)	C14—H14B	0.9600
C7—N1	1.272 (6)	C14—H14C	0.9600
C7—H7	0.9300	C15—O2	1.215 (5)
C8—C9	1.391 (7)	C15—H15	0.9300
C8—C13	1.404 (7)	O1—H1	0.8200

O1—C1—C2	119.2 (4)	C10—C9—Cl1	118.8 (4)
O1—C1—C6	121.8 (4)	C8—C9—Cl1	119.9 (4)
C2—C1—C6	119.1 (5)	C11—C10—C9	119.2 (5)
C3—C2—C1	120.0 (4)	C11—C10—H10	120.4
C3—C2—C15	120.0 (4)	C9—C10—H10	120.4
C1—C2—C15	120.0 (5)	C10—C11—C12	121.6 (5)
C4—C3—C2	122.4 (4)	C10—C11—Cl2	119.1 (4)
C4—C3—H3	118.8	C12—C11—Cl2	119.3 (4)
C2—C3—H3	118.8	C11—C12—C13	119.3 (5)
C3—C4—C5	116.5 (5)	C11—C12—H12	120.4
C3—C4—C14	122.1 (4)	C13—C12—H12	120.4
C5—C4—C14	121.4 (5)	C12—C13—C8	120.9 (5)
C6—C5—C4	123.4 (5)	C12—C13—H13	119.5
C6—C5—H5	118.3	C8—C13—H13	119.5
C4—C5—H5	118.3	C4—C14—H14A	109.5
C5—C6—C1	118.6 (4)	C4—C14—H14B	109.5
C5—C6—C7	120.8 (4)	H14A—C14—H14B	109.5
C1—C6—C7	120.5 (5)	C4—C14—H14C	109.5
N1—C7—C6	122.1 (5)	H14A—C14—H14C	109.5
N1—C7—H7	118.9	H14B—C14—H14C	109.5
C6—C7—H7	118.9	O2—C15—C2	126.4 (5)
C9—C8—C13	117.8 (4)	O2—C15—H15	116.8
C9—C8—N1	118.0 (4)	C2—C15—H15	116.8
C13—C8—N1	124.2 (5)	C7—N1—C8	124.2 (4)
C10—C9—C8	121.2 (5)	C1—O1—H1	109.5

O1—C1—C2—C3	179.1 (4)	C13—C8—C9—C10	1.5 (7)
C6—C1—C2—C3	−0.6 (7)	N1—C8—C9—C10	−178.8 (4)
O1—C1—C2—C15	0.5 (7)	C13—C8—C9—Cl1	179.0 (3)
C6—C1—C2—C15	−179.2 (4)	N1—C8—C9—Cl1	−1.3 (6)
C1—C2—C3—C4	0.2 (7)	C8—C9—C10—C11	−0.7 (7)
C15—C2—C3—C4	178.9 (4)	Cl1—C9—C10—C11	−178.2 (4)
C2—C3—C4—C5	−0.5 (7)	C9—C10—C11—C12	0.0 (7)
C2—C3—C4—C14	−179.5 (4)	C9—C10—C11—Cl2	179.7 (3)
C3—C4—C5—C6	1.2 (7)	C10—C11—C12—C13	−0.3 (7)
C14—C4—C5—C6	−179.8 (4)	Cl2—C11—C12—C13	−180.0 (4)
C4—C5—C6—C1	−1.5 (7)	C11—C12—C13—C8	1.2 (7)
C4—C5—C6—C7	179.7 (4)	C9—C8—C13—C12	−1.8 (7)
O1—C1—C6—C5	−178.5 (4)	N1—C8—C13—C12	178.5 (4)
C2—C1—C6—C5	1.2 (6)	C3—C2—C15—O2	2.4 (9)
O1—C1—C6—C7	0.3 (7)	C1—C2—C15—O2	−179.0 (5)
C2—C1—C6—C7	180.0 (4)	C6—C7—N1—C8	−178.7 (4)
C5—C6—C7—N1	176.8 (4)	C9—C8—N1—C7	179.7 (4)
C1—C6—C7—N1	−2.0 (7)	C13—C8—N1—C7	−0.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.577 (4)	147

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁Cl₂NO₂
M_r	308.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	19.424 (2), 4.6113 (3), 15.4245 (14)
β (°)	103.946 (8)
V (Å³)	1340.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.80 × 0.31 × 0.02

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED; Stoe & Cie, 2002)
T_min, T_max	0.817, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	5912, 2613, 1228
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.138, 0.91
No. of reflections	2613
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.27

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), 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	0.82	1.851	2.577 (4)	147

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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