(E)-2-[(4-Chloro­phen­yl)imino­meth­yl]-4-(trifluoro­meth­oxy)phenol

Tüfekçi, M.; Bingöl Alpaslan, Y.; Macit, M.; Erdönmez, A.

doi:10.1107/S1600536809040690

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2704

https://doi.org/10.1107/S1600536809040690

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(E)-2-[(4-Chlorophenyl)iminomethyl]-4-(trifluoromethoxy)phenol

Marife Tüfekçi,^a Yelda Bingöl Alpaslan,^a Mustafa Macit ^b and Ahmet Erdönmez ^a ^*

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

(Received 5 October 2009; accepted 6 October 2009; online 10 October 2009)

The title compound, C₁₄H₉ClF₃NO₂, crystallizes in a phenol–imine tautomeric form, with a strong intramolecular O—H⋯N hydrogen bond. The dihedral angle between the two benzene rings is 47.62 (9)°. In the crystal, molecules are linked into chains along the c axis by C—H⋯O hydrogen bonds, and weak C—H⋯π interactions involving both benzene rings are also observed.

Related literature

For general background to Schiff bases, see: Calligaris et al. (1972 ); Cohen et al. (1964 ); Hadjoudis et al. (1987 ); Karadayı et al. (2003 ); Hökelek et al.(2000 ); Dey et al. (2001 ); Ünver et al. (2002 ). For a related structure, see: Gül et al. (2007 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₉ClF₃NO₂
M_r = 315.67
Monoclinic, P 2₁ /c
a = 29.612 (5) Å
b = 7.195 (5) Å
c = 6.375 (5) Å
β = 96.012 (5)°
V = 1350.8 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.72 × 0.44 × 0.10 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.844, T_max = 0.966
11226 measured reflections
2579 independent reflections
1539 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.201
S = 1.04
2579 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.33 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	1.88	2.604 (4)	147
C14—H14⋯O1ⁱ	0.93	2.53	3.396 (5)	155
C2—H2⋯Cg1ⁱⁱ	0.93	2.77	3.496 (4)	135
C5—H5⋯Cg1ⁱⁱⁱ	0.93	2.98	3.713 (4)	136
C10—H10⋯Cg2^iv	0.93	2.94	3.644 (4)	133
C13—H13⋯Cg2^v	0.93	2.88	3.597 (4)	135
Symmetry codes: (i) x, y, z-1; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

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: https://doi.org/10.1107/S1600536809040690/ci2934sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040690/ci2934Isup2.hkl

checkCIF report

Comment top

Schiff bases have been extensively used as ligands in the field of coordination chemistry (Calligaris et al., 1972). Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Cohen et al., 1964). These properties result from a 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) forms. Our X-ray analysis shows that the title compound, (I), exists in the phenol-imine form (Fig. 1).

The C8═N1 [1.282 (4) Å] and C6—O1 [1.343 (4) Å] bond lenghts confirm the phenol-imine form of (I), and these distances are similar to those reported in the literature [1.280 (2) Å and 1.350 (3) Å; Gül et al., 2007]. The molecule is not planar and the dihedral angle between the C1-C6 and C9-C14 rings is 47.62 (9)°. A strong intramolecular O1—H1···N1 hydrogen bond which forms an S(6) graph set motif (Bernstein et al., 1995) is observed.

The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds (Table 1). In addition, C2—H2···Cg1ⁱ, C5—H5···Cg1ⁱⁱ, C10—H10···Cg2ⁱⁱⁱ and C13—H13···Cg2^iv (Cg1 and Cg2 are centroids of the C1-C6 and C9-C14 rings, respectively) interactions (Fig.2 and Table 1) are observed.

Related literature top

For general background to Schiff bases, see: Calligaris et al. (1972); Cohen et al. (1964); Hadjoudis et al. (1987); Karadayı et al. (2003); Hökelek et al.(2000); Dey et al. (2001); Ünver et al. (2002). For a related structure, see: Gül et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 and Cg2 are the centroids

of the C1–C6 and C9–C14 rings, respectively.

Experimental top

2-[(4-Chlorophenyl)iminomethyl]-4-trifluoromethoxyphenol was prepared by refluxing a mixture of a solution containing 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (10 mg, 4.85× 10^-2 mmol) in ethanol (20 ml) and a solution containing 4-chloroaniline (10 mg, 4.85× 10^-2 mmol) in ethanol (20 ml). The reaction mixture was stirred for 1 hour under reflux. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 44 %; m.p. 376-377 K).

