Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032266/bh2113sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032266/bh2113Isup2.hkl |
CCDC reference: 659093
The title compound was prepared by refluxing a mixture of a solution containing 3-methylsalicylaldehyde (0.1 ml, 0.82 mmol) in 20 ml e thanol and a solution containing 2-aminobenzylalcohol (0.1 g, 0.82 mmol) in 20 ml e thanol. The reaction mixture was refluxed for 1 h. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethylalcohol solution (yield 15%; m.p. 377–379 K).
H atoms of the hydroxyl groups were refined with O—H constrained to 0.82 Å and Uiso(H) = 1.5Ueq(O). All other H atoms were placed in calculated positions and constrained to ride on their parents atoms, with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C). 986 measured Friedel pairs were merged before the final refinement cycles.
In this paper we present the crystal and molecular structures of a Schiff base, C15H15NO2. Recently, Schiff bases have been widely investigated for their properties and applications in different fields, such as catalysis and materials chemistry (Sabater et al., 2001; Di Bella, 2001). Schiff bases derived from 2-hydroxy-1-naphthaldehyde with various alkyl or aryl N-substituents, apart from excellent donor abilities, exhibit interesting photo- and thermo-chromic features. There are two types of intramolecular hydrogen bonds in Schiff bases, which may be stabilized in keto–amine (N—H···O hydrogen bond) or phenol–imine (N···H—O hydrogen bond) tautomeric forms. The present X-ray investigation shows that the title compound exists in the phenol–imine form (Fig. 1).
The C1—N1 and C7—C8 bond lengths are 1.408 (4) and 1.442 (4) Å, respectively, and agree with the corresponding distances in (E)-2-[4-(dimethylamino)phenyliminomethyl]-6-methylphenol [1.412 (2) and 1.441 (3) Å; Gül et al., 2007]. The C7═N1 and O1—C13 bond lengths are 1.279 (4) and 1.357 (4) Å, respectively, and agree with the corresponding distances in 2-[2-(hydroxymethyl)phenyliminomethyl]phenol [1.275 (2) and 1.354 (2) Å; Ersanlı et al., 2004]. Fig.1 also shows a strong intramolecular hydrogen bond, O1—H1···N1, describing a S(6) motif. Atom O2 in the asymmetric unit acts as hydrogen–bond donor, via H2A, connecting this molecule to O2 in a symmetry related molecule at (x + 1/2, -y + 5/2, -z), forming a C(2) chain running parallel to the [100] direction (Fig. 2).
Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Cohen et al., 1964; Hadjoudis et al., 1987). Structures related to the title compound may be found in: Ersanlı et al. (2004); Gül et al. (2007). For applications of related Schiff bases, see: Sabater et al. (2001); Di Bella (2001).
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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H15NO2 | Dx = 1.281 Mg m−3 |
Mr = 241.28 | Melting point = 377–379 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 8449 reflections |
a = 4.7829 (4) Å | θ = 1.9–29.1° |
b = 12.7379 (13) Å | µ = 0.09 mm−1 |
c = 20.532 (2) Å | T = 296 K |
V = 1250.9 (2) Å3 | Prism, yellow |
Z = 4 | 0.80 × 0.70 × 0.46 mm |
F(000) = 512 |
