organic compounds
6,6′-Diethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol–ethanol–water (1/1/1)
aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
The title bis-Schiff base compound, C26H28N2O4·C2H6O·H2O, crystallizes as an ethanol and water solvate. Strong intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs. The water H atoms form bifurcated O—H⋯(O,O) intermolecular hydrogen bonds with the O atoms of the hydroxyl and ethoxy groups with R12(5) ring motifs, which may, in part, influence the molecular configuration. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base molecule are 5.64 (8) and 44.78 (9)°. The is further stabilized by intermolecular C—H⋯O and π–π interactions [centroid–centroid distances = 3.6139 (11)–3.7993 (11) Å].
Related literature
For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see, for example: Cakir et al. (2002); Eltayeb et al. (2007a,b); Karabıyık et al. (2007); Fun & Kia (2008); Fun, Kargar & Kia (2008); Fun, Kia & Kargar (2008). For applications of Schiff base ligands, see, for example: Hajioudis et al. (1987); Granovski et al. (1993); Dao et al. (2000); Shahrokhian et al. (2000); Eltayeb & Ahmed (2005a,b); Fakhari et al. (2005); Karthikeyan et al. (2006); Sriram et al. (2006). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809008903/lh2786sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809008903/lh2786Isup2.hkl
The title compound was synthesized by adding 3-ethoxy-salicylaldehyde (4 mmol) to a solution of 4,5-dimethyl-o-phenylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray
were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.H atoms of the hydroxy groups of the Schiff base and ethanol were positioned by a freely rotating O—H bond, see Table 1. The hydrogen of the water molecule were located from the difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and refined as a riding model approximation. A rotating group model was used for the methyl groups.
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Intra- and intermolecular hydrogen bonds are drawn as dashed lines. |
C26H28N2O4·C2H6O·H2O | F(000) = 1064 |
Mr = 496.59 | Dx = 1.270 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4281 reflections |
a = 9.5095 (5) Å | θ = 2.3–27.2° |
b = 25.6633 (12) Å | µ = 0.09 mm−1 |
c = 10.7766 (5) Å | T = 100 K |
β = 99.177 (2)° | Plate, orange |
V = 2596.3 (2) Å3 | 0.45 × 0.12 × 0.02 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 7595 independent reflections |
Radiation source: fine-focus sealed tube | 4303 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
