3,5-Dimeth­oxy-2-[(4-propyl­phen­yl)imino­meth­yl]phenol

Şahin, Z.S.; Ağar, A.A.; Erşahin, F.; Işık, Ş.

doi:10.1107/S1600536809007958

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o718

doi:10.1107/S1600536809007958

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3,5-Dimethoxy-2-[(4-propylphenyl)iminomethyl]phenol

Zarife Sibel Şahin,^a ^* Ayşen Alaman Ağar,^b Ferda Erşahin ^b and Şamil Işık ^a

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

(Received 16 January 2009; accepted 4 March 2009; online 11 March 2009)

The title compound, C₁₈H₂₁NO₃, crystallizes in the phenol–imine tautomeric form, with the H atom attached to oxygen rather than on nitrogen. This H atom is involved in a strong intramolecular O—H⋯N hydrogen bond. A C—H⋯π interaction is also present. The dihedral angle between the aromatic rings is 12.23 (7)°.

Related literature

Schiff base compounds can be classified by their photochromic and thermochromic characteristics, see: Cohen et al. (1964 ); Hadjoudis et al. (1987 ); Calligaris et al. (1972 ); Hökelek et al. (2000 ); Dey et al. (2001 ); Ünver et al. (2002 ); Karadayı et al. (2003 ). Bernstein et al. (1995 ) describe the use of graph-set models for the description of hydrogen bonds.

Experimental

Crystal data

C₁₈H₂₁NO₃
M_r = 299.36
Monoclinic, P 2₁ /c
a = 15.1143 (15) Å
b = 7.2587 (5) Å
c = 17.737 (2) Å
β = 123.669 (7)°
V = 1619.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.48 × 0.26 × 0.12 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: none
18964 measured reflections
3353 independent reflections
1337 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.145
S = 0.86
3353 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.87	2.602 (2)	148
C18—H18B⋯Cg2ⁱ	0.96	2.80	3.764 (3)	178
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg2 is the centroid of the C7–C12 ring.

Data collection: X-AREA (Stoe & Cie, 2002 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007958/zl2174sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007958/zl2174Isup2.hkl

checkCIF report

Comment top

Schiff bases have been extensively used as ligands in the field of coordination chemistry (Calligaris et al., 1972). There are two characteristic properties of Schiff bases, viz. photochromism and thermochromism (Cohen et al., 1964). These properties result from proton transfer from the hydroxyl O atom to the imine N atom (Hadjoudis et al., 1987). Schiff bases display two possible tautomeric forms, namely the phenol-imine (Dey et al., 2001; Karadayı et al., 2003) and keto-amine (Hökelek et al., 2000; Ünver et al., 2002) forms.

In the structure of the title compound the N1—C16 bond length of 1.280 (3)Å is typical of a double bond. The dihedral angle between the C1—C6 and C8—C13 benzene rings is 12.23 (7)°. The C1—C16—N1—C7 torsion angle is 178.7 (2)°. Fig. 1 also shows a strong intramolecular hydrogen bond (O2—H2···N1) which can be described with an S(6) graph set motif (Bernstein et al.,1995). The compound also contains one intermolecular C—H···π interaction. Atom C18 in the molecule at (x, y, z) acts as hydrogen-bond donor to the centroid Cg2 of the ring C7—C12 in the molecule at (1 - x, 1/2 + y, 3/2 - z), thus forming a chain running parallel to the [010] direction. The details of C—H···π interaction are given in Table 1.

Related literature top

Schiff base compounds can be classified by their photochromic and thermochromic characteristics, see: Cohen et al. (1964); Hadjoudis et al. (1987); Calligaris et al. (1972); Hökelek et al. (2000); Dey et al. (2001); Ünver et al. (2002); Karadayı et al. (2003). Bernstein et al. (1995) describe the use of graph-set models for the description of hydrogen bonds. Cg2 is the centroid of the C7–C12 ring.

Experimental top

The compound 3,5-dimethoxy-2-[(4-propylphenylimino)methyl]phenol was prepared by refluxing of a mixture of a solution containing 2-hydroxy-4,6-dimethoxy-benzaldehyde (0.0236 g 0.129 mmol) in 20 ml ethanol and a solution containing 4-propylaniline (0.0175 g 0.129 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1 h under reflux. Recrystallization from ethanol gave the pure product. The crystals of 4,6-dimethoxy-2-[(4-propylphenylimino)methyl]phenol suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield % 67; m.p.346–348 K) (Fig. 2).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability. The dashed line represents the O-H···N hydrogen bond.
	Fig. 2. Synthesis of the title compound.

3,5-Dimethoxy-2-[(4-propylphenyl)iminomethyl]phenol top

Crystal data top

C₁₈H₂₁NO₃	F(000) = 640
M_r = 299.36	D_x = 1.228 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10898 reflections
a = 15.1143 (15) Å	θ = 1.4–28.0°
b = 7.2587 (5) Å	µ = 0.08 mm⁻¹
c = 17.737 (2) Å	T = 296 K
β = 123.669 (7)°	Prism, yellow
V = 1619.5 (3) Å³	0.48 × 0.26 × 0.12 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	1337 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.075
Graphite monochromator	θ_max = 26.5°, θ_min = 1.6°
Detector resolution: 6.67 pixels mm^-1	h = −18→18
ω scans	k = −8→9
18964 measured reflections	l = −22→22
3353 independent 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.0666P)²] where P = (F_o² + 2F_c²)/3
3353 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₂₁NO₃	V = 1619.5 (3) Å³
M_r = 299.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.1143 (15) Å	µ = 0.08 mm⁻¹
b = 7.2587 (5) Å	T = 296 K
c = 17.737 (2) Å	0.48 × 0.26 × 0.12 mm
β = 123.669 (7)°

Data collection top

Stoe IPDS-II diffractometer	1337 reflections with I > 2σ(I)
18964 measured reflections	R_int = 0.075
3353 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 0.86	Δρ_max = 0.14 e Å⁻³
3353 reflections	Δρ_min = −0.21 e Å⁻³
200 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	0.53442 (17)	0.1004 (3)	0.80353 (15)	0.0667 (6)
C2	0.57933 (17)	0.1123 (3)	0.75252 (15)	0.0672 (6)
C3	0.68738 (17)	0.1079 (3)	0.79200 (16)	0.0722 (7)
H3	0.7155	0.1170	0.7569	0.087*
C4	0.75352 (18)	0.0896 (3)	0.88549 (17)	0.0730 (7)
C5	0.71280 (19)	0.0762 (4)	0.93799 (17)	0.0825 (8)
H5	0.7584	0.0629	1.0004	0.099*
C6	0.60502 (18)	0.0825 (3)	0.89829 (16)	0.0732 (7)
C7	0.26549 (18)	0.0884 (3)	0.76044 (16)	0.0678 (6)
C8	0.1924 (2)	0.1356 (4)	0.67118 (18)	0.0873 (8)
H8	0.2159	0.1722	0.6348	0.105*
C9	0.0850 (2)	0.1289 (4)	0.63550 (19)	0.0919 (8)
H9	0.0375	0.1597	0.5749	0.110*
C10	0.0452 (2)	0.0787 (4)	0.6858 (2)	0.0817 (7)
C11	0.1189 (2)	0.0343 (4)	0.7747 (2)	0.0931 (9)
H11	0.0953	0.0002	0.8112	0.112*
C12	0.2272 (2)	0.0384 (4)	0.81199 (18)	0.0870 (8)
H12	0.2745	0.0069	0.8725	0.104*
C16	0.42105 (17)	0.1008 (3)	0.76044 (16)	0.0719 (7)
H16	0.3775	0.1081	0.6976	0.086*
C18	0.90908 (19)	0.1115 (4)	0.8815 (2)	0.1004 (9)
H18A	0.9850	0.1025	0.9219	0.151*
H18B	0.8904	0.2318	0.8546	0.151*
H18C	0.8840	0.0200	0.8349	0.151*
C17	0.5443 (2)	0.1229 (5)	0.60388 (16)	0.0988 (9)
H17A	0.4853	0.1357	0.5421	0.148*
H17B	0.5792	0.0074	0.6113	0.148*
H17C	0.5936	0.2219	0.6191	0.148*
C13	−0.0731 (2)	0.0740 (5)	0.6453 (2)	0.1140 (11)
H13A	−0.0832	0.0528	0.6941	0.137*
H13B	−0.1018	0.1950	0.6205	0.137*
C14	−0.1353 (2)	−0.0597 (5)	0.5758 (2)	0.1255 (12)
H14A	−0.1062	−0.1811	0.5996	0.151*
H14B	−0.1278	−0.0367	0.5257	0.151*
C15	−0.2534 (2)	−0.0615 (5)	0.5394 (2)	0.1338 (14)
H15A	−0.2886	−0.1549	0.4937	0.201*
H15B	−0.2838	0.0566	0.5136	0.201*
H15C	−0.2621	−0.0872	0.5880	0.201*
N1	0.37759 (14)	0.0914 (3)	0.80506 (13)	0.0738 (6)
O1	0.86157 (12)	0.0821 (3)	0.93083 (11)	0.0921 (6)
O2	0.56789 (13)	0.0725 (3)	0.95188 (11)	0.0995 (7)
H2	0.5027	0.0758	0.9205	0.149*
O3	0.50721 (11)	0.1284 (3)	0.66174 (10)	0.0869 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0666 (14)	0.0706 (17)	0.0586 (14)	−0.0048 (12)	0.0320 (13)	−0.0038 (13)
C2	0.0695 (15)	0.0707 (17)	0.0538 (14)	−0.0022 (12)	0.0293 (13)	−0.0031 (13)
C3	0.0699 (15)	0.0791 (18)	0.0677 (16)	−0.0023 (13)	0.0382 (13)	−0.0020 (15)
C4	0.0604 (14)	0.0728 (18)	0.0689 (16)	−0.0079 (12)	0.0254 (13)	−0.0030 (14)
C5	0.0741 (16)	0.106 (2)	0.0550 (14)	−0.0098 (15)	0.0280 (13)	−0.0006 (15)
C6	0.0744 (16)	0.0859 (19)	0.0553 (15)	−0.0108 (13)	0.0334 (14)	−0.0040 (14)
C7	0.0701 (15)	0.0712 (17)	0.0626 (15)	0.0008 (13)	0.0370 (14)	0.0005 (13)
C8	0.0779 (17)	0.100 (2)	0.0752 (18)	−0.0001 (15)	0.0368 (15)	0.0181 (16)
C9	0.0726 (17)	0.103 (2)	0.0811 (19)	0.0046 (15)	0.0309 (15)	0.0133 (17)
C10	0.0770 (16)	0.0770 (19)	0.094 (2)	0.0042 (14)	0.0491 (17)	−0.0086 (16)
C11	0.092 (2)	0.112 (2)	0.094 (2)	0.0066 (17)	0.0632 (19)	−0.0021 (19)
C12	0.0814 (18)	0.111 (2)	0.0739 (17)	0.0118 (15)	0.0463 (16)	0.0044 (15)
C16	0.0728 (15)	0.0767 (18)	0.0590 (14)	0.0011 (13)	0.0322 (13)	−0.0028 (14)
C18	0.0740 (16)	0.115 (2)	0.109 (2)	−0.0058 (16)	0.0486 (17)	0.0204 (19)
C17	0.0904 (17)	0.151 (3)	0.0602 (16)	0.0001 (18)	0.0451 (15)	−0.0106 (18)
C13	0.0812 (18)	0.124 (3)	0.131 (3)	0.0047 (18)	0.0549 (19)	−0.025 (2)
C14	0.0813 (19)	0.153 (3)	0.137 (3)	−0.007 (2)	0.057 (2)	−0.023 (3)
C15	0.0733 (19)	0.149 (3)	0.162 (3)	−0.0030 (19)	0.054 (2)	0.006 (3)
N1	0.0709 (12)	0.0871 (16)	0.0628 (12)	−0.0019 (11)	0.0367 (11)	−0.0005 (11)
O1	0.0646 (10)	0.1177 (16)	0.0783 (12)	−0.0085 (10)	0.0298 (10)	0.0050 (11)
O2	0.0793 (11)	0.156 (2)	0.0590 (10)	−0.0110 (13)	0.0359 (9)	0.0003 (12)
O3	0.0715 (10)	0.1344 (16)	0.0519 (10)	0.0047 (10)	0.0324 (9)	0.0013 (11)

Geometric parameters (Å, º) top

C1—C2	1.403 (3)	C11—H11	0.9300
C1—C6	1.411 (3)	C12—H12	0.9300
C1—C16	1.438 (3)	C16—N1	1.280 (3)
C2—O3	1.360 (2)	C16—H16	0.9300
C2—C3	1.375 (3)	C18—O1	1.422 (3)
C3—C4	1.389 (3)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—O1	1.364 (3)	C18—H18C	0.9600
C4—C5	1.375 (3)	C17—O3	1.417 (2)
C5—C6	1.371 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—O2	1.347 (3)	C17—H17C	0.9600
C7—C12	1.374 (3)	C13—C14	1.435 (4)
C7—C8	1.380 (3)	C13—H13A	0.9700
C7—N1	1.418 (3)	C13—H13B	0.9700
C8—C9	1.379 (3)	C14—C15	1.525 (3)
C8—H8	0.9300	C14—H14A	0.9700
C9—C10	1.373 (3)	C14—H14B	0.9700
C9—H9	0.9300	C15—H15A	0.9600
C10—C11	1.373 (4)	C15—H15B	0.9600
C10—C13	1.514 (3)	C15—H15C	0.9600
C11—C12	1.385 (3)	O2—H2	0.8200

C2—C1—C6	117.2 (2)	N1—C16—H16	118.7
C2—C1—C16	121.1 (2)	C1—C16—H16	118.7
C6—C1—C16	121.6 (2)	O1—C18—H18A	109.5
O3—C2—C3	123.5 (2)	O1—C18—H18B	109.5
O3—C2—C1	114.34 (19)	H18A—C18—H18B	109.5
C3—C2—C1	122.2 (2)	O1—C18—H18C	109.5
C2—C3—C4	118.4 (2)	H18A—C18—H18C	109.5
C2—C3—H3	120.8	H18B—C18—H18C	109.5
C4—C3—H3	120.8	O3—C17—H17A	109.5
O1—C4—C5	115.9 (2)	O3—C17—H17B	109.5
O1—C4—C3	122.8 (2)	H17A—C17—H17B	109.5
C5—C4—C3	121.3 (2)	O3—C17—H17C	109.5
C6—C5—C4	120.0 (2)	H17A—C17—H17C	109.5
C6—C5—H5	120.0	H17B—C17—H17C	109.5
C4—C5—H5	120.0	C14—C13—C10	117.5 (3)
O2—C6—C5	118.5 (2)	C14—C13—H13A	107.9
O2—C6—C1	120.6 (2)	C10—C13—H13A	107.9
C5—C6—C1	120.9 (2)	C14—C13—H13B	107.9
C12—C7—C8	117.7 (2)	C10—C13—H13B	107.9
C12—C7—N1	116.5 (2)	H13A—C13—H13B	107.2
C8—C7—N1	125.8 (2)	C13—C14—C15	115.1 (3)
C9—C8—C7	120.5 (2)	C13—C14—H14A	108.5
C9—C8—H8	119.8	C15—C14—H14A	108.5
C7—C8—H8	119.8	C13—C14—H14B	108.5
C10—C9—C8	122.7 (3)	C15—C14—H14B	108.5
C10—C9—H9	118.7	H14A—C14—H14B	107.5
C8—C9—H9	118.7	C14—C15—H15A	109.5
C9—C10—C11	116.1 (2)	C14—C15—H15B	109.5
C9—C10—C13	121.7 (3)	H15A—C15—H15B	109.5
C11—C10—C13	122.2 (3)	C14—C15—H15C	109.5
C10—C11—C12	122.3 (3)	H15A—C15—H15C	109.5
C10—C11—H11	118.8	H15B—C15—H15C	109.5
C12—C11—H11	118.8	C16—N1—C7	121.3 (2)
C7—C12—C11	120.7 (3)	C4—O1—C18	118.6 (2)
C7—C12—H12	119.7	C6—O2—H2	109.5
C11—C12—H12	119.7	C2—O3—C17	118.41 (18)
N1—C16—C1	122.7 (2)

C6—C1—C2—O3	179.7 (2)	C8—C9—C10—C11	−0.2 (4)
C16—C1—C2—O3	1.6 (3)	C8—C9—C10—C13	179.5 (3)
C6—C1—C2—C3	−0.3 (4)	C9—C10—C11—C12	−0.4 (4)
C16—C1—C2—C3	−178.5 (2)	C13—C10—C11—C12	180.0 (3)
O3—C2—C3—C4	−179.5 (2)	C8—C7—C12—C11	0.6 (4)
C1—C2—C3—C4	0.5 (4)	N1—C7—C12—C11	179.0 (2)
C2—C3—C4—O1	179.3 (2)	C10—C11—C12—C7	0.2 (4)
C2—C3—C4—C5	−0.1 (4)	C2—C1—C16—N1	−179.5 (2)
O1—C4—C5—C6	180.0 (2)	C6—C1—C16—N1	2.5 (4)
C3—C4—C5—C6	−0.6 (4)	C9—C10—C13—C14	66.0 (4)
C4—C5—C6—O2	−178.8 (2)	C11—C10—C13—C14	−114.4 (4)
C4—C5—C6—C1	0.8 (4)	C10—C13—C14—C15	178.4 (3)
C2—C1—C6—O2	179.2 (2)	C1—C16—N1—C7	−178.7 (2)
C16—C1—C6—O2	−2.7 (4)	C12—C7—N1—C16	166.3 (2)
C2—C1—C6—C5	−0.3 (4)	C8—C7—N1—C16	−15.5 (4)
C16—C1—C6—C5	177.8 (2)	C5—C4—O1—C18	−174.5 (2)
C12—C7—C8—C9	−1.1 (4)	C3—C4—O1—C18	6.1 (4)
N1—C7—C8—C9	−179.3 (2)	C3—C2—O3—C17	6.2 (4)
C7—C8—C9—C10	0.9 (4)	C1—C2—O3—C17	−173.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.87	2.602 (2)	148
C18—H18B···Cg2ⁱ	0.96	2.80	3.764 (3)	178

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁NO₃
M_r	299.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.1143 (15), 7.2587 (5), 17.737 (2)
β (°)	123.669 (7)
V (Å³)	1619.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.26 × 0.12

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18964, 3353, 1337
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.145, 0.86
No. of reflections	3353
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.21

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.87	2.602 (2)	148.3
C18—H18B···Cg2ⁱ	0.96	2.80	3.764 (3)	177.6

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences of Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant No. F279 of the University Research Grant of Ondokuz Mayıs University).

References

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