Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o564-o565
https://doi.org/10.1107/S2056989015012840

Crystal structure of (E)-4-hy­dr­oxy-3-{1-[(4-hy­dr­oxy­phen­yl)imino]­eth­yl}-6-methyl-2H-pyran-2-one

Amel Djedouani,a Sihem Boufas,b* Franck Cleymand,c Michel Françoisc and Solenne Fleutotc

aLaboratoire de Physicochimie Analytique et Cristallochimie de Matériaux, Organométalliques et Biomoléculaires, Université de Constantine 1, 25000 Constantine, Algeria, bLaboratoire de Génie Mécanique et Matériaux, Faculté de Technologie, Université 20 Aout 1955, 21000 Skikda, Algeria, and cInstitut Jean Lamour UMR 7198, Parc de Saurupt, CS 14234 F 54042 Nancy, France
*Correspondence e-mail: boufas_sihem@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 July 2015; accepted 3 July 2015; online 11 July 2015)

In the title Schiff base, C14H13NO4, which adopts the phenol–imine tautomeric form, the dihedral angle between the planes of the benzene and heterocyclic (r.m.s. deviation = 0.037 Å) rings is 53.31 (11)°. An intra­molecular O—H⋯N hydrogen bond closes an S(6) ring. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds to generate C(11) chains propagating in the [010] direction. A weak C—H⋯O link is also observed, leading to the formation of R55(32) rings extending parallel to the (101) plane.

CCDC reference: 1410367

Similar articles

1. Related literature

For photochromic and thermochromic properties of hy­droxy Schiff bases, see: Garnovskii et al. (1993[Garnovskii, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1-69.]); Hadjoudis et al. (2004[Hadjoudis, E., Rontoyianni, A., Ambroziak, K., Dziembowska, T. & Mavridis, I. M. (2004). J. Photochem. Photobiol. Chem. 162, 521-530.]). For potential materials for optical memory and switch devices, see: Zhao et al. (2007[Zhao, L., Hou, Q., Sui, D., Wang, Y. & Jiang, S. (2007). Spectrochim. Acta A Mol. Biomol. Spectrosc. 67, 1120-1125.]). For proton-transfer processes, see: Lussier et al. (1987[Lussier, L. S., Sandorfy, C., Le Thanh Hoa & Vocelle, D. (1987). J. Phys. Chem. 91, 2282-2287.]). For Schiff base structures, see: Djedouani et al. (2007[Djedouani, A., Bendaas, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2007). Acta Cryst. E63, o1271-o1273.], 2008[Djedouani, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2008). Acta Cryst. E64, o1785.]). For Schiff base bond lengths and angles, see: Girija & Begum (2004[Girija, C. R. & Begum, N. S. (2004). Acta Cryst. E60, o535-o536.]); Girija et al. (2004[Girija, C. R., Begum, N. S., Sridhar, M. A., Lokanath, N. K. & Prasad, J. S. (2004). Acta Cryst. E60, o586-o588.]); Bai & Jing (2007[Bai, Z.-C. & Jing, Z.-L. (2007). Acta Cryst. E63, o3822.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C14H13NO4

  • Mr = 259.26

  • Monoclinic, P 21 /c

  • a = 7.8730 (5) Å

  • b = 11.7930 (8) Å

  • c = 13.5330 (8) Å

  • β = 99.896 (2)°

  • V = 1237.79 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.10 × 0.06 × 0.03 mm

2.2. Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.875, Tmax = 0.947

  • 17976 measured reflections

  • 2582 independent reflections

  • 2061 reflections with I > 2σ(I)

  • Rint = 0.026

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.148

  • S = 1.07

  • 2582 reflections

  • 173 parameters

  • All H-atom parameters refined

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.83 2.560 (2) 147
O2—H2⋯O1i 0.82 1.90 2.710 (2) 169
C12—H12B⋯O3ii 0.96 2.55 3.137 (3) 120
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: COLLECT (Nonius, 2002[Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: OLEX2.refine (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).

Supporting information

CCDC reference: 1410367

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012840/hb7460sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012840/hb7460Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015012840/hb7460Isup3.cml

checkCIF report


Comment top

Hydroxy Schiff bases have been extensively studied due to their biological, photochromic and thermochromic properties (Garnovskii et al., 1993; Hadjoudis et al., 2004). They are potential materials for optical memory and switch devices (Zhao et al., 2007). Proton transfer in these compounds forms the basis for an explanation of the mechanisms of various biological processes where proton transfer is the rate-determining step (Lussier et al., 1987). In general, O-hydroxy Schiff bases exhibit two possible tautomeric forms, the phenol-imine (or benzenoid) and ketoamine (or quinoid) forms. Depending on the tautomers, two types of intra-molecular hydrogen bonds are possible: O—H···N in benzenoid and N—H···O in quinoid tautomers.

