4-[(E)-(4-Eth­oxy­phen­yl)imino­meth­yl]phenol

Khalaji, A.D.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536812034253

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2646

doi:10.1107/S1600536812034253

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4-[(E)-(4-Ethoxyphenyl)iminomethyl]phenol

Aliakbar Dehno Khalaji,^a Karla Fejfarová ^b ^* and Michal Dušek ^b

^aDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: fejfarov@fzu.cz

(Received 31 July 2012; accepted 1 August 2012; online 4 August 2012)

In the title compound, C₁₅H₁₅NO₂, the dihedral angle between the benzene rings is 52.04 (5)° and the molecule has an E conformation about the central C=N bond. In the crystal, molecules are connected by O—H⋯N hydrogen bonds, forming zigzag chains along the b axis. The crystal packing also features weak C—H⋯O interactions.

Related literature

For Schiff base derivatives and related structures, see: Fejfarová et al. (2010 ); Özek et al. (2010 ); Akkurt et al. (2008 ); Khalaji et al. (2008 , 2009 ) For applications and properties of Schiff bases, see: Dalapati et al. (2011 ); Keypour et al. (2010 ); Khalil et al. (2009 ); Khanmohammadi et al. (2009 ); Sun et al. (2012 ); Da Silva et al. (2011 ).

Experimental

Crystal data

C₁₅H₁₅NO₂
M_r = 241.3
Orthorhombic, P b c a
a = 10.9155 (2) Å
b = 9.4056 (2) Å
c = 25.0422 (5) Å
V = 2571.00 (9) Å³
Z = 8
Cu Kα radiation
μ = 0.67 mm⁻¹
T = 120 K
0.54 × 0.20 × 0.03 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.795, T_max = 1
22644 measured reflections
1978 independent reflections
1780 reflections with I > 3σ(I)
R_int = 0.028
θ_max = 61.1°

Refinement

R[F² > 3σ(F²)] = 0.031
wR(F²) = 0.103
S = 1.71
1978 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7b⋯O2ⁱ	0.96	2.50	3.3393 (15)	147
O2—H2o⋯N1ⁱⁱ	0.894 (17)	1.825 (17)	2.7098 (12)	170.0 (14)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+1, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034253/bt5991sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034253/bt5991Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034253/bt5991Isup3.cml

checkCIF report

Comment top

Schiff base compounds exhibit a broad range of biological activities, including antifungal, and antibacterial (Da Silva et al., 2011). They are used as anion sensors (Dalapati et al., 2011; Khalil et al., 2009), non-linear optics compounds (Sun et al., 2012), and as versatile ligands in coordination chemistry (Khanmohammadi et al., 2009; Keypour et al., 2010). The present work is part of a structural study of Schiff bases (Khalaji et al., 2008, 2009; Fejfarová et al., 2010) and we report here the structure of (E)-(4-hydroxybenzylidene)-4-ethoxyaniline, (1).

The molecule of (1) (Fig. 1) has an E conformation about the central C=N bond and the C=N and C—N bond lengths of 1.2853 (45) and 1.4250 (14) Å agree well with the corresponding distances in other Schiff bases (Akkurt et al., 2008; Özek et al., 2010; Khalaji et al., 2008, 2009; Fejfarová et al., 2010). The dihedral angle between the two benzene rings is 52.04 (5)°. The ethoxy group is almost coplanar with the adjacent ring [dihedral angle 3.51 (12)°]. The molecules are connected by intermolecular O—H···N hydrogen bonds, forming zigzag chains along the b axis (Fig. 2). The crystal structure is further stabilized by intermolecular C—H···O hydrogen bonds.

Related literature top

For Schiff base derivatives and related structures, see: Fejfarová et al. (2010); Özek et al. (2010); Akkurt et al. (2008); Khalaji et al. (2008, 2009) For applications and properties of Schiff bases, see: Dalapati et al. (2011); Keypour et al. (2010); Khalil et al. (2009); Khanmohammadi et al. (2009); Sun et al. (2012); Da Silva et al. (2011).

