organic compounds
4-[(E)-(4-Ethoxyphenyl)iminomethyl]phenol
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
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 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
|
Refinement
|
Data collection: CrysAlis PRO (Agilent, 2011); cell 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
10.1107/S1600536812034253/bt5991sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034253/bt5991Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034253/bt5991Isup3.cml
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%.
The hydroxyl hydrogen atom was found in difference Fourier maps and its coordinates were refined. All other hydrogen atoms were calculated geometrically and refined as riding on their parent atoms. The methyl H atoms were allowed to rotate freely about the adjacent C–C bond. The displacement coefficients of hydrogen atoms Uiso(H) were set to 1.5Ueq(C, O) for the methyl- and hydroxyl- groups and to to 1.2Ueq(C) for the CH– and CH2- groups.
Data collection: CrysAlis PRO (Agilent, 2011); cell
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).C15H15NO2 | F(000) = 1024 |
Mr = 241.3 | Dx = 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 |
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 | Rint = 0.028 |
Detector resolution: 10.3784 pixels mm-1 | θmax = 61.1°, θmin = 3.5° |
Rotation method data acquisition using ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −10→10 |
Tmin = 0.795, Tmax = 1 | l = −28→27 |
22644 measured reflections |
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 | Δρmax = 0.11 e Å−3 |
166 parameters | Δρmin = −0.11 e Å−3 |
0 restraints |
C15H15NO2 | V = 2571.00 (9) Å3 |
Mr = 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 |
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) |
Tmin = 0.795, Tmax = 1 | Rint = 0.028 |
22644 measured reflections | θmax = 61.1° |
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 | Δρmax = 0.11 e Å−3 |
1978 reflections | Δρmin = −0.11 e Å−3 |
166 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.795, 1 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 22644, 1978, 1780 |
Rint | 0.028 |
θmax (°) | 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 |
Δρmax, Δρmin (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).
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.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.