Structure description top

For general background to Schiff bases, see: Calligaris et al. (1972); Cohen et al. (1964); Hadjoudis et al. (1987); Karadayı et al. (2003); Hökelek et al.(2000); Dey et al. (2001); Ünver et al. (2002). For a related structure, see: Gül et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 and Cg2 are the centroids

of the C1–C6 and C9–C14 rings, respectively.

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 (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates a hydrogen bond.
	Fig. 2. A packing diagram for (I). H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

(E)-2-[(4-Chlorophenyl)iminomethyl]-4-(trifluoromethoxy)phenol top

Crystal data top

C₁₄H₉ClF₃NO₂	F(000) = 640
M_r = 315.67	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 13303 reflections
a = 29.612 (5) Å	θ = 2.1–26.7°
b = 7.195 (5) Å	µ = 0.32 mm⁻¹
c = 6.375 (5) Å	T = 296 K
β = 96.012 (5)°	Plate, light brown
V = 1350.8 (14) Å³	0.72 × 0.44 × 0.10 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	2579 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.8°
ω scans	h = −36→32
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
T_min = 0.844, T_max = 0.966	l = −7→7
11226 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.201	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1139P)²] where P = (F_o² + 2F_c²)/3
2579 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₄H₉ClF₃NO₂	V = 1350.8 (14) Å³
M_r = 315.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 29.612 (5) Å	µ = 0.32 mm⁻¹
b = 7.195 (5) Å	T = 296 K
c = 6.375 (5) Å	0.72 × 0.44 × 0.10 mm
β = 96.012 (5)°

Data collection top

Stoe IPDS-II diffractometer	2579 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1539 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.966	R_int = 0.059
11226 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.201	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
2579 reflections	Δρ_min = −0.33 e Å⁻³
190 parameters

Special details top

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.

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 > 2sigma(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	0.79069 (11)	0.5332 (4)	0.8304 (4)	0.0561 (7)
C2	0.83127 (11)	0.5846 (4)	0.7543 (5)	0.0595 (8)
H2	0.8309	0.6345	0.6196	0.071*
C3	0.87134 (11)	0.5624 (4)	0.8759 (5)	0.0612 (8)
C4	0.87339 (12)	0.4841 (4)	1.0761 (5)	0.0651 (8)
H4	0.9012	0.4679	1.1566	0.078*
C5	0.83396 (12)	0.4317 (4)	1.1521 (5)	0.0662 (9)
H5	0.8351	0.3769	1.2847	0.079*
C6	0.79214 (11)	0.4581 (4)	1.0363 (5)	0.0607 (8)
C8	0.74786 (12)	0.5520 (4)	0.6986 (5)	0.0616 (8)
H8	0.7481	0.5908	0.5596	0.074*
C9	0.66929 (11)	0.5123 (4)	0.6311 (5)	0.0598 (7)
C10	0.62906 (12)	0.5708 (4)	0.7062 (5)	0.0674 (8)
H10	0.6298	0.6195	0.8417	0.081*
C11	0.58855 (13)	0.5576 (5)	0.5832 (6)	0.0778 (10)
H11	0.5619	0.5972	0.6350	0.093*
C12	0.58717 (12)	0.4860 (5)	0.3835 (6)	0.0716 (9)
C13	0.62616 (13)	0.4247 (5)	0.3058 (5)	0.0707 (9)
H13	0.6248	0.3734	0.1713	0.085*
C14	0.66709 (12)	0.4392 (4)	0.4268 (5)	0.0637 (8)
H14	0.6935	0.4003	0.3729	0.076*
C15	0.94016 (13)	0.5208 (5)	0.7263 (6)	0.0748 (9)
N1	0.70971 (9)	0.5168 (3)	0.7683 (4)	0.0618 (7)
O1	0.75423 (9)	0.4102 (3)	1.1218 (4)	0.0773 (7)
H1	0.7320	0.4327	1.0380	0.116*
O2	0.91140 (8)	0.6360 (3)	0.8050 (4)	0.0756 (7)
F1	0.91975 (12)	0.4373 (4)	0.5572 (5)	0.1403 (12)
F2	0.97374 (9)	0.6120 (4)	0.6655 (5)	0.1174 (9)
F3	0.95437 (12)	0.3876 (5)	0.8491 (6)	0.1558 (15)
Cl1	0.53598 (4)	0.46496 (19)	0.22578 (19)	0.1103 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0635 (19)	0.0520 (15)	0.0530 (16)	−0.0008 (13)	0.0076 (13)	−0.0016 (12)
C2	0.068 (2)	0.0537 (15)	0.0575 (16)	−0.0002 (13)	0.0091 (15)	0.0024 (13)
C3	0.0584 (19)	0.0548 (16)	0.0713 (19)	−0.0048 (13)	0.0118 (15)	−0.0032 (13)
C4	0.067 (2)	0.0586 (17)	0.0674 (18)	0.0012 (14)	−0.0043 (15)	−0.0038 (14)
C5	0.081 (3)	0.0627 (18)	0.0551 (17)	0.0009 (15)	0.0063 (16)	−0.0006 (13)
C6	0.067 (2)	0.0583 (17)	0.0576 (17)	−0.0009 (14)	0.0121 (15)	−0.0030 (13)
C8	0.069 (2)	0.0602 (17)	0.0557 (16)	−0.0005 (14)	0.0073 (15)	0.0022 (13)
C9	0.063 (2)	0.0565 (15)	0.0609 (17)	−0.0012 (13)	0.0101 (15)	0.0027 (13)
C10	0.067 (2)	0.076 (2)	0.0608 (18)	0.0042 (16)	0.0156 (16)	−0.0032 (15)
C11	0.059 (2)	0.089 (2)	0.087 (2)	0.0072 (17)	0.0131 (18)	0.0024 (19)
C12	0.066 (2)	0.0692 (19)	0.077 (2)	−0.0015 (16)	−0.0024 (17)	0.0100 (17)
C13	0.076 (3)	0.074 (2)	0.0614 (18)	0.0006 (16)	0.0042 (17)	0.0013 (15)
C14	0.062 (2)	0.0690 (19)	0.0614 (18)	0.0028 (14)	0.0144 (15)	0.0015 (14)
C15	0.070 (2)	0.079 (2)	0.075 (2)	−0.0030 (19)	0.0089 (18)	0.0058 (19)
N1	0.0598 (17)	0.0655 (15)	0.0608 (15)	0.0022 (12)	0.0094 (13)	0.0018 (11)
O1	0.0702 (16)	0.1015 (17)	0.0622 (13)	−0.0015 (12)	0.0164 (11)	0.0150 (12)
O2	0.0702 (16)	0.0633 (13)	0.0952 (16)	−0.0058 (11)	0.0180 (13)	−0.0014 (11)
F1	0.137 (3)	0.158 (3)	0.130 (2)	−0.025 (2)	0.032 (2)	−0.063 (2)
F2	0.0774 (17)	0.126 (2)	0.154 (2)	−0.0122 (14)	0.0383 (16)	0.0144 (17)
F3	0.129 (3)	0.169 (3)	0.181 (3)	0.081 (2)	0.066 (2)	0.091 (2)
Cl1	0.0737 (8)	0.1402 (10)	0.1111 (9)	−0.0048 (6)	−0.0188 (6)	0.0037 (7)

Geometric parameters (Å, º) top

C1—C2	1.392 (4)	C9—N1	1.407 (4)
C1—C6	1.416 (4)	C10—C11	1.366 (5)
C1—C8	1.453 (4)	C10—H10	0.93
C2—C3	1.357 (5)	C11—C12	1.370 (5)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.391 (5)	C12—C13	1.376 (5)
C3—O2	1.416 (4)	C12—Cl1	1.736 (4)
C4—C5	1.363 (5)	C13—C14	1.371 (5)
C4—H4	0.93	C13—H13	0.93
C5—C6	1.387 (5)	C14—H14	0.93
C5—H5	0.93	C15—F3	1.280 (4)
C6—O1	1.343 (4)	C15—F2	1.285 (4)
C8—N1	1.282 (4)	C15—F1	1.323 (5)
C8—H8	0.93	C15—O2	1.324 (4)
C9—C10	1.394 (5)	O1—H1	0.82
C9—C14	1.400 (4)

C2—C1—C6	118.7 (3)	C11—C10—C9	120.8 (3)
C2—C1—C8	120.4 (3)	C11—C10—H10	119.6
C6—C1—C8	120.8 (3)	C9—C10—H10	119.6
C3—C2—C1	120.3 (3)	C10—C11—C12	119.9 (3)
C3—C2—H2	119.8	C10—C11—H11	120.1
C1—C2—H2	119.8	C12—C11—H11	120.1
C2—C3—C4	121.6 (3)	C11—C12—C13	120.7 (3)
C2—C3—O2	119.1 (3)	C11—C12—Cl1	120.7 (3)
C4—C3—O2	119.1 (3)	C13—C12—Cl1	118.6 (3)
C5—C4—C3	118.8 (3)	C14—C13—C12	119.9 (3)
C5—C4—H4	120.6	C14—C13—H13	120.0
C3—C4—H4	120.6	C12—C13—H13	120.0
C4—C5—C6	121.5 (3)	C13—C14—C9	120.3 (3)
C4—C5—H5	119.2	C13—C14—H14	119.8
C6—C5—H5	119.2	C9—C14—H14	119.8
O1—C6—C5	119.1 (3)	F3—C15—F2	110.6 (4)
O1—C6—C1	121.9 (3)	F3—C15—F1	104.5 (4)
C5—C6—C1	119.0 (3)	F2—C15—F1	106.8 (3)
N1—C8—C1	121.9 (3)	F3—C15—O2	114.8 (3)
N1—C8—H8	119.0	F2—C15—O2	110.1 (3)
C1—C8—H8	119.0	F1—C15—O2	109.6 (3)
C10—C9—C14	118.3 (3)	C8—N1—C9	120.8 (3)
C10—C9—N1	118.8 (3)	C6—O1—H1	109.5
C14—C9—N1	122.7 (3)	C15—O2—C3	118.7 (3)

C6—C1—C2—C3	0.1 (4)	C9—C10—C11—C12	0.0 (5)
C8—C1—C2—C3	−178.3 (3)	C10—C11—C12—C13	0.8 (5)
C1—C2—C3—C4	1.7 (4)	C10—C11—C12—Cl1	179.1 (3)
C1—C2—C3—O2	−172.5 (2)	C11—C12—C13—C14	−1.6 (5)
C2—C3—C4—C5	−1.1 (5)	Cl1—C12—C13—C14	−179.9 (2)
O2—C3—C4—C5	173.1 (3)	C12—C13—C14—C9	1.5 (5)
C3—C4—C5—C6	−1.3 (5)	C10—C9—C14—C13	−0.6 (4)
C4—C5—C6—O1	−177.5 (3)	N1—C9—C14—C13	174.8 (3)
C4—C5—C6—C1	3.0 (4)	C1—C8—N1—C9	−171.6 (3)
C2—C1—C6—O1	178.2 (3)	C10—C9—N1—C8	−146.5 (3)
C8—C1—C6—O1	−3.4 (4)	C14—C9—N1—C8	38.1 (4)
C2—C1—C6—C5	−2.4 (4)	F3—C15—O2—C3	−56.1 (5)
C8—C1—C6—C5	176.0 (3)	F2—C15—O2—C3	178.3 (3)
C2—C1—C8—N1	−175.6 (3)	F1—C15—O2—C3	61.2 (4)
C6—C1—C8—N1	6.0 (4)	C2—C3—O2—C15	−103.8 (4)
C14—C9—C10—C11	−0.2 (5)	C4—C3—O2—C15	81.9 (4)
N1—C9—C10—C11	−175.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.604 (4)	147
C14—H14···O1ⁱ	0.93	2.53	3.396 (5)	155
C2—H2···Cg1ⁱⁱ	0.93	2.77	3.496 (4)	135
C5—H5···Cg1ⁱⁱⁱ	0.93	2.98	3.713 (4)	136
C10—H10···Cg2^iv	0.93	2.94	3.644 (4)	133
C13—H13···Cg2^v	0.93	2.88	3.597 (4)	135

Symmetry codes: (i) x, y, z−1; (ii) x, −y−1/2, z−1/2; (iii) x, −y+1/2, z−3/2; (iv) x, −y−1/2, z−3/2; (v) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉ClF₃NO₂
M_r	315.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	29.612 (5), 7.195 (5), 6.375 (5)
β (°)	96.012 (5)
V (Å³)	1350.8 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.72 × 0.44 × 0.10

Data collection
Diffractometer	Stoe IPDS-II
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.844, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	11226, 2579, 1539
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.201, 1.04
No. of reflections	2579
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.33

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
O1—H1···N1	0.82	1.88	2.604 (4)	147
C14—H14···O1ⁱ	0.93	2.53	3.396 (5)	155
C2—H2···Cg1ⁱⁱ	0.93	2.77	3.496 (4)	135
C5—H5···Cg1ⁱⁱⁱ	0.93	2.98	3.713 (4)	136
C10—H10···Cg2^iv	0.93	2.94	3.644 (4)	133
C13—H13···Cg2^v	0.93	2.88	3.597 (4)	135

Symmetry codes: (i) x, y, z−1; (ii) x, −y−1/2, z−1/2; (iii) x, −y+1/2, z−3/2; (iv) x, −y−1/2, z−3/2; (v) 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 IPDSII diffractometer (purchased under grant No. F279 of the University Research Fund).

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