Experimental top

To a stirring solution of the 4-hydroxybenzaldehyde (0.2 mmol, in 5 ml of methanol) was added 4-ethoxyaniline (0.2 mmol) in 10 ml of methanol and the mixture was stirred for 1 h in air at 323 K and was then left at room temperature for several days without disturbance yielding suitable crystals of 1 that subsequently were filtered off and washed with Et2O. Yield: 82%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Hydrogen-bonded chain propagating along the b axis. Hydrogen bonds are drawn as dashed lines.

4-[(E)-(4-Ethoxyphenyl)iminomethyl]phenol top

Crystal data top

C₁₅H₁₅NO₂	F(000) = 1024
M_r = 241.3	D_x = 1.246 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14821 reflections
a = 10.9155 (2) Å	θ = 3.5–61.1°
b = 9.4056 (2) Å	µ = 0.67 mm⁻¹
c = 25.0422 (5) Å	T = 120 K
V = 2571.00 (9) Å³	Plate, light yellow
Z = 8	0.54 × 0.20 × 0.03 mm

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1978 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1780 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.3784 pixels mm^-1	θ_max = 61.1°, θ_min = 3.5°
Rotation method data acquisition using ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
T_min = 0.795, T_max = 1	l = −28→27
22644 measured reflections

Refinement top

Refinement on F²	57 constraints
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0025000002I²)
S = 1.71	(Δ/σ)_max = 0.006
1978 reflections	Δρ_max = 0.11 e Å⁻³
166 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints

Crystal data top

C₁₅H₁₅NO₂	V = 2571.00 (9) Å³
M_r = 241.3	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 10.9155 (2) Å	µ = 0.67 mm⁻¹
b = 9.4056 (2) Å	T = 120 K
c = 25.0422 (5) Å	0.54 × 0.20 × 0.03 mm

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1978 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1780 reflections with I > 3σ(I)
T_min = 0.795, T_max = 1	R_int = 0.028
22644 measured reflections	θ_max = 61.1°

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.71	Δρ_max = 0.11 e Å⁻³
1978 reflections	Δρ_min = −0.11 e Å⁻³
166 parameters

Special details top

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2011). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