ϕ and ω scans | θmax = 30.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −13→13 |
Tmin = 0.961, Tmax = 0.999 | k = −36→32 |
32813 measured reflections | l = −14→15 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0637P)2 + 0.5228P] where P = (Fo2 + 2Fc2)/3 |
7595 reflections | (Δ/σ)max < 0.001 |
341 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
C26H28N2O4·C2H6O·H2O | V = 2596.3 (2) Å3 |
Mr = 496.59 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.5095 (5) Å | µ = 0.09 mm−1 |
b = 25.6633 (12) Å | T = 100 K |
c = 10.7766 (5) Å | 0.45 × 0.12 × 0.02 mm |
β = 99.177 (2)° |
Bruker SMART APEXII CCD area-detector diffractometer | 7595 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4303 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.999 | Rint = 0.068 |
32813 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.38 e Å−3 |
7595 reflections | Δρmin = −0.51 e Å−3 |
341 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.06040 (14) | 0.16561 (5) | 0.35336 (13) | 0.0257 (3) | |
H1 | 0.0253 | 0.1707 | 0.3841 | 0.039* | |
O2 | 0.13555 (14) | 0.07045 (5) | 0.28857 (12) | 0.0261 (3) | |
H2 | 0.1782 | 0.0973 | 0.3193 | 0.039* | |
O3 | −0.33019 (13) | 0.16242 (5) | 0.25794 (12) | 0.0250 (3) | |
O4 | −0.00004 (14) | −0.01584 (5) | 0.22724 (12) | 0.0276 (3) | |
O5 | 0.1829 (2) | 0.38301 (7) | 0.43926 (18) | 0.0696 (7) | |
H5 | 0.2336 | 0.3938 | 0.5052 | 0.104* | |
N1 | 0.16852 (16) | 0.21898 (6) | 0.42494 (13) | 0.0202 (3) | |
N2 | 0.30447 (16) | 0.12535 (6) | 0.45335 (14) | 0.0221 (4) | |
C1 | −0.12615 (19) | 0.21183 (7) | 0.32673 (16) | 0.0195 (4) | |
C2 | −0.2720 (2) | 0.21128 (7) | 0.27477 (17) | 0.0212 (4) | |
C3 | −0.3428 (2) | 0.25763 (8) | 0.24528 (17) | 0.0239 (4) | |
H3A | −0.4410 | 0.2573 | 0.2103 | 0.029* | |
C4 | −0.2710 (2) | 0.30517 (8) | 0.26650 (18) | 0.0271 (5) | |
H4A | −0.3207 | 0.3369 | 0.2456 | 0.032* | |
C5 | −0.1292 (2) | 0.30622 (8) | 0.31737 (17) | 0.0241 (4) | |
H5A | −0.0812 | 0.3387 | 0.3319 | 0.029* | |
C6 | −0.0546 (2) | 0.25953 (7) | 0.34807 (16) | 0.0197 (4) | |
C7 | 0.0960 (2) | 0.26133 (8) | 0.39833 (16) | 0.0216 (4) | |
H7A | 0.1422 | 0.2941 | 0.4120 | 0.026* | |
C8 | 0.31619 (19) | 0.21948 (7) | 0.47186 (16) | 0.0195 (4) | |
C9 | 0.3962 (2) | 0.26478 (8) | 0.50515 (17) | 0.0222 (4) | |
H9A | 0.3501 | 0.2977 | 0.4944 | 0.027* | |
C10 | 0.5406 (2) | 0.26294 (7) | 0.55340 (16) | 0.0212 (4) | |
C11 | 0.6084 (2) | 0.21406 (8) | 0.56871 (17) | 0.0216 (4) | |
C12 | 0.5301 (2) | 0.16936 (8) | 0.53558 (16) | 0.0222 (4) | |
H12A | 0.5768 | 0.1365 | 0.5447 | 0.027* | |
C13 | 0.3845 (2) | 0.17112 (7) | 0.48914 (16) | 0.0207 (4) | |
