2-((E)-{[4-(Hy­droxy­meth­yl)phen­yl]imino}­meth­yl)phenol

Mohamed, S.K.; Abdelhamid, A.A.; Akkurt, M.; Fanwick, P.E.; Maharramov, A.M.

doi:10.1107/S1600536812019368

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1618

doi:10.1107/S1600536812019368

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2-((E)-{[4-(Hydroxymethyl)phenyl]imino}methyl)phenol

Shaaban K. Mohamed,^a Antar A. Abdelhamid,^a Mehmet Akkurt,^b ^* Phillip E. Fanwick ^c and A. M. Maharramov ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, Purdue University, W. Lafayette, IN 47907, USA, and ^dDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 25 April 2012; accepted 30 April 2012; online 5 May 2012)

The title compound, C₁₄H₁₃NO₂, adopts the enol–imine tautomeric form, with an intramolecular O—H⋯N hydrogen bond which generates an S(6) ring motif. The dihedral angle between the aromatic rings is 7.85 (7)°. The crystal structure is stabilized by O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, forming a two-dimensional array that stacks along the a axis. In addition, a C—H⋯π interaction contributes to the stabilization of the crystal packing.

Related literature

For background to Schiff base compounds, see: Elena et al. (2000 ); Mohamed et al. (2006 ); Rajavel et al. (2008 ); Uğraş et al. (2006 ); Wadher et al. (2009 ). For similar structures, see: Deveci et al. (2008 ); Karadayı et al. (2003 ); Koşar et al. (2010 ); Ünver et al. (2002 ). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Monoclinic, P 2₁ /c
a = 19.8172 (14) Å
b = 4.7217 (1) Å
c = 12.3106 (2) Å
β = 104.005 (7)°
V = 1117.67 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.73 mm⁻¹
T = 150 K
0.25 × 0.20 × 0.08 mm

Data collection

Rigaku RAPID II diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001 ) T_min = 0.838, T_max = 0.944
10711 measured reflections
1958 independent reflections
1641 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.14
1958 reflections
163 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1ⁱ	0.94 (3)	1.79 (2)	2.7235 (14)	172 (2)
O2—H2⋯N1	0.93 (2)	1.74 (2)	2.5990 (15)	151.7 (19)
C7—H7⋯O1ⁱⁱ	0.95	2.57	3.4288 (16)	150
C8—H8⋯O2ⁱⁱⁱ	0.95	2.59	3.4492 (16)	151
C1—H1B⋯Cg1^iv	0.99	2.56	3.5050 (15)	160
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x, y-1, z.

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019368/tk5090sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019368/tk5090Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019368/tk5090Isup3.cml

checkCIF report

Comment top

Schiff base compounds are important class of materials due to their flexibility, structural similarities with natural biological substances and also due to presence of imine (–N=CH–) which relates to the mechanism of transformation and racemisation reactions in biological system (Rajavel et al., 2008). Schiff bases-bimolecular condensation products of amnio alcohols with aldehydes represent valuable intermediates in organic synthesis with various applications (Uğraş et al., 2006). Schiff bases resulted from aromatic aldehydes ortho-substituted with a hydroxyl group initially aroused interest due to the several donor atoms in their structures which give them an advantage to form a water soluble transition metal complexes (Wadher et al., 2009). This advantage raises potential applications in water treatment (Elena et al., 2000). They could also act as valuable ligands whose biological activity has been shown to increase on complexation (Mohamed et al., 2006).

As seen in Fig. 1, the title compound shows the enol-imine tautomeric form, which has an intramolecular O— H···N hydrogen bond forming an S(6) ring motif (Bernstein et al., 1995). The C14—O2 single bond [1.3525 (17) Å] and the C8═N1 double bond [1.2829 (17) Å] verify the enol-imine form. These distances and the values of the other geometric parameters are in the normal range and are comparable with those of other similar compounds reported previously (Koşar, et al., 2010; Deveci et al., 2008; Ünver et al., 2002; Karadayı et al., 2003). The N1—C8—C9—C14 torsion angle is 1.8 (2)°. Therefore, the N1/C8/C9/C14/O2/H2 S(6) ring is essentially coplanar with the C9–C14 benzene ring to which it is bonded.

In the crystal, molecules are linked by O—H···O and weak C—H···O hydrogen bonds, forming a two dimensional array that stacks along the a axis Fig. 2 and Table 1. The crystal packing is further stabilized by C—H···π interactions, Table 1.