	x	y	z	U_iso*/U_eq
O1	−0.08099 (8)	0.58106 (10)	0.55939 (4)	0.0344 (3)
O2	0.50129 (8)	−0.13939 (9)	0.85269 (3)	0.0251 (3)
N1	0.26997 (8)	0.30259 (10)	0.68326 (4)	0.0196 (3)
C1	0.18053 (10)	0.37189 (12)	0.65100 (4)	0.0200 (3)
C2	0.06035 (11)	0.32217 (13)	0.64660 (4)	0.0234 (4)
C3	−0.02398 (11)	0.39425 (13)	0.61577 (5)	0.0260 (4)
C4	0.00974 (12)	0.51683 (14)	0.58837 (4)	0.0259 (4)
C5	0.12999 (11)	0.56466 (13)	0.59109 (5)	0.0251 (4)
C6	0.21487 (11)	0.49095 (12)	0.62174 (5)	0.0228 (4)
C7	−0.04877 (15)	0.70560 (14)	0.52934 (5)	0.0357 (4)
C8	−0.16378 (16)	0.75963 (18)	0.50327 (7)	0.0509 (5)
C9	0.23493 (11)	0.24457 (11)	0.72715 (5)	0.0208 (4)
C10	0.42099 (10)	0.09397 (12)	0.74119 (5)	0.0198 (4)
C11	0.48630 (10)	−0.00196 (12)	0.77159 (4)	0.0199 (4)
C12	0.44379 (10)	−0.04176 (12)	0.82220 (4)	0.0205 (4)
C13	0.33635 (10)	0.01912 (12)	0.84201 (5)	0.0230 (4)
C14	0.27084 (11)	0.11386 (12)	0.81106 (4)	0.0228 (4)
C15	0.31179 (10)	0.15335 (12)	0.76005 (4)	0.0202 (4)
H2	0.036296	0.23732	0.665154	0.028*
H3	−0.106486	0.35958	0.613196	0.0313*
H5	0.154298	0.648332	0.571861	0.0301*
H6	0.298437	0.52267	0.622731	0.0273*
H7a	0.009871	0.680691	0.502344	0.0429*
H7b	−0.017107	0.776855	0.553066	0.0429*
H8a	−0.144624	0.840538	0.481436	0.0764*
H8b	−0.198521	0.686045	0.48144	0.0764*
H8c	−0.221636	0.786824	0.530273	0.0764*
H9	0.152732	0.262562	0.738996	0.0249*
H10	0.450945	0.120386	0.706538	0.0237*
H11	0.561133	−0.041581	0.758022	0.0239*
H13	0.308026	−0.0049	0.877165	0.0276*
H14	0.196003	0.153391	0.82466	0.0273*
H2o	0.5725 (16)	−0.1625 (16)	0.8374 (6)	0.0377*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0303 (5)	0.0399 (6)	0.0330 (5)	0.0097 (4)	−0.0083 (4)	0.0063 (4)
O2	0.0188 (5)	0.0286 (5)	0.0279 (5)	0.0040 (3)	0.0011 (3)	0.0074 (3)
N1	0.0168 (5)	0.0182 (5)	0.0238 (5)	−0.0005 (4)	−0.0022 (4)	−0.0012 (4)
C1	0.0181 (6)	0.0208 (6)	0.0210 (6)	0.0025 (4)	0.0003 (4)	−0.0033 (5)
C2	0.0218 (6)	0.0235 (7)	0.0248 (6)	−0.0005 (5)	−0.0009 (5)	−0.0002 (5)
C3	0.0180 (6)	0.0325 (7)	0.0277 (7)	0.0002 (5)	−0.0020 (5)	−0.0016 (5)
C4	0.0263 (7)	0.0303 (7)	0.0212 (6)	0.0081 (5)	−0.0028 (5)	−0.0019 (5)
C5	0.0281 (7)	0.0243 (6)	0.0229 (6)	0.0017 (5)	0.0022 (5)	0.0005 (5)
C6	0.0204 (6)	0.0238 (6)	0.0241 (6)	−0.0003 (5)	0.0014 (5)	−0.0020 (5)
C7	0.0496 (9)	0.0313 (7)	0.0262 (7)	0.0121 (6)	−0.0067 (6)	0.0008 (5)
C8	0.0644 (11)	0.0465 (9)	0.0418 (9)	0.0231 (8)	−0.0190 (8)	−0.0003 (7)
C9	0.0166 (6)	0.0199 (6)	0.0259 (7)	−0.0002 (4)	−0.0001 (5)	−0.0030 (5)
C10	0.0176 (6)	0.0207 (6)	0.0209 (6)	−0.0030 (4)	−0.0007 (4)	−0.0011 (4)
C11	0.0154 (6)	0.0205 (6)	0.0239 (6)	−0.0006 (4)	−0.0010 (4)	−0.0023 (5)
C12	0.0169 (6)	0.0196 (6)	0.0249 (6)	−0.0035 (4)	−0.0041 (4)	−0.0005 (5)
C13	0.0190 (6)	0.0271 (7)	0.0228 (6)	−0.0026 (5)	0.0014 (5)	0.0015 (5)
C14	0.0167 (6)	0.0248 (6)	0.0267 (6)	0.0005 (5)	0.0007 (5)	−0.0014 (5)
C15	0.0171 (6)	0.0193 (6)	0.0243 (6)	−0.0030 (4)	−0.0026 (5)	−0.0025 (5)

Geometric parameters (Å, º) top

O1—C4	1.3684 (15)	C7—H7a	0.96
O1—C7	1.4360 (16)	C7—H7b	0.96
O2—C12	1.3492 (14)	C8—H8a	0.96
O2—H2o	0.894 (17)	C8—H8b	0.96
N1—C1	1.4250 (14)	C8—H8c	0.96
N1—C9	1.2853 (14)	C9—C15	1.4557 (16)
C1—C2	1.3971 (16)	C9—H9	0.96
C1—C6	1.3897 (16)	C10—C11	1.3791 (16)
C2—C3	1.3795 (17)	C10—C15	1.3985 (15)
C2—H2	0.96	C10—H10	0.96
C3—C4	1.3913 (17)	C11—C12	1.4006 (15)
C3—H3	0.96	C11—H11	0.96
C4—C5	1.3892 (17)	C12—C13	1.3961 (16)
C5—C6	1.3887 (16)	C13—C14	1.3807 (16)
C5—H5	0.96	C13—H13	0.96
C6—H6	0.96	C14—C15	1.4033 (16)
C7—C8	1.504 (2)	C14—H14	0.96