As part of our ongoing studies of Schiff bases (Djedouani et al., 2007, 2008), we now describe the synthesis and the structure of the title compound, which takes the form phenol-imine and complete a six-membered pseudocycle via an intramolecular O—H····O hydrogen bond.

The dehydroacetic acid ring and phenyl ring are almost planer with r.m.s deviation for the mean plane are 0.0260 and 0.0027 respectively. The dihedral angle between the two rings is 53.30 (0.05) °. The two torsional angles τ1 (N1—C5—C14—C4) and τ2 (C5—N1—C1—C6) defining the confirmation of the molecule.

The N1—C5 distance of 1.324 (2) Å agree with similar bond in related compounds (Girija & Begum, 2004; Girija et al. 2004), slightly longer than a typical C=N bond (1.283 (4) Å) (Bai & Jing, 2007); but much shorter than the single carbon-nitrogen bond (Table. 1), N1—C1=1.432 (3) Å because of the resonance. The carbon-carbon bond connecting the phenol and imine groups exhibits intermediate distances between a single and a double bond and agree well with those observed in other azomethines. The C5—N1—C14 and C14—C5—N1 bond angle of 117.70 (2)° and 117.47 () ° respectively in the Schiff base ligand are smaller than typical hexagonal of 120°. This is due to the effect of substitution on O of pyron & OH of the DHA ring.

In the crystal, molecules are aligned head to foot along b axis, in columns along to [0 0 1] axis and the structure is stabilized by an O—H···O hydrogen bond and another weak C—H···O interaction, leading to the formation of R55(32) rings extending parallel to the (101) plane (Fig. 2, Table.1).

Related literature top

For photochromic and thermochromic properties of hydroxy Schiff bases, see: Garnovskii et al. (1993); Hadjoudis et al. (2004). For potential materials for optical memory and switch devices, see: Zhao et al. (2007). For proton-transfer processes, see: Lussier et al. (1987). For Schiff base structures, see: Djedouani et al. (2007, 2008) For Schiff base bond lengths and angles, see: Girija & Begum (2004); Girija et al. (2004); Bai & Jing (2007).

Experimental top

Compound (I) was prepared by refluxing a mixture of a solution containing dehydroacetic acid (0.01 mmol) and para-4-aminophenol (0.01 mmol) in ethanol (40 ml). The reaction mixture was stirred for 2 h under reflux and left to cool. Yellow crystals grew after a few days.

Refinement top

C—H and O—H hydrogen atoms were placed in calculated positions and refined as riding atoms with C—H distances of 0.93 Å with Uiso(H) = 1.2Ueq(C) and O—H distances of 0.82 Å, with Uiso(H) = 1.2Ueq(N).

The methyl H atoms were constrained to an ideal geometry (C—H = 0.96 Å) with Uiso(H) = 1.2Ueq(C), but were allowed to rotate freely about the C—C bonds.

Structure description top

Hydroxy Schiff bases have been extensively studied due to their biological, photochromic and thermochromic properties (Garnovskii et al., 1993; Hadjoudis et al., 2004). They are potential materials for optical memory and switch devices (Zhao et al., 2007). Proton transfer in these compounds forms the basis for an explanation of the mechanisms of various biological processes where proton transfer is the rate-determining step (Lussier et al., 1987). In general, O-hydroxy Schiff bases exhibit two possible tautomeric forms, the phenol-imine (or benzenoid) and ketoamine (or quinoid) forms. Depending on the tautomers, two types of intra-molecular hydrogen bonds are possible: O—H···N in benzenoid and N—H···O in quinoid tautomers.

As part of our ongoing studies of Schiff bases (Djedouani et al., 2007, 2008), we now describe the synthesis and the structure of the title compound, which takes the form phenol-imine and complete a six-membered pseudocycle via an intramolecular O—H····O hydrogen bond.

The dehydroacetic acid ring and phenyl ring are almost planer with r.m.s deviation for the mean plane are 0.0260 and 0.0027 respectively. The dihedral angle between the two rings is 53.30 (0.05) °. The two torsional angles τ1 (N1—C5—C14—C4) and τ2 (C5—N1—C1—C6) defining the confirmation of the molecule.

