organic compounds
(E)-4-Hydroxy-6-methyl-3-[1-(2-phenylhydrazinylidene)ethyl]-2H-pyran-2-one
aLaboratoire de Matériaux Moléculaires et Complexes, Faculté de Technologie Université Ferhat Abbes de Setif, Sétif, Algérie 19000, Algeria, bLaboratoire de Physicochimie Analytique et Cristallochimie de Matériaux Organométalliques et Biomoléculaires, Département de Chimie, Faculté des Sciences Exactes, Université des Fréres Mentouri, 2500 Constantine 1, Algeria, cEcole Normale Supérieure de Constantine, Ville Universitaire Ali Mendjeli, Constantine, Algeria, dLaboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000, Oujda, Morocco, eFaculté Pluridisciplinaire Nador BP 300, Selouane, 62702, Nador, Morocco, fInstitut Jean Lamour UMR, 7198, Parc de Saurupt, CS 14234 F 54042 Nancy, France, and gDépartement de Chimie, Faculté des Sciences Université, Ferhat Abbes de Sétif, Sétif Algérie 19000, Algeria
*Correspondence e-mail: djedouani_amel@yahoo.fr
The title compound, C14H14N2O3, crystallized with three crystallographically independent molecules (A, B and C) in the The three molecules each have an E conformation about the C=N bond but differ in the orientation of the phenyl and pyran rings. The dihedral angles between the phenyl and pyran ring planes are 14.30 (1), 28.38 (1) and 25.58 (1)° in molecules A, B and C, respectively. There is an intramolecular O—H⋯N hydrogen bond in each molecule with an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming layers parallel to (001), enclosing R22(8) and R33(21) ring motifs. The layers are linked via C—H⋯π interactions, forming bilayers, which are joined by a further C—H⋯π interaction, forming a three-dimensional structure.
Keywords: crystal structure; phenylhydrazone ligand; pyran-2-one; hydrogen bonding.
CCDC reference: 1477449
Structure description
et al., 2010). The principle aim of investigating the structural chemistry of is to study their coordination properties (Garcia-Herbosa et al. 1994). In the present paper, we describe the synthesis and of a new hydrazone ligand.
have received much attention recently due to their biological activities (AjaniThe title compound, Fig. 1, crystallized with three independent molecules (A, B and C) in the The three molecules exist in a trans or E conformation with respect to the C=N bond but differ in the orientation of the phenyl ring with respect the pyran-2-one ring. The dihedral angles between the phenyl and pyran ring planes are 14.30 (1), 28.38 (1) and 25.58 (1)°, in molecules A, B and C, respectively. The N—N distances [1.356 (2)-1.377 (2) Å] are rather long compared to those observed in related compounds, viz. ethyl 4-chloro-3-oxo-2-(phenylhydrazono)butyrate [1.300 (2) Å; Alpaslan et al., 2005a], (E)-ethyl 4-chloro-3-[2-(2-fluorophenyl)hydrazono]butanoate [1.306 (2) Å; Alpaslan et al., 2005b] and (Z)-ethyl 4-chloro-2-[2-(2-methoxyphenyl) hydrazono]-3-oxobutanoate [1.300 (2) Å; Alpaslan et al., 2005c]. This elongation may be the result of the intramolecular O—H⋯N hydrogen bonds that occur in each molecule (Fig. 1 and Table 1), and which form an S(6) ring motif. The C—Niminium bond lengths [1.294 (2)–1.301 (2) Å] are comparable to that observed in 1-dimethylamino-3-dimethyliminio-2-(p-methoxyphenyl) prop-1-ene perchlorate [1.307 (3) Å; Girija et al., 2004].
In the crystal, the three molecules are linked via N—H⋯O and C—H⋯O hydrogen bonds forming layers parallel to the ab plane (Table 1 and Fig. 2). The layers are linked via C—H⋯π interactions forming bilayers, which in turn are joined by a further C—H⋯π interaction, forming a three-dimensional structure (Table 1 and Fig. 3).
Synthesis and crystallization
The title compound was prepared by reacting equimolar amounts of dehydroacetic acid and phenylhydrazine (1:1 M ratio), in absolute ethanol. The mixture was refluxed for 1 h, then the yellow solid which precipitated was filtered and recrystallized from 75% ethanol and 25% distilled water, giving colourless prismatic crystals.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1477449
10.1107/S241431461600729X/sj4030sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S241431461600729X/sj4030Isup2.hkl
Supporting information file. DOI: 10.1107/S241431461600729X/sj4030Isup3.cml
The title compound was prepared by reacting equimolar amounts of dehydroacetic acid and phenylhydrazine (1:1 M ratio), in absolute ethanol. The mixture was refluxed for 1 h, then the yellow solid which precipitated was filtered and recrystallized from 75% ethanol and 25% distilled water, giving colourless prismatic crystals.
The title compound was prepared by reacting equimolar amounts of dehydroacetic acid and phenylhydrazine (1:1 M ratio), in absolute ethanol. The mixture was refluxed for 1 h, then the yellow solid which precipitated was filtered and recrystallized from 75% ethanol and 25% distilled water, giving colourless prismatic crystals.