C4—O1—C7	117.43 (10)	C7—C8—H8a	109.47
C12—O2—H2o	109.1 (9)	C7—C8—H8b	109.47
C1—N1—C9	118.37 (9)	C7—C8—H8c	109.47
N1—C1—C2	122.33 (10)	H8a—C8—H8b	109.47
N1—C1—C6	118.86 (10)	H8a—C8—H8c	109.47
C2—C1—C6	118.78 (10)	H8b—C8—H8c	109.47
C1—C2—C3	120.40 (11)	N1—C9—C15	124.24 (10)
C1—C2—H2	119.8	N1—C9—H9	117.88
C3—C2—H2	119.8	C15—C9—H9	117.88
C2—C3—C4	120.45 (11)	C11—C10—C15	121.02 (10)
C2—C3—H3	119.77	C11—C10—H10	119.49
C4—C3—H3	119.77	C15—C10—H10	119.49
O1—C4—C3	115.84 (11)	C10—C11—C12	120.21 (10)
O1—C4—C5	124.54 (11)	C10—C11—H11	119.89
C3—C4—C5	119.61 (11)	C12—C11—H11	119.9
C4—C5—C6	119.73 (11)	O2—C12—C11	122.68 (10)
C4—C5—H5	120.14	O2—C12—C13	117.95 (10)
C6—C5—H5	120.14	C11—C12—C13	119.35 (10)
C1—C6—C5	120.91 (11)	C12—C13—C14	120.02 (11)
C1—C6—H6	119.54	C12—C13—H13	119.99
C5—C6—H6	119.54	C14—C13—H13	119.99
O1—C7—C8	107.38 (12)	C13—C14—C15	121.12 (10)
O1—C7—H7a	109.47	C13—C14—H14	119.44
O1—C7—H7b	109.47	C15—C14—H14	119.44
C8—C7—H7a	109.47	C9—C15—C10	122.37 (10)
C8—C7—H7b	109.47	C9—C15—C14	119.18 (10)
H7a—C7—H7b	111.48	C10—C15—C14	118.24 (10)

C4—O1—C7—C8	−177.51 (11)	N1—C9—C15—C10	−15.04 (18)
C9—N1—C1—C2	−35.10 (15)	N1—C9—C15—C14	170.16 (11)
C9—N1—C1—C6	146.67 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7b···O2ⁱ	0.96	2.50	3.3393 (15)	147
O2—H2o···N1ⁱⁱ	0.894 (17)	1.825 (17)	2.7098 (12)	170.0 (14)

Symmetry codes: (i) x−1/2, y+1, −z+3/2; (ii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₂
M_r	241.3
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	10.9155 (2), 9.4056 (2), 25.0422 (5)
V (Å³)	2571.00 (9)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.54 × 0.20 × 0.03

Data collection
Diffractometer	Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.795, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	22644, 1978, 1780
R_int	0.028
θ_max (°)	61.1
(sin θ/λ)_max (Å⁻¹)	0.568

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.103, 1.71
No. of reflections	1978
No. of parameters	166
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.11

Computer programs: CrysAlis PRO (Agilent, 2011), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7b···O2ⁱ	0.96	2.50	3.3393 (15)	146.6
O2—H2o···N1ⁱⁱ	0.894 (17)	1.825 (17)	2.7098 (12)	170.0 (14)

Symmetry codes: (i) x−1/2, y+1, −z+3/2; (ii) −x+1, y−1/2, −z+3/2.

Acknowledgements

We acknowledge Golestan University for partial support of this work, the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.

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