Related literature top

For background to Schiff base compounds, see: Elena et al. (2000); Mohamed et al. (2006); Rajavel et al. (2008); Uğraş et al. (2006); Wadher et al. (2009). For similar structures, see: Deveci et al. (2008); Karadayı et al. (2003); Koşar et al. (2010); Ünver et al. (2002). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized as a secondary product from a three component reaction of cyclohexane-1,3-dione (1 mmol), (4-aminophenyl)methanol (1 mmol), and salicylaldehde (1 mmol). The reaction mixture was refluxed in ethanol at 351 K for four hours then left at room temperature for two days. The resulting solid product was filtered of, dried and recrystallized from ethanol. (43% yield, M.pt: 403 K). Crystals suitable for X-ray diffraction were grown in a diluted ethanol solution at room temperature by the slow evaporation method.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: CrystalClear (Rigaku/MSC, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. The crystal packing and hydrogen bonding of (I), viewed along the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity.

2-((E)-{[4-(Hydroxymethyl)phenyl]imino}methyl)phenol top

Crystal data top

C₁₄H₁₃NO₂	F(000) = 480
M_r = 227.25	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 11657 reflections
a = 19.8172 (14) Å	θ = 2–66°
b = 4.7217 (1) Å	µ = 0.73 mm⁻¹
c = 12.3106 (2) Å	T = 150 K
β = 104.005 (7)°	Plate, yellow
V = 1117.67 (9) Å³	0.25 × 0.20 × 0.08 mm
Z = 4

Data collection top

Rigaku RAPID II diffractometer	1641 reflections with I > 2σ(I)
Confocal optics monochromator	R_int = 0.030
ω scans	θ_max = 66.6°, θ_min = 4.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	h = −23→23
T_min = 0.838, T_max = 0.944	k = −5→5
10711 measured reflections	l = −11→14
1958 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0585P)² + 0.170P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
1958 reflections	Δρ_max = 0.23 e Å⁻³
163 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0077 (8)

Crystal data top

C₁₄H₁₃NO₂	V = 1117.67 (9) Å³
M_r = 227.25	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 19.8172 (14) Å	µ = 0.73 mm⁻¹
b = 4.7217 (1) Å	T = 150 K
c = 12.3106 (2) Å	0.25 × 0.20 × 0.08 mm
β = 104.005 (7)°

Data collection top

Rigaku RAPID II diffractometer	1958 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	1641 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.944	R_int = 0.030
10711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.23 e Å⁻³
1958 reflections	Δρ_min = −0.18 e Å⁻³
163 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.46733 (5)	0.1618 (2)	0.25819 (8)	0.0330 (3)
O2	0.19567 (6)	1.2380 (2)	0.56950 (8)	0.0408 (4)
N1	0.24780 (5)	0.9636 (2)	0.42590 (9)	0.0258 (3)
C1	0.44786 (7)	0.1429 (3)	0.36158 (11)	0.0285 (4)
C2	0.39457 (6)	0.3581 (3)	0.37420 (11)	0.0252 (4)
C3	0.34633 (7)	0.4685 (3)	0.28219 (11)	0.0278 (4)
C4	0.29742 (7)	0.6676 (3)	0.29556 (11)	0.0279 (4)
C5	0.29508 (6)	0.7592 (3)	0.40265 (11)	0.0245 (4)
C6	0.34194 (7)	0.6431 (3)	0.49448 (11)	0.0279 (4)
C7	0.39100 (7)	0.4468 (3)	0.48021 (11)	0.0287 (4)
C8	0.20820 (6)	1.1083 (3)	0.34759 (11)	0.0257 (4)
C9	0.15921 (6)	1.3145 (3)	0.37087 (11)	0.0259 (4)
C10	0.11604 (6)	1.4634 (3)	0.28242 (11)	0.0296 (4)
C11	0.06849 (7)	1.6600 (3)	0.30125 (13)	0.0340 (4)
C12	0.06377 (7)	1.7098 (3)	0.41032 (13)	0.0371 (5)
C13	0.10585 (7)	1.5687 (3)	0.49924 (12)	0.0375 (5)
C14	0.15422 (7)	1.3713 (3)	0.48079 (11)	0.0299 (4)
H1	0.4926 (14)	0.330 (5)	0.259 (2)	0.099 (8)*
H1A	0.48990	0.16730	0.42350	0.0340*
H1B	0.42910	−0.04890	0.36840	0.0340*
H2	0.2230 (10)	1.115 (5)	0.5393 (17)	0.071 (6)*
H3	0.34690	0.40630	0.20900	0.0330*
H4	0.26540	0.74190	0.23170	0.0330*
H6	0.34030	0.69910	0.56790	0.0340*
H7	0.42280	0.37140	0.54410	0.0340*
H8	0.21100	1.07970	0.27240	0.0310*
H10	0.11950	1.42860	0.20800	0.0360*
H11	0.03950	1.75950	0.24050	0.0410*
H12	0.03090	1.84360	0.42380	0.0440*
H13	0.10190	1.60590	0.57330	0.0450*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0382 (6)	0.0280 (5)	0.0374 (6)	0.0013 (4)	0.0182 (4)	0.0000 (4)
O2	0.0522 (7)	0.0451 (7)	0.0276 (6)	0.0127 (5)	0.0147 (5)	0.0002 (5)
N1	0.0276 (6)	0.0231 (6)	0.0285 (6)	−0.0012 (4)	0.0104 (5)	−0.0012 (4)
C1	0.0317 (7)	0.0239 (7)	0.0317 (7)	−0.0005 (5)	0.0113 (6)	0.0021 (5)
C2	0.0270 (7)	0.0198 (6)	0.0305 (7)	−0.0041 (5)	0.0102 (6)	0.0012 (5)
C3	0.0331 (7)	0.0266 (7)	0.0255 (7)	−0.0008 (5)	0.0105 (6)	−0.0023 (5)
C4	0.0301 (7)	0.0283 (7)	0.0248 (7)	0.0021 (5)	0.0059 (6)	0.0010 (5)
C5	0.0272 (7)	0.0209 (6)	0.0275 (7)	−0.0034 (5)	0.0110 (6)	−0.0013 (5)
C6	0.0354 (7)	0.0264 (7)	0.0236 (7)	−0.0019 (5)	0.0102 (6)	−0.0013 (5)
C7	0.0319 (7)	0.0256 (7)	0.0277 (7)	−0.0006 (6)	0.0054 (6)	0.0025 (5)
C8	0.0289 (7)	0.0235 (7)	0.0263 (7)	−0.0042 (5)	0.0101 (6)	−0.0025 (5)
C9	0.0265 (7)	0.0212 (6)	0.0323 (7)	−0.0041 (5)	0.0116 (6)	−0.0025 (5)
C10	0.0303 (7)	0.0279 (7)	0.0315 (7)	−0.0024 (5)	0.0090 (6)	−0.0015 (6)
C11	0.0291 (7)	0.0275 (7)	0.0451 (9)	0.0001 (6)	0.0085 (6)	0.0008 (6)
C12	0.0326 (8)	0.0302 (8)	0.0528 (10)	0.0022 (6)	0.0189 (7)	−0.0049 (7)
C13	0.0445 (8)	0.0356 (8)	0.0383 (8)	0.0005 (7)	0.0213 (7)	−0.0063 (7)
C14	0.0329 (7)	0.0283 (7)	0.0311 (7)	−0.0018 (5)	0.0130 (6)	−0.0010 (6)

Geometric parameters (Å, º) top

O1—C1	1.4193 (17)	C10—C11	1.382 (2)
O2—C14	1.3525 (17)	C11—C12	1.388 (2)
O1—H1	0.94 (3)	C12—C13	1.377 (2)
O2—H2	0.93 (2)	C13—C14	1.395 (2)
N1—C5	1.4216 (17)	C1—H1A	0.9900
N1—C8	1.2829 (17)	C1—H1B	0.9900
C1—C2	1.5004 (19)	C3—H3	0.9500
C2—C7	1.3886 (19)	C4—H4	0.9500
C2—C3	1.3945 (19)	C6—H6	0.9500
C3—C4	1.388 (2)	C7—H7	0.9500
C4—C5	1.3989 (19)	C8—H8	0.9500
C5—C6	1.3902 (19)	C10—H10	0.9500
C6—C7	1.385 (2)	C11—H11	0.9500
C8—C9	1.4516 (19)	C12—H12	0.9500
C9—C14	1.4063 (19)	C13—H13	0.9500
C9—C10	1.4003 (19)

C1—O1—H1	107.7 (15)	O2—C14—C13	119.12 (12)
C14—O2—H2	105.4 (13)	O1—C1—H1A	109.00
C5—N1—C8	121.56 (11)	O1—C1—H1B	109.00
O1—C1—C2	113.65 (11)	C2—C1—H1A	109.00
C1—C2—C7	119.92 (12)	C2—C1—H1B	109.00
C3—C2—C7	118.02 (12)	H1A—C1—H1B	108.00
C1—C2—C3	122.03 (12)	C2—C3—H3	119.00
C2—C3—C4	121.19 (12)	C4—C3—H3	119.00
C3—C4—C5	120.29 (12)	C3—C4—H4	120.00
N1—C5—C4	124.99 (12)	C5—C4—H4	120.00
C4—C5—C6	118.46 (12)	C5—C6—H6	120.00
N1—C5—C6	116.56 (12)	C7—C6—H6	120.00
C5—C6—C7	120.80 (12)	C2—C7—H7	119.00
C2—C7—C6	121.20 (12)	C6—C7—H7	119.00
N1—C8—C9	121.70 (12)	N1—C8—H8	119.00
C10—C9—C14	118.72 (12)	C9—C8—H8	119.00
C8—C9—C10	119.68 (12)	C9—C10—H10	119.00
C8—C9—C14	121.60 (12)	C11—C10—H10	119.00
C9—C10—C11	121.33 (13)	C10—C11—H11	120.00
C10—C11—C12	118.97 (13)	C12—C11—H11	121.00
C11—C12—C13	121.15 (13)	C11—C12—H12	119.00
C12—C13—C14	120.12 (13)	C13—C12—H12	119.00
C9—C14—C13	119.70 (13)	C12—C13—H13	120.00
O2—C14—C9	121.19 (12)	C14—C13—H13	120.00

C5—N1—C8—C9	179.17 (12)	C5—C6—C7—C2	−0.6 (2)
C8—N1—C5—C4	−8.8 (2)	N1—C8—C9—C10	−178.71 (12)
C8—N1—C5—C6	171.49 (12)	N1—C8—C9—C14	1.8 (2)
O1—C1—C2—C7	−153.49 (12)	C8—C9—C10—C11	179.61 (13)
O1—C1—C2—C3	28.42 (18)	C14—C9—C10—C11	−0.9 (2)
C3—C2—C7—C6	−1.2 (2)	C8—C9—C14—O2	0.9 (2)
C1—C2—C3—C4	−179.98 (14)	C8—C9—C14—C13	−179.25 (13)
C1—C2—C7—C6	−179.38 (13)	C10—C9—C14—O2	−178.60 (12)
C7—C2—C3—C4	1.9 (2)	C10—C9—C14—C13	1.3 (2)
C2—C3—C4—C5	−0.8 (2)	C9—C10—C11—C12	0.0 (2)
C3—C4—C5—C6	−1.0 (2)	C10—C11—C12—C13	0.5 (2)
C3—C4—C5—N1	179.32 (13)	C11—C12—C13—C14	−0.1 (2)
C4—C5—C6—C7	1.7 (2)	C12—C13—C14—O2	179.11 (13)
N1—C5—C6—C7	−178.61 (12)	C12—C13—C14—C9	−0.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.94 (3)	1.79 (2)	2.7235 (14)	172 (2)
O2—H2···N1	0.93 (2)	1.74 (2)	2.5990 (15)	151.7 (19)
C7—H7···O1ⁱⁱ	0.95	2.57	3.4288 (16)	150
C8—H8···O2ⁱⁱⁱ	0.95	2.59	3.4492 (16)	151
C1—H1B···Cg1^iv	0.99	2.56	3.5050 (15)	160

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+5/2, z−1/2; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	19.8172 (14), 4.7217 (1), 12.3106 (2)
β (°)	104.005 (7)
V (Å³)	1117.67 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.25 × 0.20 × 0.08

Data collection
Diffractometer	Rigaku RAPID II diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2001)
T_min, T_max	0.838, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	10711, 1958, 1641
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.14
No. of reflections	1958
No. of parameters	163
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: CrystalClear (Rigaku/MSC, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.94 (3)	1.79 (2)	2.7235 (14)	172 (2)
O2—H2···N1	0.93 (2)	1.74 (2)	2.5990 (15)	151.7 (19)
C7—H7···O1ⁱⁱ	0.95	2.57	3.4288 (16)	150
C8—H8···O2ⁱⁱⁱ	0.95	2.59	3.4492 (16)	151
C1—H1B···Cg1^iv	0.99	2.56	3.5050 (15)	160

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+5/2, z−1/2; (iv) x, y−1, z.

Acknowledgements

The authors are grateful to the Higher Education Ministry of Egypt for financial support of this project. Manchester Metropolitan University and Purdue University are also acknowledged for the data collection and support of this study.

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