The N1—C5 distance of 1.324 (2) Å agree with similar bond in related compounds (Girija & Begum, 2004; Girija et al. 2004), slightly longer than a typical C=N bond (1.283 (4) Å) (Bai & Jing, 2007); but much shorter than the single carbon-nitrogen bond (Table. 1), N1—C1=1.432 (3) Å because of the resonance. The carbon-carbon bond connecting the phenol and imine groups exhibits intermediate distances between a single and a double bond and agree well with those observed in other azomethines. The C5—N1—C14 and C14—C5—N1 bond angle of 117.70 (2)° and 117.47 () ° respectively in the Schiff base ligand are smaller than typical hexagonal of 120°. This is due to the effect of substitution on O of pyron & OH of the DHA ring.

In the crystal, molecules are aligned head to foot along b axis, in columns along to [0 0 1] axis and the structure is stabilized by an O—H···O hydrogen bond and another weak C—H···O interaction, leading to the formation of R55(32) rings extending parallel to the (101) plane (Fig. 2, Table.1).

For photochromic and thermochromic properties of hydroxy Schiff bases, see: Garnovskii et al. (1993); Hadjoudis et al. (2004). For potential materials for optical memory and switch devices, see: Zhao et al. (2007). For proton-transfer processes, see: Lussier et al. (1987). For Schiff base structures, see: Djedouani et al. (2007, 2008) For Schiff base bond lengths and angles, see: Girija & Begum (2004); Girija et al. (2004); Bai & Jing (2007).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: olex2.refine (Dolomanov et al., 2009); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The structure of the title compound in 50% probability ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of S(6) rings with dashed red lines. C—H···O and O—H···O hydrogen bonds are shown as blue dashed lines.
(E)-4-hydroxy-3-{1-[(4-hydroxyphenyl)imino]ethyl}-6-methyl-2H-pyran-2-one top
Crystal data top
C14H13NO4F(000) = 544.3271
Mr = 259.26Dx = 1.391 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 0 reflections
a = 7.8730 (5) Åθ = 2.9–27.5°
b = 11.7930 (8) ŵ = 0.10 mm−1
c = 13.5330 (8) ÅT = 293 K
β = 99.896 (2)°Block, yellow
V = 1237.79 (14) Å30.10 × 0.06 × 0.03 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer		2582 independent reflections
Radiation source: Enraf–Nonius FR5902061 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 9 pixels mm-1θmax = 26.7°, θmin = 2.3°
CCD rotation images, thin slices scansh = −9→9
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		k = −14→14
Tmin = 0.875, Tmax = 0.947l = −17→17
17976 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.6848P]
where P = (Fo2 + 2Fc2)/3
2582 reflections(Δ/σ)max = 0.005
173 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C14H13NO4V = 1237.79 (14) Å3
Mr = 259.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8730 (5) ŵ = 0.10 mm−1
b = 11.7930 (8) ÅT = 293 K
c = 13.5330 (8) Å0.10 × 0.06 × 0.03 mm
β = 99.896 (2)°
Data collection top
Nonius KappaCCD
diffractometer		2582 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		2061 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 0.947Rint = 0.026
17976 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.148All H-atom parameters refined
S = 1.07Δρmax = 0.54 e Å−3
2582 reflectionsΔρmin = −0.38 e Å−3
173 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6637 (2)−0.08723 (12)0.50633 (10)0.0520 (4)
H10.6696 (2)−0.05535 (12)0.45317 (10)0.0779 (6)*
O20.4993 (2)0.21003 (13)−0.00201 (10)0.0543 (4)
H20.4624 (2)0.27519 (13)−0.00450 (10)0.0815 (7)*
O31.0343 (3)0.20593 (17)0.65333 (13)0.0814 (7)
O40.92760 (19)0.08216 (12)0.74439 (9)0.0443 (4)
C10.6821 (3)0.11371 (17)0.29043 (13)0.0390 (4)
C20.7568 (3)−0.07161 (18)0.67874 (15)0.0444 (5)
H2a0.7031 (3)−0.13959 (18)0.68968 (15)0.0533 (6)*
C30.6279 (3)0.07382 (18)0.11415 (14)0.0433 (5)
H30.6333 (3)0.02421 (18)0.06136 (14)0.0520 (6)*
C40.7488 (3)−0.03156 (16)0.57810 (14)0.0391 (4)
C50.8305 (3)0.12191 (16)0.46720 (14)0.0382 (4)
