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2-[(E)-(4-Methylphenyl)iminomethyl]-6-(morpholin-4-ylmethyl)phenol
aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title compound, C19H22N2O2, the morpholine ring adopts an almost perfect normal chair conformation with puckering parameters QT, θ and φ of 0.5642 (18) Å, 177.32 (17) and φ = 10 (4)°, respectively. The two benzene rings make a dihedral angle of 42.67 (8)° with each other. An intramolecular O—H⋯N hydrogen bond helps to stabilize the molecular conformation. Aromatic C—H⋯π interactions and π–π stacking interactions [centroid–centroid distance = 3.6155 (15) Å] between the benzene rings contribute to the stabilization of the crystal structure.
Related literature
For general background to et al. (2008); Dhar & Taploo (1982
); Emregül et al. (2006
); Jarrahpour & Khalili (2006
); Jarrahpour et al. (2007
); Mladenova et al. (2002
); Przybylski et al. (2009
); Sessler et al. (2006
); Singh et al. (2006
). For a similar structure, see: Akkurt et al. (2008
). For reference structural data, see: Allen et al. (1987
). For see: Cremer & Pople (1975
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002
); program(s) used to solve structure: SIR97 (Altomare et al., 1999
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
); software used to prepare material for publication: WinGX (Farrugia, 1999
).
Supporting information
https://doi.org/10.1107/S1600536810052311/si2317sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052311/si2317Isup2.hkl
Reaction of 2-hydroxy-3-(morpholinomethyl)benzaldehyde with 4-methylaniline in refluxing ethanol gave Schiff base (I) that recrystallized from ethanol to give orange crystals in 85% yield. [mp: 377–379 K]. IR (KBr, cm-1): 1615.2 (C═N), 3170.6–3310.5 (OH). 1H-NMR (250 MHz, CDCl3) δ (p.p.m): 2.30 (Me, s, 3H), 2.51 (CH2, t, 4H, J = 4.5), 3.60 (CH2, s, 2H), 3.69 (CH2, t, 4H, J = 4.5), 6.81–7.38 (m, ArH, 7H), 8.56 (HC═N, s, 1H), 13.68 (OH, s, 1H). 13C-NMR (CDCl3) δ (p.p.m): 21.0 (Me), 53.5 (N—CH2), 56.4 (CH2), 66.8 (O—CH2), 118.5–159.7 (C=C aromatic carbons), 161.3 (C=N).
All H atoms were placed at calculated positions and were treated as riding on their parent atoms with O—H = 0.82 Å, C—H = 0.93 (aromatic), 0.96(methyl) and 0.97 Å (methylene), and with Uiso(H) = 1.5Ueq(O,C) for hydroxy and methyl and Uiso(H) = 1.2Ueq(C) for aromatic, methylene.
Schiff bases, named for Hugo Schiff with the azomethine or imine group (—C═ N—) usually synthesized by condensation of a primary amine and an active carbonyl group under specific conditions. These compounds show a broad range of applications such as corrosion inhibitors (Emregül et al., 2006), catalysts (Sessler et al., 2006), pigments and polymer stabilizers. possess high biological activities including antibacterial (Jarrahpour et al., 2006), antifungal (Singh et al., 2006), antitumor (Mladenova et al., 2002), antimalarial (Przybylski et al., 2009), antiviral (Jarrahpour et al., 2007) and antipyretic properties (Dhar et al., 1982). are also good intermediates for the synthesis of other chemical substances such as 2-azetidinones.
As shown in Fig. 1, the morpholine ring (N2/O2/C16–C19) of the title compound (I) adopts a chair conformation with puckering parameters QT, θ and φ of 0.5642 (18) Å, 177.32 (17) ° and φ = 10 (4) ° (Cremer & Pople (1975). The dihedral angle between the (C1–C6) and (C9–C14) benzene rings in (I) is 42.67 (8)°. The bond lengths exhibit normal values (Allen et al. 1987) and are comparable with those in our similar structure previously published (Akkurt et al., 2008).
