3-Meth­oxy-2-[(E)-(4-meth­oxy­phen­yl)imino­meth­yl]phenol

Özdemir Tari, G.; Işık, Ş.; Özkan, R.; Alaman Ağar, A.

doi:10.1107/S1600536811000596

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o343-o344

doi:10.1107/S1600536811000596

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3-Methoxy-2-[(E)-(4-methoxyphenyl)iminomethyl]phenol

Gonca Özdemir Tari,^a Şamil Işık,^a Ramazan Özkan ^b and Ayşen Alaman Ağar ^b ^*

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139 Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139 Samsun, Turkey
^*Correspondence e-mail: gozdemir@omu.edu.tr

(Received 28 December 2010; accepted 5 January 2011; online 12 January 2011)

The title compound, C₁₅H₁₅NO₃, adopts the enol–imine tautomeric form. The two rings are twisted with respect to each other, making a dihedral angle of 44.08 (5)°. The 3-methoxy-2-[(E)-(4-methoxyphenyl)-iminomethyl]phenol unit is almost planar, the largest deviation from the mean plane being 0.047 (2) Å. Such a planar conformation might be related to the occurrence of an intramolecular O—H⋯N hydrogen bond. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into sheets parallel to (010). These sheets are interconnected by weak C—H⋯π interactions.

Related literature

For background to the properties and uses of Schiff bases, see: Barton & Ollis (1979 ); Layer (1963 ); Ingold (1969 ); Cohen et al. (1964 ); Taggi et al. (2002 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Bernstein et al. (1995 ). For related structures, see: Özdemir Tarı et al. (2010 ); Şahin et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₅NO₃
M_r = 257.28
Monoclinic, P 2₁ /c
a = 14.2658 (8) Å
b = 14.1553 (11) Å
c = 6.5893 (17) Å
β = 96.398 (9)°
V = 1322.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.65 × 0.32 × 0.14 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe, 2002) T_min = 0.991, T_max = 0.997
7244 measured reflections
2585 independent reflections
1622 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.122
S = 1.04
2585 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1—C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.93	2.60	3.428 (3)	149
C14—H14A⋯O1ⁱⁱ	0.96	2.49	3.412 (3)	162
O2—H2A⋯N1	0.82	1.87	2.590 (2)	146
C5—H5⋯Cg1ⁱⁱⁱ	0.93	2.80	3.486 (2)	132
Symmetry codes: (i) x, y, z-1; (ii) x-1, y, z-1; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000596/dn2646sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000596/dn2646Isup2.hkl

checkCIF report

Comment top

Schiff bases are used as starting materials in the synthesis of important drugs, such as antibiotics and antiallergic, antiphlogistic, and antitumor substances (Barton et al., 1979; Layer, 1963; Ingold 1969). On the industrial scale, they have a wide range of applications, such as dyes and pigments (Taggi et al., 2002). There are two characteristic properties of Schiff bases, viz. Photochromism and thermochromism (Cohen et al., 1964). In general, Schiff bases display two possible tautomeric forms, the phenol-imine (OH) and the keto-amine (NH) forms. Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in Schiff bases: O—H···N in phenol-imine (Özdemir Tarı et al., 2010) and N—H···O in keto-amine tautomers (Şahin et al., 2005). Another form of the Schiff base compounds is also known as zwitterion having an ionic intramolecular hydrogen bond (N⁺—H···O^-) and this form is rarely seen in the solid state (Özdemir Tarı et al., 2010).

The title compound, C₁₅H₁₅O₃N₁, adopts the enol-imine tautomeric form. The C7=N1 [1.278 (3) Å] and C8=N1 [1.419 (2) Å] bond distances are of double-bond character, whereas, C6—O2 [1.356 (2) Å] distance is single bond. These distances are similar to that reported in the literature [1.269 (8) Å] and [1.397 (7) Å] for C=N and [1.332 (8) Å] for C—O respectively (Özdemir Tarı et al., 2010).

The two phenyl rings are twisted with respect to each other making dihedral angle of 44.08 (5)° (Fig. 1). The 4-methoxyphenylimino)phenol moiety is planar with the largest deviation from the mean plane being 0.047 (2)Å at C7. Such planar conformation might be related to the occurrence of the O—H···N intramolecular hydrogen bond (Fig. 1, Table 1). This intramolecular N—H···O hydrogen bond results in the formation of an S(6) ring (Etter et al., 1990; Bernstein et al., 1995).

Intermolecular C—H···O hydrogen bonds link the molecules forming sheets parallel to the (0 1 0) plane (Fig. 2, Table 1). These sheets are interconnected by weak C—H···π interactions (Table 1, Cg1 is the centroid of the C1—C6 phenyl ring).