Stoe IPDSII diffractometer | 1460 independent reflections |
Radiation source: fine-focus sealed tube | 787 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.129 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.9° |
ω scans | h = −5→5 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −15→15 |
Tmin = 0.958, Tmax = 0.994 | l = −25→25 |
11194 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 0.79 | w = 1/[σ2(Fo2) + (0.0356P)2] where P = (Fo2 + 2Fc2)/3 |
1460 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C15H15NO2 | V = 1250.9 (2) Å3 |
Mr = 241.28 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.7829 (4) Å | µ = 0.09 mm−1 |
b = 12.7379 (13) Å | T = 296 K |
c = 20.532 (2) Å | 0.80 × 0.70 × 0.46 mm |
Stoe IPDSII diffractometer | 1460 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 787 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.994 | Rint = 0.129 |
11194 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 0.79 | Δρmax = 0.13 e Å−3 |
1460 reflections | Δρmin = −0.15 e Å−3 |
164 parameters |
x | y | z | Uiso*/Ueq | ||
N1 | 0.0147 (6) | 0.98344 (19) | 0.15542 (13) | 0.0447 (7) | |
O1 | −0.3647 (5) | 1.11069 (18) | 0.19932 (10) | 0.0582 (8) | |
H1 | −0.2500 | 1.0866 | 0.1737 | 0.087* | |
O2 | 0.1874 (5) | 1.20510 (16) | 0.01226 (10) | 0.0573 (7) | |
H2A | 0.3534 | 1.2131 | 0.0036 | 0.086* | |
C7 | 0.0035 (8) | 0.9353 (3) | 0.21002 (16) | 0.0485 (9) | |
H7 | 0.1295 | 0.8811 | 0.2179 | 0.058* | |
C15 | 0.1614 (8) | 1.1426 (2) | 0.06926 (15) | 0.0547 (11) | |
H15A | −0.0352 | 1.1359 | 0.0801 | 0.066* | |
H15B | 0.2531 | 1.1782 | 0.1051 | 0.066* | |
C9 | −0.2145 (9) | 0.9028 (3) | 0.31711 (16) | 0.0616 (11) | |
H9 | −0.0983 | 0.8450 | 0.3227 | 0.074* | |
C8 | −0.1973 (7) | 0.9619 (3) | 0.25972 (15) | 0.0436 (8) | |
C12 | −0.5574 (8) | 1.0792 (3) | 0.30303 (17) | 0.0509 (10) | |
C11 | −0.5665 (9) | 1.0168 (3) | 0.35773 (18) | 0.0632 (12) | |
H11 | −0.6897 | 1.0344 | 0.3910 | 0.076* | |
C6 | 0.2859 (7) | 1.0336 (2) | 0.06216 (15) | 0.0413 (8) | |
C1 | 0.2078 (7) | 0.9556 (2) | 0.10665 (15) | 0.0431 (8) | |
C13 | −0.3729 (7) | 1.0500 (3) | 0.25363 (16) | 0.0448 (9) | |
C5 | 0.4738 (8) | 1.0091 (3) | 0.01373 (16) | 0.0519 (9) | |
H5 | 0.5264 | 1.0610 | −0.0157 | 0.062* | |
C4 | 0.5866 (8) | 0.9100 (3) | 0.00754 (18) | 0.0568 (10) | |
H4 | 0.7146 | 0.8955 | −0.0253 | 0.068* | |
C2 | 0.3168 (8) | 0.8544 (3) | 0.09890 (18) | 0.0565 (10) | |
H2 | 0.2597 | 0.8010 | 0.1268 | 0.068* | |
C10 | −0.3997 (9) | 0.9290 (3) | 0.36505 (17) | 0.0668 (12) | |
H10 | −0.4134 | 0.8880 | 0.4024 | 0.080* | |
C14 | −0.7375 (9) | 1.1733 (3) | 0.29493 (19) | 0.0725 (12) | |
H14A | −0.8577 | 1.1803 | 0.3321 | 0.109* | |
H14B | −0.8489 | 1.1658 | 0.2563 | 0.109* | |
H14C | −0.6222 | 1.2347 | 0.2911 | 0.109* | |
C3 | 0.5070 (9) | 0.8330 (3) | 0.05063 (17) | 0.0609 (10) | |
H3 | 0.5825 | 0.7660 | 0.0470 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0486 (17) | 0.0428 (17) | 0.0428 (15) | −0.0050 (15) | 0.0044 (16) | 0.0048 (14) |
O1 | 0.0690 (19) | 0.0568 (15) | 0.0487 (14) | 0.0052 (13) | 0.0006 (13) | 0.0111 (12) |
O2 | 0.0561 (16) | 0.0578 (14) | 0.0579 (14) | 0.0031 (13) | 0.0006 (15) | 0.0247 (13) |