C14 | 0.3273 (2) | 0.08414 (7) | 0.52055 (17) | 0.0236 (4) | |
H14A | 0.3939 | 0.0857 | 0.5962 | 0.028* | |
C15 | 0.2554 (2) | 0.03506 (8) | 0.48551 (17) | 0.0229 (4) | |
C16 | 0.2757 (2) | −0.00817 (8) | 0.56692 (18) | 0.0279 (5) | |
H16A | 0.3398 | −0.0056 | 0.6439 | 0.033* | |
C17 | 0.2041 (2) | −0.05394 (8) | 0.53627 (19) | 0.0287 (5) | |
H17A | 0.2191 | −0.0829 | 0.5917 | 0.034* | |
C18 | 0.1087 (2) | −0.05798 (8) | 0.42326 (19) | 0.0270 (4) | |
H18A | 0.0579 | −0.0895 | 0.4029 | 0.032* | |
C19 | 0.0884 (2) | −0.01644 (7) | 0.34162 (17) | 0.0232 (4) | |
C20 | 0.16074 (19) | 0.03062 (7) | 0.37184 (17) | 0.0208 (4) | |
C21 | −0.47745 (19) | 0.15886 (8) | 0.20175 (18) | 0.0262 (4) | |
H21A | −0.4913 | 0.1729 | 0.1151 | 0.031* | |
H21B | −0.5377 | 0.1790 | 0.2515 | 0.031* | |
C22 | −0.5166 (2) | 0.10202 (8) | 0.20022 (19) | 0.0310 (5) | |
H22A | −0.6166 | 0.0978 | 0.1622 | 0.047* | |
H22B | −0.5027 | 0.0887 | 0.2865 | 0.047* | |
H22C | −0.4559 | 0.0826 | 0.1510 | 0.047* | |
C23 | −0.0850 (2) | −0.06146 (8) | 0.1942 (2) | 0.0305 (5) | |
H23A | −0.1449 | −0.0689 | 0.2592 | 0.037* | |
H23B | −0.0231 | −0.0920 | 0.1869 | 0.037* | |
C24 | −0.1771 (3) | −0.05042 (9) | 0.0699 (2) | 0.0410 (6) | |
H24A | −0.2390 | −0.0804 | 0.0451 | 0.061* | |
H24B | −0.1166 | −0.0441 | 0.0059 | 0.061* | |
H24C | −0.2358 | −0.0196 | 0.0778 | 0.061* | |
C25 | 0.6220 (2) | 0.31263 (8) | 0.58803 (19) | 0.0276 (5) | |
H25A | 0.5559 | 0.3422 | 0.5782 | 0.041* | |
H25B | 0.6935 | 0.3174 | 0.5328 | 0.041* | |
H25C | 0.6694 | 0.3106 | 0.6756 | 0.041* | |
C26 | 0.7651 (2) | 0.21015 (8) | 0.62075 (18) | 0.0279 (5) | |
H26A | 0.7960 | 0.1738 | 0.6173 | 0.042* | |
H26B | 0.7816 | 0.2222 | 0.7082 | 0.042* | |
H26C | 0.8195 | 0.2319 | 0.5705 | 0.042* | |
C27 | 0.0836 (4) | 0.45876 (12) | 0.3369 (3) | 0.0799 (11) | |
H27A | 0.0918 | 0.4816 | 0.2655 | 0.120* | |
H27B | 0.0995 | 0.4791 | 0.4148 | 0.120* | |
H27C | −0.0118 | 0.4433 | 0.3258 | 0.120* | |
C28 | 0.1892 (3) | 0.41771 (13) | 0.3437 (2) | 0.0575 (8) | |
H28A | 0.1756 | 0.3986 | 0.2629 | 0.069* | |
H28B | 0.2852 | 0.4337 | 0.3553 | 0.069* | |
O1W | 0.84548 (19) | 0.08448 (7) | 0.14875 (16) | 0.0412 (4) | |
H1W1 | 0.920 (3) | 0.0656 (11) | 0.169 (3) | 0.064 (9)* | |
H2W1 | 0.855 (3) | 0.1065 (13) | 0.199 (3) | 0.076 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0167 (6) | 0.0236 (7) | 0.0347 (8) | 0.0002 (6) | −0.0026 (6) | 0.0009 (6) |
O2 | 0.0295 (8) | 0.0200 (7) | 0.0262 (7) | −0.0036 (6) | −0.0031 (6) | 0.0021 (6) |
O3 | 0.0155 (6) | 0.0262 (8) | 0.0318 (7) | 0.0000 (6) | −0.0008 (5) | −0.0009 (6) |
O4 | 0.0285 (7) | 0.0219 (7) | 0.0291 (7) | −0.0042 (6) | −0.0058 (6) | −0.0017 (6) |