The π interaction (Table 1) and a π-π stacking interaction between the C9–C14 benzene rings contribute to the stabilization of the crystal packing [Cg3···Cg3ii(symmetry code ii = 1 - x, 1 - y, -z) = 3.6155 (15) Å, where Cg3 is a centroid of the C9–C14 benzene ring]. Fig. 2 shows the crystal packing of (I) down the a axis.
of (I) is stabilized by intramolecular weak C12—H12···N2 and strong O1—H1···N1 hydrogen bonds (Table 1). In the a C—H···For general background to ═N—), see: Akkurt et al. (2008); Dhar & Taploo (1982); Emregül et al. (2006); Jarrahpour & Khalili (2006); Jarrahpour et al. (2007); Mladenova et al. (2002); Przybylski et al. (2009); Sessler et al. (2006); Singh et al. (2006). For a similar structure, see: Akkurt et al. (2008). For reference structural data, see: Allen et al. (1987). For see: Cremer & Pople (1975).
with an azomethine or imine group (—CData collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C19H22N2O2 | Z = 2 |
Mr = 310.39 | F(000) = 332 |
Triclinic, P1 | Dx = 1.244 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.807 (3) Å | Cell parameters from 2924 reflections |
b = 10.091 (3) Å | θ = 2.2–28.0° |
c = 10.528 (3) Å | µ = 0.08 mm−1 |
α = 99.78 (2)° | T = 296 K |
β = 109.34 (2)° | Prism, yellow |
γ = 115.18 (2)° | 0.53 × 0.40 × 0.23 mm |
V = 828.7 (5) Å3 |
Stoe IPDS 2 diffractometer | 3443 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2894 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.026 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 2.2° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.958, Tmax = 0.982 | l = −13→13 |
15421 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0601P)2 + 0.1054P] where P = (Fo2 + 2Fc2)/3 |
3443 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C19H22N2O2 | γ = 115.18 (2)° |
Mr = 310.39 | V = 828.7 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.807 (3) Å | Mo Kα radiation |
b = 10.091 (3) Å | µ = 0.08 mm−1 |
c = 10.528 (3) Å | T = 296 K |
α = 99.78 (2)° | 0.53 × 0.40 × 0.23 mm |
β = 109.34 (2)° |
Stoe IPDS 2 diffractometer | 3443 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2894 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.982 | Rint = 0.026 |
15421 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.19 e Å−3 |
3443 reflections | Δρmin = −0.17 e Å−3 |
208 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.68415 (12) | 0.65889 (11) | 0.31759 (10) | 0.0605 (3) | |
O2 | 0.25927 (15) | −0.05310 (13) | 0.37129 (14) | 0.0731 (4) | |
N1 | 0.70908 (14) | 0.89705 (12) | 0.23661 (12) | 0.0509 (3) | |
N2 | 0.39377 (13) | 0.18806 (12) | 0.26385 (12) | 0.0470 (3) | |
C1 | 0.80432 (16) | 1.05345 (14) | 0.24513 (14) | 0.0460 (4) | |
C2 | 0.90410 (18) | 1.17249 (16) | 0.38095 (15) | 0.0529 (4) | |
C3 | 1.00285 (17) | 1.32583 (15) | 0.39579 (15) | 0.0541 (4) | |
C4 | 1.00833 (16) | 1.36570 (15) | 0.27667 (15) | 0.0508 (4) | |
C5 | 0.90948 (17) | 1.24557 (15) | 0.14201 (15) | 0.0515 (4) | |
C6 | 0.80862 (16) | 1.09138 (14) | 0.12519 (14) | 0.0492 (4) | |
C7 | 1.1219 (2) | 1.53245 (17) | 0.29286 (19) | 0.0719 (5) | |
C8 | 0.56247 (17) | 0.80217 (15) | 0.13084 (15) | 0.0496 (4) | |
C9 | 0.46275 (16) | 0.63836 (14) | 0.11187 (14) | 0.0464 (4) | |
C10 | 0.52758 (16) | 0.57282 (14) | 0.20561 (13) | 0.0461 (4) | |
C11 | 0.43183 (16) | 0.41315 (14) | 0.18260 (14) | 0.0469 (4) | |
C12 | 0.27222 (17) | 0.32268 (15) | 0.06675 (15) | 0.0503 (4) | |
C13 | 0.20689 (17) | 0.38570 (16) | −0.02683 (15) | 0.0538 (4) | |
C14 | 0.30183 (17) | 0.54185 (16) | −0.00456 (15) | 0.0529 (4) | |
C15 | 0.51246 (18) | 0.34623 (16) | 0.28015 (16) | 0.0565 (4) | |
C16 | 0.48127 (18) | 0.10773 (17) | 0.31696 (16) | 0.0555 (5) | |
C17 | 0.3568 (2) | −0.05472 (17) | 0.29914 (17) | 0.0625 (5) | |
C18 | 0.1757 (2) | 0.0270 (2) | 0.3227 (2) | 0.0783 (7) | |
C19 | 0.2971 (2) | 0.19116 (18) | 0.34212 (18) | 0.0620 (5) | |
H1 | 0.72840 | 0.74990 | 0.32090 | 0.0910* | |
H2 | 0.90420 | 1.14840 | 0.46240 | 0.0630* | |
H3 | 1.06710 | 1.40420 | 0.48720 | 0.0650* | |
H5 | 0.91110 | 1.26940 | 0.06080 | 0.0620* | |
H6 | 0.74370 | 1.01320 | 0.03360 | 0.0590* | |
H7A | 1.23740 | 1.56600 | 0.35230 | 0.0860* | |
H7B | 1.09230 | 1.60030 | 0.33720 | 0.0860* | |
H7C | 1.10810 | 1.53690 | 0.19930 | 0.0860* | |
H8 | 0.51770 | 0.83940 | 0.06320 | 0.0600* | |
H12 | 0.20700 | 0.21690 | 0.05110 | 0.0600* | |
H13 | 0.09940 | 0.32250 | −0.10420 | 0.0650* | |
H14 | 0.25840 | 0.58370 | −0.06780 | 0.0630* | |
H15A | 0.60110 | 0.34430 | 0.25960 | 0.0680* | |
H15B | 0.56460 | 0.41530 | 0.37980 | 0.0680* | |
H16A | 0.56130 | 0.16730 | 0.41820 | 0.0670* | |
H16B | 0.54360 | 0.10120 | 0.26380 | 0.0670* | |
H17A | 0.28230 | −0.11600 | 0.19710 | 0.0750* | |
H17B | 0.41730 | −0.10540 | 0.33660 | 0.0750* | |
H18A | 0.11260 | 0.03090 | 0.37590 | 0.0940* | |
H18B | 0.09590 | −0.03110 | 0.22120 | 0.0940* | |
H19A | 0.23530 | 0.24150 | 0.30660 | 0.0740* | |
H19B | 0.37330 | 0.25170 | 0.44400 | 0.0740* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0572 (6) | 0.0439 (5) | 0.0533 (5) | 0.0144 (4) | 0.0117 (4) | 0.0177 (4) |
O2 | 0.0841 (8) | 0.0696 (7) | 0.0967 (8) | 0.0459 (6) | 0.0539 (7) | 0.0551 (6) |
N1 | 0.0570 (7) | 0.0382 (5) | 0.0558 (6) | 0.0216 (5) | 0.0276 (5) | 0.0173 (5) |
N2 | 0.0482 (6) | 0.0411 (5) | 0.0550 (6) | 0.0236 (5) | 0.0240 (5) | 0.0224 (5) |
C1 | 0.0463 (6) | 0.0371 (6) | 0.0536 (7) | 0.0211 (5) | 0.0225 (5) | 0.0160 (5) |
C2 | 0.0569 (8) | 0.0476 (7) | 0.0503 (7) | 0.0247 (6) | 0.0234 (6) | 0.0174 (6) |
C3 | 0.0514 (7) | 0.0434 (7) | 0.0511 (7) | 0.0203 (6) | 0.0157 (6) | 0.0082 (5) |
C4 | 0.0447 (7) | 0.0383 (6) | 0.0602 (8) | 0.0189 (5) | 0.0184 (6) | 0.0156 (5) |
C5 | 0.0531 (7) | 0.0445 (7) | 0.0542 (7) | 0.0225 (6) | 0.0237 (6) | 0.0207 (6) |
C6 | 0.0499 (7) | 0.0396 (6) | 0.0486 (7) | 0.0193 (5) | 0.0192 (6) | 0.0120 (5) |
C7 | 0.0678 (10) | 0.0419 (7) | 0.0777 (10) | 0.0143 (7) | 0.0231 (8) | 0.0184 (7) |
C8 | 0.0541 (7) | 0.0432 (7) | 0.0566 (7) | 0.0257 (6) | 0.0280 (6) | 0.0218 (6) |
C9 | 0.0490 (7) | 0.0404 (6) | 0.0527 (7) | 0.0218 (5) | 0.0269 (6) | 0.0188 (5) |
C10 | 0.0473 (7) | 0.0406 (6) | 0.0444 (6) | 0.0186 (5) | 0.0206 (5) | 0.0138 (5) |
C11 | 0.0502 (7) | 0.0410 (6) | 0.0506 (7) | 0.0216 (5) | 0.0256 (6) | 0.0190 (5) |
C12 | 0.0487 (7) | 0.0384 (6) | 0.0585 (8) | 0.0177 (5) | 0.0249 (6) | 0.0183 (5) |
C13 | 0.0436 (7) | 0.0474 (7) | 0.0583 (8) | 0.0180 (6) | 0.0174 (6) | 0.0196 (6) |
C14 | 0.0504 (7) | 0.0511 (7) | 0.0605 (8) | 0.0268 (6) | 0.0246 (6) | 0.0271 (6) |
C15 | 0.0509 (7) | 0.0475 (7) | 0.0601 (8) | 0.0194 (6) | 0.0192 (6) | 0.0240 (6) |
C16 | 0.0567 (8) | 0.0581 (8) | 0.0620 (8) | 0.0354 (7) | 0.0271 (7) | 0.0282 (6) |
C17 | 0.0816 (10) | 0.0525 (8) | 0.0645 (9) | 0.0414 (8) | 0.0325 (8) | 0.0284 (7) |
C18 | 0.0730 (10) | 0.0819 (11) | 0.1191 (15) | 0.0480 (9) | 0.0605 (11) | 0.0659 (11) |
C19 | 0.0761 (10) | 0.0610 (8) | 0.0774 (10) | 0.0451 (8) | 0.0470 (8) | 0.0364 (7) |
O1—C10 | 1.3492 (18) | C16—C17 | 1.501 (2) |
O2—C17 | 1.408 (3) | C18—C19 | 1.500 (3) |
O2—C18 | 1.419 (3) | C2—H2 | 0.9300 |
O1—H1 | 0.8200 | C3—H3 | 0.9300 |
N1—C8 | 1.277 (2) | C5—H5 | 0.9300 |
N1—C1 | 1.4189 (19) | C6—H6 | 0.9300 |
N2—C15 | 1.458 (2) | C7—H7A | 0.9600 |
N2—C16 | 1.461 (2) | C7—H7B | 0.9600 |
N2—C19 | 1.454 (3) | C7—H7C | 0.9600 |
C1—C2 | 1.391 (2) | C8—H8 | 0.9300 |
C1—C6 | 1.3887 (19) | C12—H12 | 0.9300 |
C2—C3 | 1.378 (2) | C13—H13 | 0.9300 |
C3—C4 | 1.391 (2) | C14—H14 | 0.9300 |
C4—C7 | 1.511 (2) | C15—H15A | 0.9700 |
C4—C5 | 1.388 (2) | C15—H15B | 0.9700 |
C5—C6 | 1.383 (2) | C16—H16A | 0.9700 |
C8—C9 | 1.453 (2) | C16—H16B | 0.9700 |
C9—C10 | 1.407 (2) | C17—H17A | 0.9700 |
C9—C14 | 1.395 (2) | C17—H17B | 0.9700 |
C10—C11 | 1.402 (2) | C18—H18A | 0.9700 |
C11—C15 | 1.513 (2) | C18—H18B | 0.9700 |
C11—C12 | 1.383 (2) | C19—H19A | 0.9700 |
C12—C13 | 1.388 (2) | C19—H19B | 0.9700 |
C13—C14 | 1.373 (2) | ||
O1···N1 | 2.6261 (18) | H6···C8 | 2.7300 |
O2···N2 | 2.852 (2) | H6···H8 | 2.3300 |
O1···H15B | 2.5400 | H6···N2ii | 2.9100 |
O1···H19Bi | 2.8300 | H7C···H5 | 2.3500 |
O1···H15A | 2.8200 | H8···C6 | 2.6600 |
O2···H2i | 2.7700 | H8···H6 | 2.3300 |
N1···O1 | 2.6261 (18) | H8···H14 | 2.4300 |
N2···O2 | 2.852 (2) | H12···N2 | 2.5300 |
N1···H1 | 1.9000 | H12···C19 | 2.9800 |
N2···H12 | 2.5300 | H12···H19A | 2.5700 |
N2···H6ii | 2.9100 | H13···H18Bvii | 2.5000 |
C1···C18iii | 3.596 (3) | H14···H8 | 2.4300 |
C8···C12ii | 3.409 (3) | H14···C5vi | 2.8800 |
C10···C14ii | 3.432 (3) | H15A···O1 | 2.8200 |
C12···C8ii | 3.409 (3) | H15A···H16B | 2.2800 |
C12···C19 | 3.368 (2) | H15B···O1 | 2.5400 |
C14···C10ii | 3.432 (3) | H15B···H16A | 2.5900 |
C18···C1iv | 3.596 (3) | H15B···H19B | 2.3000 |
C19···C12 | 3.368 (2) | H16A···H15B | 2.5900 |
C1···H16Bv | 2.8600 | H16A···H19B | 2.4100 |
C1···H18Aiii | 3.0000 | H16B···C1viii | 2.8600 |
C2···H18Aiii | 2.9600 | H16B···C2viii | 3.0300 |
C2···H16Bv | 3.0300 | H16B···H15A | 2.2800 |
C3···H19Aiii | 3.1000 | H17A···H18B | 2.3900 |
C4···H19Aiii | 2.9400 | H17A···H5ii | 2.4600 |
C5···H14vi | 2.8800 | H18A···C1iv | 3.0000 |
C6···H8 | 2.6600 | H18A···C2iv | 2.9600 |
C8···H1 | 2.4200 | H18B···H17A | 2.3900 |
C8···H6 | 2.7300 | H18B···H13vii | 2.5000 |
C11···H19A | 2.8300 | H19A···C3iv | 3.1000 |
C12···H19A | 2.8700 | H19A···C4iv | 2.9400 |
C19···H12 | 2.9800 | H19A···C11 | 2.8300 |
H1···N1 | 1.9000 | H19A···C12 | 2.8700 |
H1···C8 | 2.4200 | H19A···H12 | 2.5700 |
H2···O2i | 2.7700 | H19B···H15B | 2.3000 |
H5···H7C | 2.3500 | H19B···H16A | 2.4100 |
H5···H17Aii | 2.4600 | H19B···O1i | 2.8300 |
C17—O2—C18 | 110.04 (14) | C5—C6—H6 | 120.00 |
C10—O1—H1 | 109.00 | C4—C7—H7A | 109.00 |
C1—N1—C8 | 120.07 (13) | C4—C7—H7B | 109.00 |
C15—N2—C19 | 111.36 (13) | C4—C7—H7C | 109.00 |
C16—N2—C19 | 108.24 (13) | H7A—C7—H7B | 110.00 |
C15—N2—C16 | 111.27 (14) | H7A—C7—H7C | 109.00 |
N1—C1—C6 | 122.95 (12) | H7B—C7—H7C | 109.00 |
C2—C1—C6 | 118.83 (13) | N1—C8—H8 | 119.00 |
N1—C1—C2 | 118.13 (12) | C9—C8—H8 | 119.00 |
C1—C2—C3 | 120.53 (13) | C11—C12—H12 | 119.00 |
C2—C3—C4 | 121.30 (13) | C13—C12—H12 | 119.00 |
C3—C4—C5 | 117.56 (14) | C12—C13—H13 | 120.00 |
C5—C4—C7 | 120.84 (14) | C14—C13—H13 | 120.00 |
C3—C4—C7 | 121.57 (13) | C9—C14—H14 | 120.00 |
C4—C5—C6 | 121.83 (13) | C13—C14—H14 | 120.00 |
C1—C6—C5 | 119.93 (13) | N2—C15—H15A | 109.00 |
N1—C8—C9 | 122.64 (14) | N2—C15—H15B | 109.00 |
C8—C9—C10 | 121.32 (13) | C11—C15—H15A | 109.00 |
C8—C9—C14 | 119.69 (13) | C11—C15—H15B | 109.00 |
C10—C9—C14 | 118.95 (13) | H15A—C15—H15B | 108.00 |
O1—C10—C11 | 117.69 (13) | N2—C16—H16A | 110.00 |
C9—C10—C11 | 120.53 (13) | N2—C16—H16B | 110.00 |
O1—C10—C9 | 121.76 (13) | C17—C16—H16A | 110.00 |
C10—C11—C12 | 118.40 (13) | C17—C16—H16B | 110.00 |
C12—C11—C15 | 123.20 (13) | H16A—C16—H16B | 108.00 |
C10—C11—C15 | 118.29 (13) | O2—C17—H17A | 109.00 |
C11—C12—C13 | 121.68 (14) | O2—C17—H17B | 109.00 |
C12—C13—C14 | 119.68 (15) | C16—C17—H17A | 109.00 |
C9—C14—C13 | 120.76 (14) | C16—C17—H17B | 109.00 |
N2—C15—C11 | 113.61 (14) | H17A—C17—H17B | 108.00 |
N2—C16—C17 | 110.36 (15) | O2—C18—H18A | 109.00 |
O2—C17—C16 | 112.22 (15) | O2—C18—H18B | 109.00 |
O2—C18—C19 | 112.08 (17) | C19—C18—H18A | 109.00 |
N2—C19—C18 | 110.12 (15) | C19—C18—H18B | 109.00 |
C1—C2—H2 | 120.00 | H18A—C18—H18B | 108.00 |
C3—C2—H2 | 120.00 | N2—C19—H19A | 110.00 |
C2—C3—H3 | 119.00 | N2—C19—H19B | 110.00 |
C4—C3—H3 | 119.00 | C18—C19—H19A | 110.00 |
C4—C5—H5 | 119.00 | C18—C19—H19B | 110.00 |
C6—C5—H5 | 119.00 | H19A—C19—H19B | 108.00 |
C1—C6—H6 | 120.00 | ||
C17—O2—C18—C19 | −56.61 (19) | N1—C8—C9—C10 | −3.8 (3) |
C18—O2—C17—C16 | 56.19 (18) | N1—C8—C9—C14 | 178.64 (17) |
C8—N1—C1—C6 | −39.4 (3) | C10—C9—C14—C13 | 0.8 (3) |
C8—N1—C1—C2 | 143.89 (18) | C14—C9—C10—C11 | −0.2 (2) |
C1—N1—C8—C9 | 176.53 (15) | C8—C9—C10—O1 | 0.5 (2) |
C19—N2—C15—C11 | −79.79 (16) | C14—C9—C10—O1 | 178.05 (15) |
C15—N2—C16—C17 | −180.00 (13) | C8—C9—C14—C13 | 178.35 (16) |
C16—N2—C15—C11 | 159.35 (13) | C8—C9—C10—C11 | −177.71 (15) |
C15—N2—C19—C18 | 179.71 (14) | C9—C10—C11—C12 | −0.6 (2) |
C19—N2—C16—C17 | 57.33 (16) | O1—C10—C11—C15 | −2.6 (2) |
C16—N2—C19—C18 | −57.68 (17) | O1—C10—C11—C12 | −178.89 (15) |
N1—C1—C6—C5 | −177.41 (17) | C9—C10—C11—C15 | 175.65 (15) |
N1—C1—C2—C3 | 178.14 (17) | C12—C11—C15—N2 | −14.1 (2) |
C2—C1—C6—C5 | −0.7 (3) | C10—C11—C15—N2 | 169.80 (14) |
C6—C1—C2—C3 | 1.3 (3) | C15—C11—C12—C13 | −175.25 (16) |
C1—C2—C3—C4 | −1.2 (3) | C10—C11—C12—C13 | 0.8 (3) |
C2—C3—C4—C5 | 0.6 (3) | C11—C12—C13—C14 | −0.2 (3) |
C2—C3—C4—C7 | −177.38 (18) | C12—C13—C14—C9 | −0.6 (3) |
C3—C4—C5—C6 | 0.0 (3) | N2—C16—C17—O2 | −57.79 (17) |
C7—C4—C5—C6 | 177.97 (18) | O2—C18—C19—N2 | 58.52 (19) |
C4—C5—C6—C1 | 0.1 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x+1, y+1, z; (iv) x−1, y−1, z; (v) x, y+1, z; (vi) −x+1, −y+2, −z; (vii) −x, −y, −z; (viii) x, y−1, z. |
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.90 | 2.6261 (18) | 147 |
C12—H12···N2 | 0.93 | 2.53 | 2.876 (2) | 102 |
C19—H19A···Cg2iv | 0.97 | 2.96 | 3.732 (3) | 137 |
Symmetry code: (iv) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C19H22N2O2 |