C7 | 0.047 (2) | 0.040 (2) | 0.059 (2) | −0.0056 (19) | −0.002 (2) | 0.0025 (17) |
C15 | 0.067 (3) | 0.051 (2) | 0.046 (2) | 0.005 (2) | 0.002 (2) | 0.0148 (17) |
C9 | 0.082 (3) | 0.051 (2) | 0.052 (2) | −0.009 (2) | −0.005 (2) | 0.011 (2) |
C8 | 0.046 (2) | 0.044 (2) | 0.0408 (19) | −0.0072 (19) | −0.0001 (18) | 0.0064 (17) |
C12 | 0.049 (3) | 0.056 (2) | 0.048 (2) | −0.007 (2) | −0.002 (2) | −0.0088 (19) |
C11 | 0.062 (3) | 0.080 (3) | 0.048 (2) | −0.011 (3) | 0.008 (2) | −0.009 (2) |
C6 | 0.041 (2) | 0.044 (2) | 0.0385 (18) | −0.0017 (18) | −0.0012 (17) | 0.0007 (16) |
C1 | 0.043 (2) | 0.042 (2) | 0.0440 (19) | −0.0018 (19) | −0.0028 (18) | 0.0028 (16) |
C13 | 0.045 (2) | 0.050 (2) | 0.0393 (18) | −0.0083 (19) | −0.0022 (18) | 0.0036 (18) |
C5 | 0.057 (2) | 0.054 (2) | 0.044 (2) | −0.003 (2) | 0.004 (2) | 0.0060 (17) |
C4 | 0.059 (3) | 0.057 (2) | 0.055 (2) | 0.002 (2) | 0.010 (2) | −0.009 (2) |
C2 | 0.065 (3) | 0.041 (2) | 0.064 (2) | −0.002 (2) | 0.006 (2) | 0.0025 (18) |
C10 | 0.080 (3) | 0.077 (3) | 0.043 (2) | −0.020 (3) | 0.004 (2) | 0.014 (2) |
C14 | 0.066 (3) | 0.068 (3) | 0.083 (3) | 0.008 (2) | 0.001 (3) | −0.016 (2) |
C3 | 0.067 (3) | 0.046 (2) | 0.069 (2) | 0.000 (2) | 0.005 (3) | −0.007 (2) |
N1—C7 | 1.279 (4) | C12—C14 | 1.485 (5) |
N1—C1 | 1.408 (4) | C11—C10 | 1.382 (5) |
O1—C13 | 1.357 (4) | C11—H11 | 0.9300 |
O1—H1 | 0.8200 | C6—C5 | 1.376 (4) |
O2—C15 | 1.421 (3) | C6—C1 | 1.400 (4) |
O2—H2A | 0.8200 | C1—C2 | 1.399 (5) |
C7—C8 | 1.442 (4) | C5—C4 | 1.378 (5) |
C7—H7 | 0.9300 | C5—H5 | 0.9300 |
C15—C6 | 1.517 (4) | C4—C3 | 1.375 (5) |
C15—H15A | 0.9700 | C4—H4 | 0.9300 |
C15—H15B | 0.9700 | C2—C3 | 1.373 (5) |
C9—C10 | 1.365 (5) | C2—H2 | 0.9300 |
C9—C8 | 1.400 (4) | C10—H10 | 0.9300 |
C9—H9 | 0.9300 | C14—H14A | 0.9600 |
C8—C13 | 1.408 (4) | C14—H14B | 0.9600 |
C12—C11 | 1.377 (5) | C14—H14C | 0.9600 |
C12—C13 | 1.395 (4) | C3—H3 | 0.9300 |
C7—N1—C1 | 122.0 (3) | C2—C1—C6 | 118.7 (3) |
C13—O1—H1 | 109.5 | C2—C1—N1 | 123.9 (3) |
C15—O2—H2A | 109.5 | C6—C1—N1 | 117.4 (3) |
N1—C7—C8 | 122.4 (3) | O1—C13—C12 | 117.6 (3) |
N1—C7—H7 | 118.8 | O1—C13—C8 | 120.7 (3) |
C8—C7—H7 | 118.8 | C12—C13—C8 | 121.7 (3) |
O2—C15—C6 | 113.5 (3) | C6—C5—C4 | 122.0 (3) |
O2—C15—H15A | 108.9 | C6—C5—H5 | 119.0 |
C6—C15—H15A | 108.9 | C4—C5—H5 | 119.0 |
O2—C15—H15B | 108.9 | C3—C4—C5 | 119.1 (4) |
C6—C15—H15B | 108.9 | C3—C4—H4 | 120.5 |
H15A—C15—H15B | 107.7 | C5—C4—H4 | 120.5 |
C10—C9—C8 | 120.9 (4) | C3—C2—C1 | 120.8 (3) |
C10—C9—H9 | 119.5 | C3—C2—H2 | 119.6 |
C8—C9—H9 | 119.5 | C1—C2—H2 | 119.6 |
C9—C8—C13 | 117.9 (3) | C9—C10—C11 | 119.6 (4) |
C9—C8—C7 | 120.6 (3) | C9—C10—H10 | 120.2 |
C13—C8—C7 | 121.5 (3) | C11—C10—H10 | 120.2 |
C11—C12—C13 | 117.3 (4) | C12—C14—H14A | 109.5 |
C11—C12—C14 | 122.6 (4) | C12—C14—H14B | 109.5 |
C13—C12—C14 | 120.0 (3) | H14A—C14—H14B | 109.5 |
C12—C11—C10 | 122.5 (4) | C12—C14—H14C | 109.5 |
C12—C11—H11 | 118.7 | H14A—C14—H14C | 109.5 |
C10—C11—H11 | 118.7 | H14B—C14—H14C | 109.5 |
C5—C6—C1 | 119.0 (3) | C2—C3—C4 | 120.4 (4) |
C5—C6—C15 | 122.2 (3) | C2—C3—H3 | 119.8 |
C1—C6—C15 | 118.8 (3) | C4—C3—H3 | 119.8 |
C1—N1—C7—C8 | −178.7 (3) | C14—C12—C13—O1 | 0.4 (5) |
C10—C9—C8—C13 | 1.2 (5) | C11—C12—C13—C8 | −1.5 (5) |