O5 | 0.0928 (16) | 0.0370 (11) | 0.0628 (13) | −0.0105 (10) | −0.0368 (11) | 0.0001 (9) |
N1 | 0.0185 (8) | 0.0257 (9) | 0.0163 (7) | −0.0007 (7) | 0.0022 (6) | −0.0002 (6) |
N2 | 0.0210 (8) | 0.0214 (9) | 0.0230 (8) | −0.0016 (7) | 0.0012 (7) | −0.0028 (6) |
C1 | 0.0194 (9) | 0.0234 (10) | 0.0158 (8) | 0.0027 (8) | 0.0030 (7) | −0.0003 (7) |
C2 | 0.0195 (9) | 0.0257 (11) | 0.0185 (9) | 0.0005 (8) | 0.0035 (7) | −0.0015 (7) |
C3 | 0.0197 (9) | 0.0326 (11) | 0.0191 (9) | 0.0035 (8) | 0.0027 (7) | 0.0008 (8) |
C4 | 0.0274 (11) | 0.0256 (11) | 0.0283 (10) | 0.0083 (9) | 0.0048 (8) | 0.0031 (8) |
C5 | 0.0267 (10) | 0.0220 (10) | 0.0240 (9) | 0.0011 (8) | 0.0054 (8) | −0.0004 (8) |
C6 | 0.0208 (9) | 0.0255 (10) | 0.0136 (8) | 0.0018 (8) | 0.0046 (7) | −0.0007 (7) |
C7 | 0.0229 (10) | 0.0238 (10) | 0.0182 (9) | −0.0029 (8) | 0.0036 (7) | −0.0008 (7) |
C8 | 0.0196 (9) | 0.0248 (10) | 0.0141 (8) | −0.0014 (8) | 0.0030 (7) | −0.0007 (7) |
C9 | 0.0248 (10) | 0.0229 (10) | 0.0192 (9) | −0.0010 (8) | 0.0042 (8) | −0.0009 (7) |
C10 | 0.0234 (9) | 0.0262 (10) | 0.0146 (8) | −0.0059 (8) | 0.0050 (7) | −0.0012 (7) |
C11 | 0.0190 (9) | 0.0297 (11) | 0.0172 (8) | −0.0036 (8) | 0.0056 (7) | −0.0021 (8) |
C12 | 0.0210 (9) | 0.0255 (10) | 0.0198 (9) | 0.0018 (8) | 0.0022 (7) | −0.0006 (8) |
C13 | 0.0229 (9) | 0.0233 (10) | 0.0162 (8) | −0.0014 (8) | 0.0039 (7) | −0.0020 (7) |
C14 | 0.0196 (9) | 0.0291 (11) | 0.0211 (9) | −0.0006 (8) | −0.0005 (8) | −0.0018 (8) |
C15 | 0.0198 (9) | 0.0241 (10) | 0.0243 (9) | −0.0004 (8) | 0.0018 (8) | −0.0009 (8) |
C16 | 0.0274 (10) | 0.0277 (11) | 0.0269 (10) | 0.0032 (9) | −0.0005 (8) | 0.0040 (8) |
C17 | 0.0295 (11) | 0.0252 (11) | 0.0302 (10) | 0.0032 (9) | 0.0015 (9) | 0.0052 (8) |
C18 | 0.0255 (10) | 0.0203 (10) | 0.0348 (11) | −0.0004 (8) | 0.0038 (9) | −0.0005 (8) |
C19 | 0.0199 (9) | 0.0239 (10) | 0.0253 (9) | 0.0014 (8) | 0.0015 (8) | −0.0026 (8) |
C20 | 0.0196 (9) | 0.0191 (10) | 0.0238 (9) | 0.0010 (8) | 0.0039 (8) | −0.0007 (7) |
C21 | 0.0162 (9) | 0.0386 (12) | 0.0226 (9) | −0.0009 (9) | −0.0009 (7) | −0.0001 (8) |
C22 | 0.0208 (10) | 0.0402 (13) | 0.0317 (11) | −0.0052 (9) | 0.0030 (9) | −0.0031 (9) |
C23 | 0.0278 (11) | 0.0227 (11) | 0.0389 (11) | −0.0052 (9) | −0.0009 (9) | −0.0054 (9) |
C24 | 0.0407 (13) | 0.0367 (13) | 0.0400 (12) | −0.0085 (11) | −0.0106 (11) | −0.0076 (10) |
C25 | 0.0259 (10) | 0.0299 (11) | 0.0268 (10) | −0.0085 (9) | 0.0033 (8) | −0.0021 (8) |
C26 | 0.0209 (10) | 0.0366 (12) | 0.0256 (10) | −0.0027 (9) | 0.0024 (8) | −0.0043 (9) |
C27 | 0.081 (2) | 0.0466 (18) | 0.093 (2) | −0.0021 (17) | −0.044 (2) | −0.0018 (16) |
C28 | 0.0434 (15) | 0.096 (2) | 0.0340 (13) | −0.0122 (16) | 0.0109 (12) | −0.0044 (14) |
O1W | 0.0394 (10) | 0.0386 (10) | 0.0406 (9) | 0.0105 (8) | −0.0088 (8) | −0.0115 (8) |
O1—C1 | 1.350 (2) | C14—H14A | 0.9500 |
O1—H1 | 0.8400 | C15—C20 | 1.404 (2) |
O2—C20 | 1.356 (2) | C15—C16 | 1.409 (3) |
O2—H2 | 0.8400 | C16—C17 | 1.372 (3) |
O3—C2 | 1.371 (2) | C16—H16A | 0.9500 |
O3—C21 | 1.437 (2) | C17—C18 | 1.401 (3) |
O4—C19 | 1.377 (2) | C17—H17A | 0.9500 |
O4—C23 | 1.435 (2) | C18—C19 | 1.376 (3) |
O5—C28 | 1.370 (3) | C18—H18A | 0.9500 |
O5—H5 | 0.8400 | C19—C20 | 1.403 (3) |
N1—C7 | 1.295 (2) | C21—C22 | 1.505 (3) |
N1—C8 | 1.415 (2) | C21—H21A | 0.9900 |
N2—C14 | 1.281 (2) | C21—H21B | 0.9900 |
N2—C13 | 1.419 (2) | C22—H22A | 0.9800 |
C1—C6 | 1.402 (3) | C22—H22B | 0.9800 |
C1—C2 | 1.411 (2) | C22—H22C | 0.9800 |
C2—C3 | 1.379 (3) | C23—C24 | 1.506 (3) |
C3—C4 | 1.399 (3) | C23—H23A | 0.9900 |
C3—H3A | 0.9500 | C23—H23B | 0.9900 |
C4—C5 | 1.373 (3) | C24—H24A | 0.9800 |
C4—H4A | 0.9500 | C24—H24B | 0.9800 |
C5—C6 | 1.405 (3) | C24—H24C | 0.9800 |
C5—H5A | 0.9500 | C25—H25A | 0.9800 |
C6—C7 | 1.448 (3) | C25—H25B | 0.9800 |
C7—H7A | 0.9500 | C25—H25C | 0.9800 |
C8—C13 | 1.399 (3) | C26—H26A | 0.9800 |
C8—C9 | 1.404 (3) | C26—H26B | 0.9800 |
C9—C10 | 1.390 (3) | C26—H26C | 0.9800 |
C9—H9A | 0.9500 | C27—C28 | 1.449 (4) |
C10—C11 | 1.408 (3) | C27—H27A | 0.9800 |
C10—C25 | 1.507 (3) | C27—H27B | 0.9800 |
C11—C12 | 1.383 (3) | C27—H27C | 0.9800 |
C11—C26 | 1.510 (3) | C28—H28A | 0.9900 |
C12—C13 | 1.396 (3) | C28—H28B | 0.9900 |
C12—H12A | 0.9500 | O1W—H1W1 | 0.86 (3) |
C14—C15 | 1.454 (3) | O1W—H2W1 | 0.78 (3) |
C1—O1—H1 | 109.5 | C19—C18—C17 | 120.25 (18) |
C20—O2—H2 | 109.5 | C19—C18—H18A | 119.9 |
C2—O3—C21 | 117.35 (14) | C17—C18—H18A | 119.9 |
C19—O4—C23 | 116.90 (15) | C18—C19—O4 | 125.77 (17) |
C28—O5—H5 | 109.5 | C18—C19—C20 | 120.33 (17) |
C7—N1—C8 | 122.35 (16) | O4—C19—C20 | 113.90 (16) |
C14—N2—C13 | 119.64 (15) | O2—C20—C19 | 117.85 (16) |
O1—C1—C6 | 122.41 (16) | O2—C20—C15 | 122.49 (17) |
O1—C1—C2 | 117.93 (16) | C19—C20—C15 | 119.67 (17) |
C6—C1—C2 | 119.66 (17) | O3—C21—C22 | 106.80 (16) |
O3—C2—C3 | 125.94 (17) | O3—C21—H21A | 110.4 |
O3—C2—C1 | 114.33 (16) | C22—C21—H21A | 110.4 |
C3—C2—C1 | 119.73 (18) | O3—C21—H21B | 110.4 |
C2—C3—C4 | 120.48 (17) | C22—C21—H21B | 110.4 |
C2—C3—H3A | 119.8 | H21A—C21—H21B | 108.6 |
C4—C3—H3A | 119.8 | C21—C22—H22A | 109.5 |
C5—C4—C3 | 120.33 (18) | C21—C22—H22B | 109.5 |
C5—C4—H4A | 119.8 | H22A—C22—H22B | 109.5 |
C3—C4—H4A | 119.8 | C21—C22—H22C | 109.5 |
C4—C5—C6 | 120.30 (18) | H22A—C22—H22C | 109.5 |
C4—C5—H5A | 119.9 | H22B—C22—H22C | 109.5 |
C6—C5—H5A | 119.9 | O4—C23—C24 | 107.00 (17) |
C1—C6—C5 | 119.50 (17) | O4—C23—H23A | 110.3 |
C1—C6—C7 | 120.96 (17) | C24—C23—H23A | 110.3 |
C5—C6—C7 | 119.52 (17) | O4—C23—H23B | 110.3 |
N1—C7—C6 | 121.07 (17) | C24—C23—H23B | 110.3 |
N1—C7—H7A | 119.5 | H23A—C23—H23B | 108.6 |
C6—C7—H7A | 119.5 | C23—C24—H24A | 109.5 |
C13—C8—C9 | 118.63 (17) | C23—C24—H24B | 109.5 |
C13—C8—N1 | 116.93 (16) | H24A—C24—H24B | 109.5 |
C9—C8—N1 | 124.41 (17) | C23—C24—H24C | 109.5 |
C10—C9—C8 | 122.02 (18) | H24A—C24—H24C | 109.5 |
C10—C9—H9A | 119.0 | H24B—C24—H24C | 109.5 |
C8—C9—H9A | 119.0 | C10—C25—H25A | 109.5 |
C9—C10—C11 | 118.72 (17) | C10—C25—H25B | 109.5 |
C9—C10—C25 | 120.09 (18) | H25A—C25—H25B | 109.5 |
C11—C10—C25 | 121.19 (17) | C10—C25—H25C | 109.5 |
C12—C11—C10 | 119.47 (17) | H25A—C25—H25C | 109.5 |
C12—C11—C26 | 119.94 (18) | H25B—C25—H25C | 109.5 |
C10—C11—C26 | 120.59 (17) | C11—C26—H26A | 109.5 |
C11—C12—C13 | 121.84 (18) | C11—C26—H26B | 109.5 |
C11—C12—H12A | 119.1 | H26A—C26—H26B | 109.5 |
C13—C12—H12A | 119.1 | C11—C26—H26C | 109.5 |
C12—C13—C8 | 119.30 (17) | H26A—C26—H26C | 109.5 |
C12—C13—N2 | 121.93 (17) | H26B—C26—H26C | 109.5 |
C8—C13—N2 | 118.71 (16) | C28—C27—H27A | 109.5 |
N2—C14—C15 | 122.55 (17) | C28—C27—H27B | 109.5 |
N2—C14—H14A | 118.7 | H27A—C27—H27B | 109.5 |
C15—C14—H14A | 118.7 | C28—C27—H27C | 109.5 |
C20—C15—C16 | 118.99 (17) | H27A—C27—H27C | 109.5 |
C20—C15—C14 | 120.42 (17) | H27B—C27—H27C | 109.5 |
C16—C15—C14 | 120.55 (17) | O5—C28—C27 | 113.5 (3) |
C17—C16—C15 | 120.73 (18) | O5—C28—H28A | 108.9 |
C17—C16—H16A | 119.6 | C27—C28—H28A | 108.9 |
C15—C16—H16A | 119.6 | O5—C28—H28B | 108.9 |
C16—C17—C18 | 120.03 (18) | C27—C28—H28B | 108.9 |
C16—C17—H17A | 120.0 | H28A—C28—H28B | 107.7 |
C18—C17—H17A | 120.0 | H1W1—O1W—H2W1 | 103 (3) |
C21—O3—C2—C3 | 1.6 (3) | C26—C11—C12—C13 | 178.89 (17) |
C21—O3—C2—C1 | −178.13 (16) | C11—C12—C13—C8 | 2.0 (3) |
O1—C1—C2—O3 | 0.3 (2) | C11—C12—C13—N2 | 179.06 (17) |
C6—C1—C2—O3 | 179.82 (16) | C9—C8—C13—C12 | −1.7 (3) |
O1—C1—C2—C3 | −179.47 (16) | N1—C8—C13—C12 | −179.82 (16) |
C6—C1—C2—C3 | 0.1 (3) | C9—C8—C13—N2 | −178.84 (16) |
O3—C2—C3—C4 | −179.69 (17) | N1—C8—C13—N2 | 3.0 (2) |
C1—C2—C3—C4 | 0.0 (3) | C14—N2—C13—C12 | 40.6 (3) |
C2—C3—C4—C5 | −0.2 (3) | C14—N2—C13—C8 | −142.33 (18) |
C3—C4—C5—C6 | 0.3 (3) | C13—N2—C14—C15 | −176.25 (17) |
O1—C1—C6—C5 | 179.54 (16) | N2—C14—C15—C20 | 2.6 (3) |
C2—C1—C6—C5 | 0.0 (3) | N2—C14—C15—C16 | −175.16 (19) |
O1—C1—C6—C7 | 1.1 (3) | C20—C15—C16—C17 | −0.2 (3) |
C2—C1—C6—C7 | −178.44 (17) | C14—C15—C16—C17 | 177.60 (19) |
C4—C5—C6—C1 | −0.2 (3) | C15—C16—C17—C18 | −0.4 (3) |
C4—C5—C6—C7 | 178.27 (18) | C16—C17—C18—C19 | 1.1 (3) |
C8—N1—C7—C6 | 178.76 (16) | C17—C18—C19—O4 | 178.80 (19) |
C1—C6—C7—N1 | 0.0 (3) | C17—C18—C19—C20 | −1.2 (3) |
C5—C6—C7—N1 | −178.43 (17) | C23—O4—C19—C18 | 4.2 (3) |
C7—N1—C8—C13 | −175.89 (16) | C23—O4—C19—C20 | −175.79 (17) |
C7—N1—C8—C9 | 6.1 (3) | C18—C19—C20—O2 | −179.31 (18) |
C13—C8—C9—C10 | 0.6 (3) | O4—C19—C20—O2 | 0.6 (2) |
N1—C8—C9—C10 | 178.60 (17) | C18—C19—C20—C15 | 0.6 (3) |
C8—C9—C10—C11 | 0.2 (3) | O4—C19—C20—C15 | −179.42 (17) |
C8—C9—C10—C25 | −179.88 (17) | C16—C15—C20—O2 | −179.95 (18) |
C9—C10—C11—C12 | 0.0 (3) | C14—C15—C20—O2 | 2.2 (3) |
C25—C10—C11—C12 | −179.86 (17) | C16—C15—C20—C19 | 0.1 (3) |
C9—C10—C11—C26 | 179.99 (17) | C14—C15—C20—C19 | −177.71 (18) |
C25—C10—C11—C26 | 0.1 (3) | C2—O3—C21—C22 | −177.08 (16) |
C10—C11—C12—C13 | −1.2 (3) | C19—O4—C23—C24 | 177.06 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 | 1.84 | 2.584 (2) | 146 |
O1W—H1W1···O2i | 0.86 (3) | 2.24 (3) | 2.947 (2) | 139 (3) |
O1W—H1W1···O4i | 0.86 (3) | 2.28 (3) | 3.018 (2) | 145 (3) |
O2—H2···N2 | 0.84 | 1.87 | 2.609 (2) | 146 |
O1W—H2W1···O1i | 0.78 (3) | 2.30 (3) | 3.061 (2) | 166 (3) |
O1W—H2W1···O3i | 0.78 (3) | 2.43 (3) | 2.967 (2) | 127 (3) |
O5—H5···O1Wii | 0.84 | 1.82 | 2.659 (3) | 179 |
C7—H7A···O5 | 0.95 | 2.33 | 3.242 (3) | 162 |
Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C26H28N2O4·C2H6O·H2O |
Mr | 496.59 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 9.5095 (5), 25.6633 (12), 10.7766 (5) |
β (°) | 99.177 (2) |
V (Å3) | 2596.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.45 × 0.12 × 0.02 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.961, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32813, 7595, 4303 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.160, 1.03 |
No. of reflections | 7595 |
No. of parameters | 341 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.51 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 | 1.84 | 2.584 (2) | 146 |
O1W—H1W1···O2i | 0.86 (3) | 2.24 (3) | 2.947 (2) | 139 (3) |
O1W—H1W1···O4i | 0.86 (3) | 2.28 (3) | 3.018 (2) | 145 (3) |
O2—H2···N2 | 0.84 | 1.87 | 2.609 (2) | 146 |
O1W—H2W1···O1i | 0.78 (3) | 2.30 (3) | 3.061 (2) | 166 (3) |
O1W—H2W1···O3i | 0.78 (3) | 2.43 (3) | 2.967 (2) | 127 (3) |
O5—H5···O1Wii | 0.84 | 1.82 | 2.659 (3) | 179 |
C7—H7A···O5 | 0.95 | 2.33 | 3.242 (3) | 162 |
Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, z+1/2. |
Footnotes
‡Additional correspondance author, e-mail: zsrkk@yahoo.com.