Hydrazones have received much attention recently due to their biological activities (Ajani et al., 2010). The principle aim of investigating the structural chemistry of
is to study their coordination properties (Garcia-Herbosa et al. 1994). In the present paper, we describe the synthesis and of a new hydrazone ligand.The title compound, Fig, 1, crystallized with three independent molecules (A, B and C) in the ═N bond but differ in the orientation of the phenyl ring with respect the pyran-2-one ring. The dihedral angles between the phenyl and pyran ring planes are 14.30 (1), 28.38 (1) and 25.58 (1)°, in molecules A, B and C, respectively. The N—N distances [1.356 (2)-1.377 (2) Å] are rather long compared to those observed in related compounds, viz. ethyl 4-chloro-3-oxo-2-(phenylhydrazono)butyrate [1.300 (2) Å; Alpaslan et al., 2005a], (E)-ethyl 4-chloro-3-[2-(2-fluorophenyl)hydrazono]butanoate [1.306 (2) Å; Alpaslan et al., 2005b] and (Z)-ethyl 4-chloro-2-[2-(2-methoxyphenyl) hydrazono]-3-oxobutanoate [1.300 (2) Å; Alpaslan et al., 2005c]. This elongation may be the result of the intramolecular O—H···N hydrogen bonds that occur in each molecule (Fig. 1 and Table 1), and which form an S(6) ring motif. The C—Niminium bond lengths [1.294 (2)–1.301 (2) Å] are comparable to that observed in 1-dimethylamino-3-dimethyliminio-2-(p-methoxyphenyl) prop-1-ene perchlorate [1.307 (3) Å; Girija et al., 2004].
The three molecules exist in a trans or E conformation with respect to the CIn the crystal, the three molecules are linked via N—H···O and C—H···O hydrogen bonds forming layers parallel to the ab plane (Table 2 and Fig. 2). The layers are linked via C—H···π interactions forming bilayers, which in turn are joined by a further C—H···π interaction, forming a three-dimensional structure (Table 2 and Fig. 3).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the three independent molecules (A, B and C) of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A view along the c axis of the hydrogen-bonded (dashed lines; see Table 1) layer in the crystal of the title compound (molecule A blue, molecule B red, molecule C green). | |
Fig. 3. A view along the b axis of the crystal packing of the title compound. The hydrogen bonds and C—H···π interactions are shown as dashed lines (see Table 1). H atoms are shown as grey balls and those H atoms not involved in these interactions have been omitted for clarity. |
C14H14N2O3 | F(000) = 3264 |
Mr = 258.27 | Dx = 1.410 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 30.1064 (12) Å | Cell parameters from 13642 reflections |
b = 17.5911 (7) Å | θ = 3.0–28.5° |
c = 13.7937 (8) Å | µ = 0.10 mm−1 |
β = 92.613 (4)° | T = 293 K |
V = 7297.6 (6) Å3 | Prism, colourless |
Z = 24 | 0.1 × 0.1 × 0.1 mm |
Agilent Xcalibur Sapphire 1 (long nozzle) diffractometer | 7444 independent reflections |
Radiation source: fine-focus sealed tube | 4849 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 8.2632 pixels mm-1 | θmax = 26.4°, θmin = 3.0° |
ω scans | h = −37→37 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −21→21 |
Tmin = 0.725, Tmax = 1.000 | l = −17→17 |
37468 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0563P)2 + 1.4052P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.125 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.29 e Å−3 |
7444 reflections | Δρmin = −0.21 e Å−3 |
524 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2014), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00019 (4) |
C14H14N2O3 | V = 7297.6 (6) Å3 |
Mr = 258.27 | Z = 24 |
Monoclinic, C2/c | Mo Kα radiation |
a = 30.1064 (12) Å | µ = 0.10 mm−1 |
b = 17.5911 (7) Å | T = 293 K |
c = 13.7937 (8) Å | 0.1 × 0.1 × 0.1 mm |
β = 92.613 (4)° |
Agilent Xcalibur Sapphire 1 (long nozzle) diffractometer | 7444 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 4849 reflections with I > 2σ(I) |
Tmin = 0.725, Tmax = 1.000 | Rint = 0.058 |
37468 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.29 e Å−3 |
7444 reflections | Δρmin = −0.21 e Å−3 |
524 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.92018 (4) | 0.11844 (8) | 0.83644 (11) | 0.0362 (4) | |
O2A | 0.96328 (5) | 0.01943 (8) | 0.82982 (13) | 0.0463 (4) | |
O3A | 0.80749 (4) | −0.00288 (8) | 0.85760 (12) | 0.0404 (4) | |
H3A | 0.8117 | −0.0489 | 0.8558 | 0.061* | |
N1A | 0.85018 (5) | −0.12222 (9) | 0.84702 (11) | 0.0272 (4) | |
N2A | 0.84735 (5) | −0.19903 (9) | 0.84125 (13) | 0.0335 (4) | |
H2A | 0.8705 | −0.2298 | 0.8283 | 0.050* | |
C1A | 0.92495 (6) | 0.04004 (12) | 0.83610 (15) | 0.0306 (5) | |
C2A | 0.88587 (6) | −0.00496 (11) | 0.84325 (13) | 0.0244 (4) | |
C3A | 0.84554 (6) | 0.03292 (11) | 0.85052 (15) | 0.0284 (4) | |
C4A | 0.84330 (7) | 0.11340 (12) | 0.84907 (15) | 0.0335 (5) | |
H4A | 0.8160 | 0.1378 | 0.8528 | 0.040* | |
C5A | 0.88017 (7) | 0.15357 (12) | 0.84241 (15) | 0.0328 (5) | |
C6A | 0.88806 (6) | −0.08819 (11) | 0.84065 (13) | 0.0254 (4) | |
C7A | 0.80575 (6) | −0.23277 (11) | 0.84855 (15) | 0.0303 (5) | |
C8A | 0.80153 (7) | −0.30963 (12) | 0.82736 (16) | 0.0346 (5) | |
H8A | 0.8261 | −0.3375 | 0.8096 | 0.042* | |
C9A | 0.76071 (7) | −0.34457 (13) | 0.83280 (17) | 0.0415 (6) | |
H9A | 0.7581 | −0.3962 | 0.8190 | 0.050* | |
C10A | 0.72387 (8) | −0.30471 (14) | 0.85816 (19) | 0.0490 (6) | |
H10A | 0.6964 | −0.3287 | 0.8612 | 0.059* | |
C11A | 0.72826 (8) | −0.22918 (15) | 0.8789 (2) | 0.0592 (8) | |
H11A | 0.7034 | −0.2016 | 0.8960 | 0.071* | |
C12A | 0.76869 (7) | −0.19293 (13) | 0.87504 (19) | 0.0492 (7) | |
H12A | 0.7710 | −0.1415 | 0.8903 | 0.059* | |
C51A | 0.88479 (8) | 0.23714 (12) | 0.84069 (18) | 0.0468 (6) | |
H51A | 0.8558 | 0.2601 | 0.8393 | 0.070* | |
H51B | 0.8999 | 0.2520 | 0.7840 | 0.070* | |
H51C | 0.9016 | 0.2536 | 0.8977 | 0.070* | |
C61A | 0.93004 (6) | −0.13205 (12) | 0.82913 (17) | 0.0383 (5) | |
H61A | 0.9371 | −0.1603 | 0.8873 | 0.057* | |
H61B | 0.9539 | −0.0975 | 0.8172 | 0.057* | |
H61C | 0.9261 | −0.1665 | 0.7754 | 0.057* | |
O1B | 0.82066 (4) | 0.19617 (7) | 1.10144 (11) | 0.0335 (3) | |
O2B | 0.89226 (5) | 0.21154 (8) | 1.08964 (12) | 0.0435 (4) | |
O3B | 0.82796 (4) | −0.03206 (8) | 1.11672 (12) | 0.0388 (4) | |
H3B | 0.8535 | −0.0477 | 1.1134 | 0.058* | |
N1B | 0.90859 (5) | −0.02693 (9) | 1.10124 (12) | 0.0265 (4) | |
N2B | 0.94645 (5) | −0.07052 (9) | 1.09691 (12) | 0.0306 (4) | |
H2B | 0.9707 | −0.0538 | 1.1291 | 0.046* | |
C1B | 0.86300 (6) | 0.16466 (11) | 1.09636 (15) | 0.0280 (5) | |
C2B | 0.86675 (6) | 0.08392 (10) | 1.09932 (13) | 0.0241 (4) | |
C3B | 0.82784 (6) | 0.04126 (11) | 1.11247 (14) | 0.0273 (4) | |
C4B | 0.78639 (6) | 0.07876 (12) | 1.12250 (15) | 0.0330 (5) | |
H4B | 0.7610 | 0.0505 | 1.1337 | 0.040* | |
C5B | 0.78377 (6) | 0.15347 (12) | 1.11605 (15) | 0.0307 (5) | |
C6B | 0.90956 (6) | 0.04645 (11) | 1.09164 (13) | 0.0246 (4) | |
C7B | 0.94002 (6) | −0.14901 (11) | 1.09955 (14) | 0.0263 (4) | |
C8B | 0.97515 (7) | −0.19505 (12) | 1.13130 (16) | 0.0351 (5) | |
H8B | 1.0020 | −0.1734 | 1.1527 | 0.042* | |
C9B | 0.97026 (7) | −0.27271 (12) | 1.13106 (17) | 0.0408 (6) | |
H9B | 0.9939 | −0.3033 | 1.1526 | 0.049* | |
C10B | 0.93070 (7) | −0.30586 (12) | 1.09932 (17) | 0.0401 (6) | |
H10B | 0.9275 | −0.3584 | 1.0997 | 0.048* | |
C11B | 0.89621 (7) | −0.26032 (12) | 1.06725 (16) | 0.0366 (5) | |
H11B | 0.8696 | −0.2824 | 1.0451 | 0.044* | |
C12B | 0.90023 (6) | −0.18240 (11) | 1.06722 (15) | 0.0316 (5) | |
H12B | 0.8764 | −0.1522 | 1.0457 | 0.038* | |
C51B | 0.74299 (7) | 0.20061 (13) | 1.12286 (18) | 0.0430 (6) | |
H51D | 0.7191 | 0.1695 | 1.1440 | 0.064* | |
H51E | 0.7350 | 0.2218 | 1.0603 | 0.064* | |
H51F | 0.7486 | 0.2410 | 1.1686 | 0.064* | |
C61B | 0.95219 (6) | 0.08598 (12) | 1.07389 (17) | 0.0367 (5) | |
H61D | 0.9677 | 0.0964 | 1.1348 | 0.055* | |
H61E | 0.9461 | 0.1329 | 1.0402 | 0.055* | |
H61F | 0.9703 | 0.0541 | 1.0352 | 0.055* | |
O1C | 1.10738 (4) | 0.43283 (7) | 1.19270 (10) | 0.0281 (3) | |
O2C | 1.07871 (4) | 0.31901 (8) | 1.18408 (11) | 0.0386 (4) | |
O3C | 0.99149 (4) | 0.53864 (7) | 1.12150 (12) | 0.0360 (4) | |
H3C | 0.9710 | 0.5086 | 1.1105 | 0.054* | |
N1C | 0.95353 (5) | 0.41541 (9) | 1.10040 (11) | 0.0250 (4) | |
N2C | 0.91419 (5) | 0.37916 (9) | 1.07685 (12) | 0.0275 (4) | |
H2C | 0.9105 | 0.3322 | 1.0977 | 0.041* | |
C1C | 1.07080 (6) | 0.38597 (11) | 1.17251 (14) | 0.0253 (4) | |
C2C | 1.02955 (6) | 0.42148 (10) | 1.14246 (13) | 0.0230 (4) | |
C3C | 1.02809 (6) | 0.50082 (11) | 1.14407 (14) | 0.0253 (4) | |
C4C | 1.06635 (6) | 0.54419 (11) | 1.16983 (15) | 0.0304 (5) | |
H4C | 1.0646 | 0.5969 | 1.1715 | 0.036* | |
C5C | 1.10493 (6) | 0.50989 (11) | 1.19177 (14) | 0.0270 (4) | |
C6C | 0.98991 (6) | 0.37651 (10) | 1.11594 (13) | 0.0232 (4) | |
C7C | 0.87613 (6) | 0.42396 (11) | 1.06602 (14) | 0.0245 (4) | |
C8C | 0.83493 (6) | 0.39141 (12) | 1.08257 (15) | 0.0320 (5) | |
H8C | 0.8333 | 0.3411 | 1.1028 | 0.038* | |
C9C | 0.79655 (6) | 0.43373 (12) | 1.06902 (16) | 0.0358 (5) | |
H9C | 0.7693 | 0.4118 | 1.0811 | 0.043* | |
C10C | 0.79808 (7) | 0.50790 (12) | 1.03792 (15) | 0.0351 (5) | |
H10C | 0.7721 | 0.5359 | 1.0280 | 0.042* | |
C11C | 0.83893 (7) | 0.54007 (12) | 1.02172 (15) | 0.0324 (5) | |
H11C | 0.8403 | 0.5903 | 1.0010 | 0.039* | |
C12C | 0.87773 (6) | 0.49917 (11) | 1.03562 (14) | 0.0272 (4) | |
H12C | 0.9049 | 0.5219 | 1.0247 | 0.033* | |
C51C | 1.14880 (6) | 0.54544 (12) | 1.21459 (16) | 0.0354 (5) | |
H51G | 1.1679 | 0.5373 | 1.1616 | 0.053* | |
H51H | 1.1620 | 0.5230 | 1.2725 | 0.053* | |
H51I | 1.1450 | 0.5990 | 1.2244 | 0.053* | |
C61C | 0.98990 (7) | 0.29251 (11) | 1.10723 (18) | 0.0379 (5) | |
H61G | 0.9784 | 0.2705 | 1.1646 | 0.057* | |
H61H | 1.0197 | 0.2749 | 1.0998 | 0.057* | |
H61I | 0.9716 | 0.2777 | 1.0516 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0283 (7) | 0.0266 (8) | 0.0535 (10) | −0.0037 (6) | −0.0020 (7) | 0.0060 (7) |
O2A | 0.0202 (7) | 0.0350 (9) | 0.0836 (13) | −0.0030 (7) | 0.0003 (7) | 0.0046 (8) |
O3A | 0.0231 (7) | 0.0312 (8) | 0.0674 (11) | −0.0024 (6) | 0.0066 (7) | 0.0023 (8) |
N1A | 0.0252 (8) | 0.0251 (9) | 0.0311 (10) | −0.0036 (7) | −0.0018 (7) | 0.0001 (7) |
N2A | 0.0251 (9) | 0.0242 (9) | 0.0511 (12) | −0.0035 (7) | −0.0001 (8) | −0.0045 (8) |
C1A | 0.0261 (10) | 0.0288 (11) | 0.0365 (12) | −0.0021 (9) | −0.0030 (9) | 0.0044 (9) |
C2A | 0.0226 (9) | 0.0260 (10) | 0.0243 (10) | −0.0031 (8) | −0.0011 (8) | 0.0010 (8) |
C3A | 0.0230 (10) | 0.0307 (11) | 0.0315 (12) | −0.0026 (9) | 0.0000 (8) | 0.0020 (9) |
C4A | 0.0288 (11) | 0.0305 (11) | 0.0413 (13) | 0.0043 (9) | 0.0036 (9) | 0.0031 (10) |
C5A | 0.0344 (11) | 0.0286 (11) | 0.0354 (12) | 0.0024 (9) | −0.0003 (9) | 0.0042 (9) |
C6A | 0.0234 (9) | 0.0287 (11) | 0.0239 (10) | −0.0019 (8) | −0.0020 (8) | −0.0012 (8) |
C7A | 0.0284 (10) | 0.0290 (11) | 0.0335 (12) | −0.0052 (9) | 0.0006 (9) | 0.0002 (9) |
C8A | 0.0313 (11) | 0.0265 (11) | 0.0455 (14) | 0.0012 (9) | −0.0039 (9) | 0.0030 (10) |
C9A | 0.0443 (13) | 0.0261 (11) | 0.0536 (15) | −0.0092 (10) | −0.0031 (11) | 0.0038 (11) |
C10A | 0.0395 (13) | 0.0414 (14) | 0.0671 (18) | −0.0181 (11) | 0.0125 (12) | −0.0008 (12) |
C11A | 0.0386 (13) | 0.0454 (15) | 0.096 (2) | −0.0115 (12) | 0.0291 (14) | −0.0160 (15) |
C12A | 0.0416 (13) | 0.0324 (13) | 0.0755 (19) | −0.0122 (10) | 0.0235 (12) | −0.0170 (12) |
C51A | 0.0501 (14) | 0.0290 (12) | 0.0616 (17) | 0.0000 (11) | 0.0062 (12) | 0.0069 (12) |
C61A | 0.0279 (11) | 0.0291 (12) | 0.0579 (15) | −0.0019 (9) | 0.0020 (10) | −0.0034 (10) |
O1B | 0.0268 (7) | 0.0237 (7) | 0.0497 (10) | 0.0018 (6) | −0.0016 (6) | −0.0010 (7) |
O2B | 0.0315 (8) | 0.0209 (8) | 0.0785 (12) | −0.0044 (7) | 0.0052 (8) | −0.0001 (8) |
O3B | 0.0274 (7) | 0.0222 (8) | 0.0666 (11) | −0.0028 (6) | 0.0006 (7) | 0.0018 (7) |
N1B | 0.0257 (8) | 0.0221 (9) | 0.0315 (10) | 0.0030 (7) | 0.0003 (7) | −0.0012 (7) |
N2B | 0.0240 (8) | 0.0231 (9) | 0.0445 (11) | 0.0003 (7) | −0.0003 (7) | −0.0015 (8) |
C1B | 0.0241 (10) | 0.0247 (10) | 0.0351 (12) | 0.0008 (9) | −0.0009 (8) | −0.0010 (9) |
C2B | 0.0255 (9) | 0.0220 (10) | 0.0244 (10) | −0.0014 (8) | −0.0027 (8) | −0.0012 (8) |
C3B | 0.0264 (10) | 0.0230 (10) | 0.0319 (12) | −0.0048 (8) | −0.0053 (8) | −0.0012 (9) |
C4B | 0.0232 (10) | 0.0306 (12) | 0.0449 (13) | −0.0048 (9) | −0.0026 (9) | −0.0002 (10) |
C5B | 0.0238 (10) | 0.0328 (12) | 0.0351 (12) | −0.0010 (9) | −0.0030 (8) | −0.0028 (9) |
C6B | 0.0270 (10) | 0.0232 (10) | 0.0233 (10) | −0.0017 (8) | −0.0019 (8) | −0.0006 (8) |
C7B | 0.0286 (10) | 0.0211 (10) | 0.0293 (11) | 0.0002 (8) | 0.0035 (8) | −0.0016 (8) |
C8B | 0.0253 (10) | 0.0292 (11) | 0.0504 (14) | 0.0001 (9) | −0.0021 (9) | −0.0034 (10) |
C9B | 0.0356 (12) | 0.0261 (11) | 0.0602 (16) | 0.0096 (10) | −0.0031 (11) | −0.0015 (11) |
C10B | 0.0410 (13) | 0.0215 (11) | 0.0578 (16) | −0.0008 (10) | 0.0028 (11) | −0.0039 (10) |
C11B | 0.0318 (11) | 0.0290 (11) | 0.0488 (14) | −0.0056 (9) | −0.0012 (10) | −0.0046 (10) |
C12B | 0.0270 (10) | 0.0282 (11) | 0.0391 (13) | 0.0030 (9) | −0.0026 (9) | −0.0018 (9) |
C51B | 0.0309 (11) | 0.0402 (14) | 0.0573 (16) | 0.0049 (10) | −0.0037 (10) | −0.0030 (11) |
C61B | 0.0278 (11) | 0.0282 (11) | 0.0546 (15) | −0.0013 (9) | 0.0060 (10) | −0.0007 (10) |
O1C | 0.0209 (6) | 0.0242 (7) | 0.0389 (8) | −0.0009 (6) | −0.0027 (6) | 0.0024 (6) |
O2C | 0.0285 (8) | 0.0227 (8) | 0.0638 (11) | 0.0028 (6) | −0.0082 (7) | 0.0031 (7) |
O3C | 0.0238 (7) | 0.0225 (7) | 0.0613 (11) | 0.0027 (6) | −0.0035 (7) | 0.0011 (7) |
N1C | 0.0187 (8) | 0.0240 (9) | 0.0322 (9) | −0.0014 (7) | −0.0013 (7) | −0.0010 (7) |
N2C | 0.0195 (8) | 0.0198 (8) | 0.0428 (11) | −0.0017 (6) | −0.0043 (7) | 0.0020 (7) |
C1C | 0.0235 (9) | 0.0231 (10) | 0.0292 (11) | −0.0026 (8) | 0.0012 (8) | −0.0006 (8) |
C2C | 0.0204 (9) | 0.0234 (10) | 0.0254 (10) | −0.0008 (8) | 0.0031 (7) | −0.0001 (8) |
C3C | 0.0223 (10) | 0.0222 (10) | 0.0314 (11) | 0.0024 (8) | 0.0016 (8) | 0.0017 (8) |
C4C | 0.0290 (11) | 0.0211 (10) | 0.0412 (13) | −0.0032 (8) | 0.0020 (9) | −0.0015 (9) |
C5C | 0.0290 (10) | 0.0234 (10) | 0.0286 (11) | −0.0040 (8) | 0.0024 (8) | −0.0004 (9) |
C6C | 0.0225 (9) | 0.0222 (10) | 0.0251 (10) | −0.0010 (8) | 0.0016 (8) | −0.0001 (8) |
C7C | 0.0213 (9) | 0.0236 (10) | 0.0282 (11) | 0.0010 (8) | −0.0033 (8) | −0.0042 (8) |
C8C | 0.0262 (10) | 0.0278 (11) | 0.0415 (13) | −0.0039 (9) | −0.0018 (9) | −0.0008 (9) |
C9C | 0.0217 (10) | 0.0383 (13) | 0.0470 (14) | −0.0044 (9) | −0.0026 (9) | −0.0048 (10) |
C10C | 0.0259 (10) | 0.0370 (12) | 0.0414 (13) | 0.0090 (9) | −0.0083 (9) | −0.0072 (10) |
C11C | 0.0350 (11) | 0.0257 (11) | 0.0359 (12) | 0.0053 (9) | −0.0065 (9) | −0.0012 (9) |
C12C | 0.0246 (10) | 0.0245 (10) | 0.0323 (11) | −0.0026 (8) | −0.0024 (8) | −0.0012 (9) |
C51C | 0.0286 (11) | 0.0349 (12) | 0.0421 (13) | −0.0081 (9) | −0.0042 (9) | 0.0015 (10) |
C61C | 0.0264 (11) | 0.0239 (11) | 0.0630 (16) | 0.0001 (9) | −0.0030 (10) | −0.0057 (10) |
O1A—C5A | 1.360 (2) | C7B—C8B | 1.387 (3) |
O1A—C1A | 1.387 (2) | C7B—C12B | 1.389 (3) |
O2A—C1A | 1.216 (2) | C8B—C9B | 1.374 (3) |
O3A—C3A | 1.315 (2) | C8B—H8B | 0.9300 |
O3A—H3A | 0.8200 | C9B—C10B | 1.379 (3) |
N1A—C6A | 1.294 (2) | C9B—H9B | 0.9300 |
N1A—N2A | 1.356 (2) | C10B—C11B | 1.369 (3) |
N2A—C7A | 1.394 (2) | C10B—H10B | 0.9300 |
N2A—H2A | 0.9064 | C11B—C12B | 1.376 (3) |
C1A—C2A | 1.425 (3) | C11B—H11B | 0.9300 |
C2A—C3A | 1.393 (3) | C12B—H12B | 0.9300 |
C2A—C6A | 1.466 (3) | C51B—H51D | 0.9600 |
C3A—C4A | 1.417 (3) | C51B—H51E | 0.9600 |
C4A—C5A | 1.323 (3) | C51B—H51F | 0.9600 |
C4A—H4A | 0.9300 | C61B—H61D | 0.9600 |
C5A—C51A | 1.477 (3) | C61B—H61E | 0.9600 |
C6A—C61A | 1.495 (3) | C61B—H61F | 0.9600 |
C7A—C12A | 1.381 (3) | O1C—C5C | 1.358 (2) |
C7A—C8A | 1.388 (3) | O1C—C1C | 1.393 (2) |
C8A—C9A | 1.379 (3) | O2C—C1C | 1.211 (2) |
C8A—H8A | 0.9300 | O3C—C3C | 1.312 (2) |
C9A—C10A | 1.371 (3) | O3C—H3C | 0.8200 |
C9A—H9A | 0.9300 | N1C—C6C | 1.301 (2) |
C10A—C11A | 1.364 (3) | N1C—N2C | 1.371 (2) |
C10A—H10A | 0.9300 | N2C—C7C | 1.393 (2) |
C11A—C12A | 1.377 (3) | N2C—H2C | 0.8836 |
C11A—H11A | 0.9300 | C1C—C2C | 1.434 (2) |
C12A—H12A | 0.9300 | C2C—C3C | 1.397 (3) |
C51A—H51A | 0.9600 | C2C—C6C | 1.464 (2) |
C51A—H51B | 0.9600 | C3C—C4C | 1.413 (3) |
C51A—H51C | 0.9600 | C4C—C5C | 1.332 (3) |
C61A—H61A | 0.9600 | C4C—H4C | 0.9300 |
C61A—H61B | 0.9600 | C5C—C51C | 1.482 (3) |
C61A—H61C | 0.9600 | C6C—C61C | 1.483 (3) |
O1B—C5B | 1.364 (2) | C7C—C12C | 1.389 (3) |
O1B—C1B | 1.395 (2) | C7C—C8C | 1.395 (3) |
O2B—C1B | 1.213 (2) | C8C—C9C | 1.380 (3) |
O3B—C3B | 1.291 (2) | C8C—H8C | 0.9300 |
O3B—H3B | 0.8200 | C9C—C10C | 1.375 (3) |
N1B—C6B | 1.298 (2) | C9C—H9C | 0.9300 |
N1B—N2B | 1.377 (2) | C10C—C11C | 1.381 (3) |
N2B—C7B | 1.395 (2) | C10C—H10C | 0.9300 |
N2B—H2B | 0.8876 | C11C—C12C | 1.378 (3) |
C1B—C2B | 1.425 (3) | C11C—H11C | 0.9300 |
C2B—C3B | 1.410 (3) | C12C—H12C | 0.9300 |
C2B—C6B | 1.456 (3) | C51C—H51G | 0.9600 |
C3B—C4B | 1.424 (3) | C51C—H51H | 0.9600 |
C4B—C5B | 1.319 (3) | C51C—H51I | 0.9600 |
C4B—H4B | 0.9300 | C61C—H61G | 0.9600 |
C5B—C51B | 1.488 (3) | C61C—H61H | 0.9600 |
C6B—C61B | 1.490 (3) | C61C—H61I | 0.9600 |
C5A—O1A—C1A | 122.99 (16) | C9B—C8B—C7B | 119.98 (19) |
C3A—O3A—H3A | 109.5 | C9B—C8B—H8B | 120.0 |
C6A—N1A—N2A | 120.67 (16) | C7B—C8B—H8B | 120.0 |
N1A—N2A—C7A | 118.33 (16) | C8B—C9B—C10B | 120.8 (2) |
N1A—N2A—H2A | 124.1 | C8B—C9B—H9B | 119.6 |
C7A—N2A—H2A | 117.4 | C10B—C9B—H9B | 119.6 |
O2A—C1A—O1A | 113.30 (17) | C11B—C10B—C9B | 119.1 (2) |
O2A—C1A—C2A | 128.92 (19) | C11B—C10B—H10B | 120.4 |
O1A—C1A—C2A | 117.78 (17) | C9B—C10B—H10B | 120.4 |
C3A—C2A—C1A | 117.67 (18) | C10B—C11B—C12B | 121.2 (2) |
C3A—C2A—C6A | 121.33 (17) | C10B—C11B—H11B | 119.4 |
C1A—C2A—C6A | 120.98 (17) | C12B—C11B—H11B | 119.4 |
O3A—C3A—C2A | 122.79 (18) | C11B—C12B—C7B | 119.71 (19) |
O3A—C3A—C4A | 116.01 (17) | C11B—C12B—H12B | 120.1 |
C2A—C3A—C4A | 121.20 (18) | C7B—C12B—H12B | 120.1 |
C5A—C4A—C3A | 119.67 (19) | C5B—C51B—H51D | 109.5 |
C5A—C4A—H4A | 120.2 | C5B—C51B—H51E | 109.5 |
C3A—C4A—H4A | 120.2 | H51D—C51B—H51E | 109.5 |
C4A—C5A—O1A | 120.67 (19) | C5B—C51B—H51F | 109.5 |
C4A—C5A—C51A | 127.8 (2) | H51D—C51B—H51F | 109.5 |
O1A—C5A—C51A | 111.53 (18) | H51E—C51B—H51F | 109.5 |
N1A—C6A—C2A | 114.80 (17) | C6B—C61B—H61D | 109.5 |
N1A—C6A—C61A | 121.34 (18) | C6B—C61B—H61E | 109.5 |
C2A—C6A—C61A | 123.85 (17) | H61D—C61B—H61E | 109.5 |
C12A—C7A—C8A | 118.87 (19) | C6B—C61B—H61F | 109.5 |
C12A—C7A—N2A | 122.85 (19) | H61D—C61B—H61F | 109.5 |
C8A—C7A—N2A | 118.28 (18) | H61E—C61B—H61F | 109.5 |
C9A—C8A—C7A | 119.7 (2) | C5C—O1C—C1C | 123.14 (14) |
C9A—C8A—H8A | 120.1 | C3C—O3C—H3C | 109.5 |
C7A—C8A—H8A | 120.1 | C6C—N1C—N2C | 120.41 (15) |
C10A—C9A—C8A | 121.3 (2) | N1C—N2C—C7C | 117.36 (15) |
C10A—C9A—H9A | 119.4 | N1C—N2C—H2C | 118.6 |
C8A—C9A—H9A | 119.4 | C7C—N2C—H2C | 116.7 |
C11A—C10A—C9A | 118.7 (2) | O2C—C1C—O1C | 113.59 (16) |
C11A—C10A—H10A | 120.7 | O2C—C1C—C2C | 128.63 (17) |
C9A—C10A—H10A | 120.7 | O1C—C1C—C2C | 117.78 (16) |
C10A—C11A—C12A | 121.4 (2) | C3C—C2C—C1C | 117.27 (16) |
C10A—C11A—H11A | 119.3 | C3C—C2C—C6C | 121.20 (16) |
C12A—C11A—H11A | 119.3 | C1C—C2C—C6C | 121.46 (17) |
C11A—C12A—C7A | 120.1 (2) | O3C—C3C—C2C | 121.98 (17) |
C11A—C12A—H12A | 120.0 | O3C—C3C—C4C | 116.86 (17) |
C7A—C12A—H12A | 120.0 | C2C—C3C—C4C | 121.16 (17) |
C5A—C51A—H51A | 109.5 | C5C—C4C—C3C | 120.34 (18) |
C5A—C51A—H51B | 109.5 | C5C—C4C—H4C | 119.8 |
H51A—C51A—H51B | 109.5 | C3C—C4C—H4C | 119.8 |
C5A—C51A—H51C | 109.5 | C4C—C5C—O1C | 120.07 (17) |
H51A—C51A—H51C | 109.5 | C4C—C5C—C51C | 128.09 (19) |
H51B—C51A—H51C | 109.5 | O1C—C5C—C51C | 111.83 (16) |
C6A—C61A—H61A | 109.5 | N1C—C6C—C2C | 115.30 (16) |
C6A—C61A—H61B | 109.5 | N1C—C6C—C61C | 120.92 (16) |
H61A—C61A—H61B | 109.5 | C2C—C6C—C61C | 123.78 (16) |
C6A—C61A—H61C | 109.5 | C12C—C7C—N2C | 122.11 (17) |
H61A—C61A—H61C | 109.5 | C12C—C7C—C8C | 118.92 (17) |
H61B—C61A—H61C | 109.5 | N2C—C7C—C8C | 118.91 (17) |
C5B—O1B—C1B | 122.75 (15) | C9C—C8C—C7C | 120.1 (2) |
C3B—O3B—H3B | 109.5 | C9C—C8C—H8C | 119.9 |
C6B—N1B—N2B | 121.79 (16) | C7C—C8C—H8C | 119.9 |
N1B—N2B—C7B | 115.71 (15) | C10C—C9C—C8C | 120.96 (19) |
N1B—N2B—H2B | 117.2 | C10C—C9C—H9C | 119.5 |
C7B—N2B—H2B | 115.3 | C8C—C9C—H9C | 119.5 |
O2B—C1B—O1B | 113.71 (17) | C9C—C10C—C11C | 118.81 (19) |
O2B—C1B—C2B | 128.52 (18) | C9C—C10C—H10C | 120.6 |
O1B—C1B—C2B | 117.77 (16) | C11C—C10C—H10C | 120.6 |
C3B—C2B—C1B | 117.97 (17) | C12C—C11C—C10C | 121.3 (2) |
C3B—C2B—C6B | 120.79 (17) | C12C—C11C—H11C | 119.4 |
C1B—C2B—C6B | 121.21 (17) | C10C—C11C—H11C | 119.4 |
O3B—C3B—C2B | 122.47 (18) | C11C—C12C—C7C | 119.90 (18) |
O3B—C3B—C4B | 117.34 (17) | C11C—C12C—H12C | 120.1 |
C2B—C3B—C4B | 120.19 (18) | C7C—C12C—H12C | 120.1 |
C5B—C4B—C3B | 120.34 (19) | C5C—C51C—H51G | 109.5 |
C5B—C4B—H4B | 119.8 | C5C—C51C—H51H | 109.5 |
C3B—C4B—H4B | 119.8 | H51G—C51C—H51H | 109.5 |
C4B—C5B—O1B | 120.80 (18) | C5C—C51C—H51I | 109.5 |
C4B—C5B—C51B | 126.72 (19) | H51G—C51C—H51I | 109.5 |
O1B—C5B—C51B | 112.47 (18) | H51H—C51C—H51I | 109.5 |
N1B—C6B—C2B | 114.76 (17) | C6C—C61C—H61G | 109.5 |
N1B—C6B—C61B | 120.29 (17) | C6C—C61C—H61H | 109.5 |
C2B—C6B—C61B | 124.95 (17) | H61G—C61C—H61H | 109.5 |
C8B—C7B—C12B | 119.23 (18) | C6C—C61C—H61I | 109.5 |
C8B—C7B—N2B | 118.78 (17) | H61G—C61C—H61I | 109.5 |
C12B—C7B—N2B | 121.92 (17) | H61H—C61C—H61I | 109.5 |
Cg2, Cg4 ad Cg6 are the centroids of rings C7A–C12A, C7B–C12B and C7C–C12C, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3A···N1A | 0.82 | 1.74 | 2.469 (2) | 147 |
O3B—H3B···N1B | 0.82 | 1.71 | 2.448 (2) | 148 |
N2A—H2A···O2Ci | 0.91 | 2.20 | 3.099 (2) | 170 |
N2B—H2B···O2Ai | 0.89 | 2.13 | 2.994 (2) | 165 |
O3C—H3C···N1C | 0.82 | 1.73 | 2.462 (2) | 148 |
N2C—H2C···O2B | 0.88 | 2.19 | 3.028 (2) | 157 |
C8B—H8B···O1Ai | 0.93 | 2.53 | 3.438 (2) | 165 |
C8C—H8C···O1B | 0.93 | 2.58 | 3.473 (2) | 162 |
C10A—H10A···O3Bii | 0.93 | 2.58 | 3.294 (3) | 134 |
C51A—H51B···Cg4iii | 0.96 | 2.84 | 3.729 (3) | 154 |
C51B—H51F···Cg2iii | 0.96 | 2.62 | 3.436 (3) | 143 |
C51C—H51G···Cg6iv | 0.96 | 2.95 | 3.729 (2) | 139 |
C51C—H51H···Cg6v | 0.96 | 2.62 | 3.516 (2) | 156 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+3/2, −y−1/2, −z+2; (iii) x, −y, z−1/2; (iv) −x+2, −y+1, −z+2; (v) −x+2, y, −z+5/2. |
Cg2, Cg4 ad Cg6 are the centroids of rings C7A–C12A, C7B–C12B and C7C–C12C, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3A···N1A | 0.82 | 1.74 | 2.469 (2) | 147.0 |
O3B—H3B···N1B | 0.82 | 1.71 | 2.448 (2) | 148.0 |
N2A—H2A···O2Ci | 0.91 | 2.20 | 3.099 (2) | 169.5 |
N2B—H2B···O2Ai | 0.89 | 2.13 | 2.994 (2) | 164.6 |
O3C—H3C···N1C | 0.82 | 1.73 | 2.462 (2) | 148.2 |
N2C—H2C···O2B | 0.88 | 2.19 | 3.028 (2) | 157.3 |
C8B—H8B···O1Ai | 0.93 | 2.53 | 3.438 (2) | 165 |
C8C—H8C···O1B | 0.93 | 2.58 | 3.473 (2) | 162 |
C10A—H10A···O3Bii | 0.93 | 2.58 | 3.294 (3) | 134 |
C51A—H51B···Cg4iii | 0.96 | 2.84 | 3.729 (3) | 154 |
C51B—H51F···Cg2iii | 0.96 | 2.62 | 3.436 (3) | 143 |
C51C—H51G···Cg6iv | 0.96 | 2.95 | 3.729 (2) | 139 |
C51C—H51H···Cg6v | 0.96 | 2.62 | 3.516 (2) | 156 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+3/2, −y−1/2, −z+2; (iii) x, −y, z−1/2; (iv) −x+2, −y+1, −z+2; (v) −x+2, y, −z+5/2. |
Experimental details
Crystal data | |
Chemical formula | C14H14N2O3 |
Mr | 258.27 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 30.1064 (12), 17.5911 (7), 13.7937 (8) |
β (°) | 92.613 (4) |
V (Å3) | 7297.6 (6) |
Z | 24 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.1 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Agilent Xcalibur Sapphire 1 (long nozzle) |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.725, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37468, 7444, 4849 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.125, 1.02 |
No. of reflections | 7444 |
No. of parameters | 524 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.21 |
Computer programs: CrysAlis PRO (Agilent, 2011), SIR97 (Altomare et al., 1999), Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge support from the Algerian agency MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique), and the DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique),
References
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