Related literature top

For background to the properties and uses of Schiff bases, see: Barton & Ollis (1979); Layer (1963); Ingold (1969); Cohen et al. (1964); Taggi et al. (2002). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995). For related structures, see: Özdemir Tarı et al. (2010); Şahin et al. (2005).

Experimental top

(E)-3-methoxy-2-((4-methoxyphenylimino)methyl)phenol was prepared by refluxing a mixture of a solution containing 2-hydroxy-6- methoxybenzaldehyde (15.2 mg, o.1 mmol) in ethanol (30 ml) and a solution containing 4-methoxyaniline (12.3 mg, 0.1 mmol) in ethanol (20 ml). The reaction mixture was stirred for 2 h under reflux. Single crystals of the title compound for x-ray analysis were obtained by slow evaporation of an ethanol solution (yield 72%; m.p 346–348 K).

Computing details top

Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA (Stoe, 2002); data reduction: X-RED32 (Stoe, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small sphere of arbitrary radii. Intramolecular H bond is shown as dashed line.
	Fig. 2. The crystal packing of the title compound showing the formation of sheets parallel to the (0 1 0) plane. H bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

3-Methoxy-2-[(E)-(4-methoxyphenyl)iminomethyl]phenol top

Crystal data top

C₁₅H₁₅NO₃	F(000) = 544
M_r = 257.28	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12079 reflections
a = 14.2658 (8) Å	θ = 1.4–27.2°
b = 14.1553 (11) Å	µ = 0.09 mm⁻¹
c = 6.5893 (17) Å	T = 293 K
β = 96.398 (9)°	Prism, brown
V = 1322.3 (4) Å³	0.65 × 0.32 × 0.14 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	2585 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 1.4°
ϕ scan rotation method	h = −16→17
Absorption correction: integration (X-RED32; Stoe, 2002)	k = −17→17
T_min = 0.991, T_max = 0.997	l = −8→6
7244 measured reflections

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0524P)² + 0.1038P] where P = (F_o² + 2F_c²)/3
2585 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₅NO₃	V = 1322.3 (4) Å³
M_r = 257.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2658 (8) Å	µ = 0.09 mm⁻¹
b = 14.1553 (11) Å	T = 293 K
c = 6.5893 (17) Å	0.65 × 0.32 × 0.14 mm
β = 96.398 (9)°

Data collection top

Stoe IPDS 2 diffractometer	2585 independent reflections
Absorption correction: integration (X-RED32; Stoe, 2002)	1622 reflections with I > 2σ(I)
T_min = 0.991, T_max = 0.997	R_int = 0.032
7244 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	Δρ_max = 0.11 e Å⁻³
2585 reflections	Δρ_min = −0.19 e Å⁻³
172 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.20529 (13)	0.11619 (13)	0.4013 (3)	0.0443 (5)
C2	0.29338 (14)	0.10131 (14)	0.3295 (3)	0.0483 (5)
H2	0.2959	0.0793	0.1972	0.058*
C3	0.37566 (14)	0.11898 (15)	0.4526 (3)	0.0516 (5)
C4	0.37125 (16)	0.15062 (15)	0.6515 (3)	0.0548 (6)
H4	0.4268	0.1626	0.7353	0.066*
C5	0.28635 (16)	0.16440 (15)	0.7254 (3)	0.0542 (6)
H5	0.2848	0.1854	0.8588	0.065*
C6	0.20294 (15)	0.14735 (14)	0.6034 (3)	0.0479 (5)
C7	0.11923 (14)	0.10451 (13)	0.2639 (3)	0.0481 (5)
H7	0.1229	0.0900	0.1274	0.058*
C8	−0.04619 (13)	0.11307 (14)	0.1930 (3)	0.0459 (5)
C9	−0.12676 (15)	0.07751 (15)	0.2668 (4)	0.0544 (6)
H9	−0.1226	0.0522	0.3977	0.065*
C10	−0.21198 (15)	0.07926 (15)	0.1495 (4)	0.0553 (6)
H10	−0.2648	0.0535	0.1995	0.066*
C11	−0.22005 (14)	0.11941 (14)	−0.0446 (4)	0.0512 (5)
C12	−0.14058 (15)	0.15559 (16)	−0.1200 (4)	0.0561 (6)
H12	−0.1452	0.1823	−0.2497	0.067*
C13	−0.05435 (15)	0.15172 (15)	−0.0012 (3)	0.0537 (6)
H13	−0.0010	0.1755	−0.0526	0.064*
C14	−0.3216 (2)	0.1629 (2)	−0.3428 (5)	0.0908 (9)
H14A	−0.3868	0.1590	−0.3970	0.136*
H14B	−0.2837	0.1297	−0.4310	0.136*
H14C	−0.3026	0.2280	−0.3338	0.136*
C15	0.47450 (18)	0.0772 (2)	0.1985 (4)	0.0881 (9)
H15A	0.5402	0.0742	0.1795	0.132*
H15B	0.4427	0.1196	0.1000	0.132*
H15C	0.4472	0.0153	0.1810	0.132*
N1	0.03849 (12)	0.11390 (12)	0.3283 (3)	0.0496 (4)
O1	0.46496 (10)	0.10987 (13)	0.3953 (3)	0.0752 (5)
O2	0.12069 (11)	0.16290 (11)	0.6830 (2)	0.0636 (5)
H2A	0.0763	0.1500	0.5975	0.095*
O3	−0.30930 (10)	0.12168 (12)	−0.1453 (3)	0.0662 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0417 (11)	0.0426 (10)	0.0480 (12)	−0.0004 (9)	0.0020 (9)	−0.0004 (9)
C2	0.0481 (12)	0.0525 (12)	0.0439 (12)	0.0043 (9)	0.0032 (10)	−0.0031 (9)
C3	0.0418 (11)	0.0593 (12)	0.0524 (13)	0.0040 (10)	0.0000 (10)	0.0011 (10)
C4	0.0537 (14)	0.0603 (13)	0.0475 (13)	−0.0011 (10)	−0.0073 (11)	−0.0002 (10)
C5	0.0630 (15)	0.0575 (13)	0.0412 (12)	0.0010 (10)	0.0017 (11)	−0.0042 (10)
C6	0.0494 (13)	0.0472 (11)	0.0487 (13)	0.0010 (9)	0.0117 (10)	0.0013 (9)
C7	0.0468 (12)	0.0484 (11)	0.0494 (12)	0.0000 (9)	0.0059 (10)	−0.0025 (9)
C8	0.0401 (11)	0.0430 (11)	0.0551 (13)	−0.0016 (9)	0.0075 (10)	−0.0027 (9)
C9	0.0480 (13)	0.0570 (13)	0.0586 (14)	−0.0036 (10)	0.0080 (11)	0.0085 (11)
C10	0.0406 (12)	0.0562 (13)	0.0706 (15)	−0.0078 (10)	0.0127 (11)	0.0063 (11)
C11	0.0404 (11)	0.0493 (11)	0.0632 (14)	−0.0021 (9)	0.0025 (10)	−0.0071 (11)
C12	0.0519 (13)	0.0645 (14)	0.0516 (13)	−0.0045 (10)	0.0046 (11)	0.0036 (10)
C13	0.0402 (12)	0.0667 (13)	0.0548 (14)	−0.0061 (10)	0.0086 (10)	0.0042 (11)
C14	0.0623 (17)	0.125 (3)	0.079 (2)	−0.0102 (16)	−0.0186 (15)	0.0173 (18)
C15	0.0519 (15)	0.142 (3)	0.0722 (18)	0.0053 (15)	0.0146 (14)	−0.0252 (18)
N1	0.0409 (10)	0.0518 (10)	0.0561 (11)	−0.0028 (8)	0.0057 (8)	0.0023 (8)
O1	0.0402 (9)	0.1206 (15)	0.0637 (11)	0.0052 (9)	0.0009 (8)	−0.0167 (10)
O2	0.0557 (9)	0.0812 (11)	0.0560 (10)	0.0037 (8)	0.0157 (8)	−0.0081 (8)
O3	0.0417 (9)	0.0795 (11)	0.0749 (11)	−0.0074 (7)	−0.0055 (8)	0.0016 (9)

Geometric parameters (Å, º) top

C1—C6	1.407 (3)	C9—H9	0.9300
C1—C2	1.407 (3)	C10—C11	1.393 (3)
C1—C7	1.451 (3)	C10—H10	0.9300
C2—C3	1.373 (3)	C11—O3	1.369 (2)
C2—H2	0.9300	C11—C12	1.386 (3)
C3—O1	1.375 (3)	C12—C13	1.384 (3)
C3—C4	1.393 (3)	C12—H12	0.9300
C4—C5	1.369 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—O3	1.419 (3)
C5—C6	1.381 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—O2	1.356 (2)	C14—H14C	0.9600
C7—N1	1.278 (3)	C15—O1	1.397 (3)
C7—H7	0.9300	C15—H15A	0.9600
C8—C13	1.385 (3)	C15—H15B	0.9600
C8—C9	1.391 (3)	C15—H15C	0.9600
C8—N1	1.419 (2)	O2—H2A	0.8200
C9—C10	1.366 (3)

C6—C1—C2	118.79 (19)	C9—C10—H10	119.9
C6—C1—C7	121.21 (19)	C11—C10—H10	119.9
C2—C1—C7	119.91 (19)	O3—C11—C12	124.9 (2)
C3—C2—C1	120.7 (2)	O3—C11—C10	115.58 (18)
C3—C2—H2	119.6	C12—C11—C10	119.5 (2)
C1—C2—H2	119.6	C13—C12—C11	119.6 (2)
C2—C3—O1	125.3 (2)	C13—C12—H12	120.2
C2—C3—C4	119.3 (2)	C11—C12—H12	120.2
O1—C3—C4	115.40 (19)	C12—C13—C8	121.1 (2)
C5—C4—C3	121.0 (2)	C12—C13—H13	119.5
C5—C4—H4	119.5	C8—C13—H13	119.5
C3—C4—H4	119.5	O3—C14—H14A	109.5
C4—C5—C6	120.4 (2)	O3—C14—H14B	109.5
C4—C5—H5	119.8	H14A—C14—H14B	109.5
C6—C5—H5	119.8	O3—C14—H14C	109.5
O2—C6—C5	118.21 (18)	H14A—C14—H14C	109.5
O2—C6—C1	122.03 (19)	H14B—C14—H14C	109.5
C5—C6—C1	119.75 (19)	O1—C15—H15A	109.5
N1—C7—C1	120.8 (2)	O1—C15—H15B	109.5
N1—C7—H7	119.6	H15A—C15—H15B	109.5
C1—C7—H7	119.6	O1—C15—H15C	109.5
C13—C8—C9	118.6 (2)	H15A—C15—H15C	109.5
C13—C8—N1	123.71 (18)	H15B—C15—H15C	109.5
C9—C8—N1	117.54 (19)	C7—N1—C8	121.78 (19)
C10—C9—C8	120.9 (2)	C3—O1—C15	118.36 (18)
C10—C9—H9	119.6	C6—O2—H2A	109.5
C8—C9—H9	119.6	C11—O3—C14	117.85 (19)
C9—C10—C11	120.29 (19)

C6—C1—C2—C3	−1.5 (3)	N1—C8—C9—C10	176.32 (19)
C7—C1—C2—C3	175.00 (19)	C8—C9—C10—C11	−1.9 (3)
C1—C2—C3—O1	−177.7 (2)	C9—C10—C11—O3	−176.91 (19)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	1.5 (3)
C2—C3—C4—C5	−0.1 (3)	O3—C11—C12—C13	178.0 (2)
O1—C3—C4—C5	178.7 (2)	C10—C11—C12—C13	−0.3 (3)
C3—C4—C5—C6	−0.2 (3)	C11—C12—C13—C8	−0.6 (3)
C4—C5—C6—O2	−179.4 (2)	C9—C8—C13—C12	0.3 (3)
C4—C5—C6—C1	−0.4 (3)	N1—C8—C13—C12	−174.7 (2)
C2—C1—C6—O2	−179.81 (18)	C1—C7—N1—C8	172.99 (18)
C7—C1—C6—O2	3.7 (3)	C13—C8—N1—C7	−36.1 (3)
C2—C1—C6—C5	1.2 (3)	C9—C8—N1—C7	148.9 (2)
C7—C1—C6—C5	−175.24 (19)	C2—C3—O1—C15	−2.2 (4)
C6—C1—C7—N1	−6.4 (3)	C4—C3—O1—C15	179.1 (2)
C2—C1—C7—N1	177.11 (18)	C12—C11—O3—C14	0.9 (3)
C13—C8—C9—C10	1.0 (3)	C10—C11—O3—C14	179.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1—C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.60	3.428 (3)	149
C14—H14A···O1ⁱⁱ	0.96	2.49	3.412 (3)	162
O2—H2A···N1	0.82	1.87	2.590 (2)	146
C5—H5···Cg1ⁱⁱⁱ	0.93	2.80	3.486 (2)	132

Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1; (iii) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₃
M_r	257.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.2658 (8), 14.1553 (11), 6.5893 (17)
β (°)	96.398 (9)
V (Å³)	1322.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.65 × 0.32 × 0.14

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe, 2002)
T_min, T_max	0.991, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	7244, 2585, 1622
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.122, 1.04
No. of reflections	2585
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.19

Computer programs: X-AREA (Stoe, 2002), X-RED32 (Stoe, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1—C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.60	3.428 (3)	149
C14—H14A···O1ⁱⁱ	0.96	2.49	3.412 (3)	162
O2—H2A···N1	0.82	1.87	2.590 (2)	146
C5—H5···Cg1ⁱⁱⁱ	0.93	2.80	3.486 (2)	132

Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1; (iii) x, −y−1/2, z−1/2.

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 No. F279 of the University Research Fund).

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Volume 67| Part 2| February 2011| Pages o343-o344

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