Acknowledgements
HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK and AJ thank PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cakir, O., Elerman, Y. & Elmali, A. (2002). Anal. Sci. 18, 377. Web of Science CSD CrossRef PubMed Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805–813. Web of Science CrossRef PubMed CAS Google Scholar
Eltayeb, N. E. & Ahmed, T. A. (2005a). J. Sci. Technol. 6, 51–59. Google Scholar
Eltayeb, N. E. & Ahmed, T. A. (2005b). Sudan J. Basic Sci. 7, 97–108. Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007a). Acta Cryst. E63, o3094–o3095. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007b). Acta Cryst. E63, o3234–o3235. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fakhari, A. R., Khorrami, A. R. & Naeimi, H. (2005). Talanta, 66, 813–817. Web of Science CrossRef PubMed CAS Google Scholar
Fun, H.-K., Kargar, H. & Kia, R. (2008). Acta Cryst. E64, o1308. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, o1657–o1658. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Kia, R. & Kargar, H. (2008). Acta Cryst. E64, o1335. Web of Science CSD CrossRef IUCr Journals Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. Google Scholar
Hajioudis, E., Vitterakis, M. & Mustakali-Mavridis, I. (1987). Tetrahedron, 43, 1345–1351. Google Scholar
Karabıyık, H., Güzel, B., Aygün, M., Boğa, G. & Büyükgüngör, O. (2007). Acta Cryst. C63, o215–o218. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Shahrokhian, S., Amini, M. K., Kia, R. & Tangestaninejad, S. (2000). Anal. Chem. 72, 956–962. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129. Web of Science CrossRef PubMed CAS Google Scholar
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 bases have received much attention because of their potential applications with some of these compounds exhibiting various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. Although numerous transition-metal complexes of Schiff bases have been structurally characterized (Granovski et al., 1993), relatively few free Schiff bases have been similarly characterized. N-substituted salicylaldimines show photochromism and thermochromism in the solid state. These effects are produced by intramolecular proton transfer associated with a change in the π-electron configuration (Hadjioudis et al. 1987). In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b) such as nickel in some natural food products (Fakhari et al., 2005) or biologically important species (Shahrokhian et al., 2000). As part of a general study of tetradenate and bidentate Schiff bases (Fun, Kargar & Kia 2008; Fun, Kia & Kargar 2008), we determined the structure of the title compound.
The asymmetric unit of the title compound, Fig. 1, comprises a Schiff base ligand, an ethanol and a water molecule of crystallization. All bonds lengths agree with standard values (Allen et al., 1987). Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The hydrogen atoms of the water molecule make bifurcated intermolecular hydrogen bonds with the oxygen atoms of the hydroxyl and ethoxy groups with R21(5) ring motifs (Bernstein et al., 1995), which may, in part, influence the molecular configuration (Table 1). The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 5.64 (8) and 44.78 (9)° which shows one of the outer benzene ring is twisted. The crystal structure is further stabilized by intermolecular C—H···O and π-π interactions [Cg1···Cg1iii = 3.6139 (11) Å, (iii) x - 1/2, 1/2 - y, z - 1/2; Cg2···Cg2iv = 3.7993 (11) Å, (iv) -x, -y, z - 1; Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 benzene rings].