C60.6138 (3)0.22135 (17)0.27136 (14)0.0416 (5)
H60.6089 (3)0.27092 (17)0.32425 (14)0.0499 (6)*
C70.5531 (3)0.25514 (17)0.17428 (14)0.0416 (5)
H70.5074 (3)0.32751 (17)0.16191 (14)0.0499 (6)*
C80.8390 (3)−0.01396 (17)0.75665 (14)0.0407 (5)
C90.9259 (3)0.22691 (19)0.44950 (16)0.0489 (5)
H9a0.9215 (18)0.2372 (8)0.37874 (17)0.0733 (8)*
H9b0.8738 (13)0.2909 (3)0.4764 (11)0.0733 (8)*
H9c1.0438 (6)0.2203 (6)0.4820 (10)0.0733 (8)*
C100.5598 (3)0.18172 (17)0.09476 (13)0.0389 (4)
C110.9398 (3)0.12553 (18)0.65006 (15)0.0454 (5)
C120.8492 (3)−0.0416 (2)0.86465 (15)0.0554 (6)
H12a0.9678 (4)−0.0434 (15)0.8967 (3)0.0831 (9)*
H12b0.789 (2)0.0151 (9)0.8959 (3)0.0831 (9)*
H12c0.797 (2)−0.1144 (7)0.87109 (15)0.0831 (9)*
C130.6877 (3)0.03998 (17)0.21150 (15)0.0419 (5)
H130.7319 (3)−0.03271 (17)0.22414 (15)0.0502 (6)*
C140.8397 (2)0.07122 (16)0.56378 (13)0.0368 (4)
N10.7321 (2)0.07168 (14)0.39048 (12)0.0434 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0748 (11)0.0408 (8)0.0347 (7)−0.0120 (7)−0.0066 (7)0.0022 (6)
O20.0822 (11)0.0507 (9)0.0265 (7)0.0122 (8)−0.0009 (7)0.0018 (6)
O30.1131 (16)0.0775 (13)0.0444 (9)−0.0536 (12)−0.0125 (9)0.0064 (9)
O40.0563 (9)0.0434 (8)0.0295 (7)−0.0021 (6)−0.0029 (6)−0.0003 (6)
C10.0454 (11)0.0404 (10)0.0286 (9)−0.0016 (8)−0.0009 (7)0.0027 (8)
C20.0565 (13)0.0373 (10)0.0383 (10)−0.0024 (9)0.0051 (9)0.0042 (8)
C30.0508 (12)0.0445 (11)0.0329 (10)0.0055 (9)0.0021 (8)−0.0065 (8)
C40.0466 (11)0.0347 (10)0.0332 (9)0.0032 (8)−0.0009 (8)−0.0006 (8)
C50.0431 (10)0.0367 (10)0.0329 (9)0.0046 (8)0.0012 (8)0.0004 (8)
C60.0557 (12)0.0394 (10)0.0290 (9)0.0000 (9)0.0052 (8)−0.0029 (8)
C70.0532 (12)0.0359 (10)0.0343 (10)0.0040 (9)0.0036 (8)0.0028 (8)
C80.0475 (11)0.0389 (10)0.0346 (10)0.0077 (8)0.0046 (8)0.0027 (8)
C90.0536 (13)0.0506 (12)0.0397 (11)−0.0060 (10)0.0007 (9)0.0079 (9)
C100.0451 (11)0.0425 (11)0.0275 (9)0.0004 (8)0.0018 (7)0.0032 (8)
C110.0555 (13)0.0423 (11)0.0348 (10)−0.0052 (10)−0.0028 (9)0.0032 (8)
C120.0773 (16)0.0557 (14)0.0329 (11)0.0044 (12)0.0088 (10)0.0034 (9)
C130.0462 (11)0.0379 (10)0.0385 (10)0.0066 (8)−0.0008 (8)0.0005 (8)
C140.0439 (11)0.0336 (9)0.0306 (9)0.0029 (8)−0.0002 (8)0.0021 (7)
N10.0560 (10)0.0414 (9)0.0290 (8)−0.0014 (8)−0.0033 (7)0.0036 (7)
Geometric parameters (Å, º) top
O1—H10.82C5—C91.489 (3)
O1—C41.265 (2)C5—C141.428 (3)
O2—H20.82C5—N11.324 (2)
O2—C101.356 (2)C6—H60.93
O3—C111.201 (3)C6—C71.377 (3)
O4—C81.356 (2)C7—H70.93
O4—C111.394 (2)C7—C101.389 (3)
C1—C61.385 (3)C8—C121.486 (3)
C1—C131.384 (3)C9—H9a0.96
C1—N11.432 (2)C9—H9b0.96
C2—H2a0.93C9—H9c0.96
C2—C41.433 (3)C11—C141.442 (3)
C2—C81.326 (3)C12—H12a0.96
C3—H30.93C12—H12b0.96
C3—C101.388 (3)C12—H12c0.96
C3—C131.380 (3)C13—H130.93
C4—C141.438 (3)
C4—O1—H1109.5C12—C8—C2127.3 (2)
C10—O2—H2109.5H9a—C9—C5109.5
C11—O4—C8122.46 (15)H9b—C9—C5109.5
C13—C1—C6119.66 (17)H9b—C9—H9a109.5
N1—C1—C6121.88 (17)H9c—C9—C5109.5
N1—C1—C13118.18 (18)H9c—C9—H9a109.5
C4—C2—H2a119.25 (12)H9c—C9—H9b109.5
C8—C2—H2a119.25 (12)C3—C10—O2117.93 (17)
C8—C2—C4121.5 (2)C7—C10—O2122.75 (18)
C10—C3—H3119.90 (11)C7—C10—C3119.31 (17)
C13—C3—H3119.90 (12)O4—C11—O3113.30 (18)
C13—C3—C10120.19 (18)C14—C11—O3129.00 (19)
C2—C4—O1119.33 (18)C14—C11—O4117.69 (18)
C14—C4—O1122.99 (17)H12a—C12—C8109.5
C14—C4—C2117.68 (17)H12b—C12—C8109.5
C14—C5—C9123.23 (17)H12b—C12—H12a109.5
N1—C5—C9119.29 (17)H12c—C12—C8109.5
N1—C5—C14117.48 (18)H12c—C12—H12a109.5
H6—C6—C1119.91 (11)H12c—C12—H12b109.5
C7—C6—C1120.17 (18)C3—C13—C1120.30 (18)
C7—C6—H6119.91 (12)H13—C13—C1119.85 (11)
H7—C7—C6119.82 (12)H13—C13—C3119.85 (12)
C10—C7—C6120.36 (18)C5—C14—C4121.89 (17)
C10—C7—H7119.82 (11)C11—C14—C4118.74 (17)
C2—C8—O4121.50 (18)C11—C14—C5119.35 (18)
C12—C8—O4111.21 (18)C5—N1—C1127.99 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.560 (2)147
O2—H2···O1i0.821.902.710 (2)169
C12—H12B···O3ii0.962.553.137 (3)120
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.560 (2)147
O2—H2···O1i0.821.902.710 (2)169
C12—H12B···O3ii0.962.553.137 (3)120
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+3/2.
 