C10—C9—C8—C7 | 178.5 (3) | C14—C12—C13—C8 | 179.5 (3) |
N1—C7—C8—C9 | 175.9 (3) | C9—C8—C13—O1 | 179.6 (3) |
N1—C7—C8—C13 | −7.0 (5) | C7—C8—C13—O1 | 2.3 (4) |
C13—C12—C11—C10 | 0.7 (6) | C9—C8—C13—C12 | 0.6 (5) |
C14—C12—C11—C10 | 179.7 (4) | C7—C8—C13—C12 | −176.7 (3) |
O2—C15—C6—C5 | 17.9 (5) | C1—C6—C5—C4 | 0.3 (5) |
O2—C15—C6—C1 | −162.4 (3) | C15—C6—C5—C4 | 179.9 (3) |
C5—C6—C1—C2 | −2.1 (5) | C6—C5—C4—C3 | 0.6 (6) |
C15—C6—C1—C2 | 178.2 (3) | C6—C1—C2—C3 | 3.1 (5) |
C5—C6—C1—N1 | −179.9 (3) | N1—C1—C2—C3 | −179.3 (3) |
C15—C6—C1—N1 | 0.5 (4) | C8—C9—C10—C11 | −2.0 (6) |
C7—N1—C1—C2 | 27.9 (5) | C12—C11—C10—C9 | 1.0 (6) |
C7—N1—C1—C6 | −154.5 (3) | C1—C2—C3—C4 | −2.2 (6) |
C11—C12—C13—O1 | 179.4 (3) | C5—C4—C3—C2 | 0.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.86 | 2.595 (4) | 148 |
O2—H2A···O2i | 0.82 | 1.93 | 2.6983 (18) | 155 |
Symmetry code: (i) x+1/2, −y+5/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO2 |
Mr | 241.28 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 4.7829 (4), 12.7379 (13), 20.532 (2) |
V (Å3) | 1250.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.80 × 0.70 × 0.46 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.958, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11194, 1460, 787 |
Rint | 0.129 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.085, 0.79 |
No. of reflections | 1460 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.15 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.86 | 2.595 (4) | 148.0 |
O2—H2A···O2i | 0.82 | 1.93 | 2.6983 (18) | 154.5 |
Symmetry code: (i) x+1/2, −y+5/2, −z. |
In this paper we present the crystal and molecular structures of a Schiff base, C15H15NO2. Recently, Schiff bases have been widely investigated for their properties and applications in different fields, such as catalysis and materials chemistry (Sabater et al., 2001; Di Bella, 2001). Schiff bases derived from 2-hydroxy-1-naphthaldehyde with various alkyl or aryl N-substituents, apart from excellent donor abilities, exhibit interesting photo- and thermo-chromic features. There are two types of intramolecular hydrogen bonds in Schiff bases, which may be stabilized in keto–amine (N—H···O hydrogen bond) or phenol–imine (N···H—O hydrogen bond) tautomeric forms. The present X-ray investigation shows that the title compound exists in the phenol–imine form (Fig. 1).
The C1—N1 and C7—C8 bond lengths are 1.408 (4) and 1.442 (4) Å, respectively, and agree with the corresponding distances in (E)-2-[4-(dimethylamino)phenyliminomethyl]-6-methylphenol [1.412 (2) and 1.441 (3) Å; Gül et al., 2007]. The C7═N1 and O1—C13 bond lengths are 1.279 (4) and 1.357 (4) Å, respectively, and agree with the corresponding distances in 2-[2-(hydroxymethyl)phenyliminomethyl]phenol [1.275 (2) and 1.354 (2) Å; Ersanlı et al., 2004]. Fig.1 also shows a strong intramolecular hydrogen bond, O1—H1···N1, describing a S(6) motif. Atom O2 in the asymmetric unit acts as hydrogen–bond donor, via H2A, connecting this molecule to O2 in a symmetry related molecule at (x + 1/2, -y + 5/2, -z), forming a C(2) chain running parallel to the [100] direction (Fig. 2).