Mr | 310.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.807 (3), 10.091 (3), 10.528 (3) |
α, β, γ (°) | 99.78 (2), 109.34 (2), 115.18 (2) |
V (Å3) | 828.7 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.53 × 0.40 × 0.23 |
Data collection | |
Diffractometer | Stoe IPDS 2 |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.958, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15421, 3443, 2894 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.121, 1.08 |
No. of reflections | 3443 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.90 | 2.6261 (18) | 147 |
C19—H19A···Cg2i | 0.97 | 2.96 | 3.732 (3) | 137 |
Symmetry code: (i) x−1, y−1, z. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). AJ, HS, SATB and MA thank the Shiraz University Research Council for financial support (grant No. 89-GR—SC-23).
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Schiff bases, named for Hugo Schiff with the azomethine or imine group (—C═ N—) usually synthesized by condensation of a primary amine and an active carbonyl group under specific conditions. These compounds show a broad range of applications such as corrosion inhibitors (Emregül et al., 2006), catalysts (Sessler et al., 2006), pigments and polymer stabilizers. Schiff bases possess high biological activities including antibacterial (Jarrahpour et al., 2006), antifungal (Singh et al., 2006), antitumor (Mladenova et al., 2002), antimalarial (Przybylski et al., 2009), antiviral (Jarrahpour et al., 2007) and antipyretic properties (Dhar et al., 1982). Schiff bases are also good intermediates for the synthesis of other chemical substances such as 2-azetidinones.
As shown in Fig. 1, the morpholine ring (N2/O2/C16–C19) of the title compound (I) adopts a chair conformation with puckering parameters QT, θ and φ of 0.5642 (18) Å, 177.32 (17) ° and φ = 10 (4) ° (Cremer & Pople (1975). The dihedral angle between the (C1–C6) and (C9–C14) benzene rings in (I) is 42.67 (8)°. The bond lengths exhibit normal values (Allen et al. 1987) and are comparable with those in our similar structure previously published (Akkurt et al., 2008).
The molecular conformation of (I) is stabilized by intramolecular weak C12—H12···N2 and strong O1—H1···N1 hydrogen bonds (Table 1). In the crystal structure, a C—H···π interaction (Table 1) and a π-π stacking interaction between the C9–C14 benzene rings contribute to the stabilization of the crystal packing [Cg3···Cg3ii(symmetry code ii = 1 - x, 1 - y, -z) = 3.6155 (15) Å, where Cg3 is a centroid of the C9–C14 benzene ring]. Fig. 2 shows the crystal packing of (I) down the a axis.