Acknowledgements

This work was supported by Université Constantine 1, DZ-25000, Constantine, Algeria.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBai, Z.-C. & Jing, Z.-L. (2007). Acta Cryst. E63, o3822.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationDjedouani, A., Bendaas, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2007). Acta Cryst. E63, o1271–o1273.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationDjedouani, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2008). Acta Cryst. E64, o1785.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationDuisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationGarnovskii, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69.  CrossRef CAS Web of Science Google Scholar
 First citationGirija, C. R. & Begum, N. S. (2004). Acta Cryst. E60, o535–o536.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGirija, C. R., Begum, N. S., Sridhar, M. A., Lokanath, N. K. & Prasad, J. S. (2004). Acta Cryst. E60, o586–o588.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHadjoudis, E., Rontoyianni, A., Ambroziak, K., Dziembowska, T. & Mavridis, I. M. (2004). J. Photochem. Photobiol. Chem. 162, 521–530.  Web of Science CSD CrossRef CAS Google Scholar
 First citationLussier, L. S., Sandorfy, C., Le Thanh Hoa & Vocelle, D. (1987). J. Phys. Chem. 91, 2282–2287.  Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals Google Scholar
 First citationNonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationZhao, L., Hou, Q., Sui, D., Wang, Y. & Jiang, S. (2007). Spectrochim. Acta A Mol. Biomol. Spectrosc. 67, 1120–1125.  Web of Science CrossRef PubMed 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o564-o565
https://doi.org/10.1107/S2056989015012840
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS