(E)-4-Meth­oxy-2-[3-(trifluoro­meth­yl)phenyl­imino­meth­yl]phenol

Keleşoğlu, Z.; Büyükgüngör, O.; Albayrak, Ç.; Odabaşoğlu, M.

doi:10.1107/S160053680905034X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3245-o3246

doi:10.1107/S160053680905034X

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(E)-4-Methoxy-2-[3-(trifluoromethyl)phenyliminomethyl]phenol

Zeynep Keleşoğlu,^a Orhan Büyükgüngör,^a ^* Çiğdem Albayrak ^b and Mustafa Odabaşoğlu ^c

^aDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, ^bSinop University, Sinop Faculty of Education, Sinop, Turkey, and ^cChemistry Program, Denizli Higher Vocational School, Pamukkale University, TR-20159 Denizli, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 5 November 2009; accepted 23 November 2009; online 28 November 2009)

The title compound, C₁₅H₁₂F₃NO₂, adopts the phenol–imine tautomeric form, with the H atom attached to oxygen rather than to nitrogen. There are two independent molecules aligned nearly parallel in the asymmetric unit with their trifloramethyl groups pointing in opposite directions. The dihedral angles between the aromatic rings are 40.43 (1)° in the first molecule and 36.12 (1)° in the second. Strong intramolecular O—H⋯N hydrogen bonding generates S(6) ring motifs. Weak intermolecular C—H⋯O hydrogen bonds link the independent molecules separately into sheets normal to [010]. In addition, C—H⋯π interactions are also observed. The F atoms of the trifluoromethyl groups are disordered over two sets of sites with refined site occupancies of 0.59 (2)/0.41 (2) and 0.62 (3)/0.38 (3), respectively.

Related literature

For the photochromic and thermochromic characteristics of Schiff base compounds, see: Williams (1972 ); Calligaris et al. (1972 ); Gavronic et al. (1996 ); Hadjoudis et al. (1987 ). For graph-set motifs, see: Bernstein et al. (1995 ). For related structures, see: Temel et al. (2007 ); Odabaşoğlu & Büyükgüngör (2006 ).

Experimental

Crystal data

C₁₅H₁₂F₃NO₂
M_r = 295.26
Monoclinic, P 2₁ /c
a = 13.4771 (7) Å
b = 6.4526 (2) Å
c = 31.7097 (15) Å
β = 92.647 (4)°
V = 2754.6 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.80 × 0.43 × 0.15 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.739, T_max = 0.944
23526 measured reflections
5197 independent reflections
3536 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.205
S = 1.07
5197 reflections
444 parameters
144 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.91 (4)	1.79 (4)	2.619 (4)	150 (4)
O1A—H1A⋯N1A	0.87 (4)	1.87 (4)	2.623 (3)	143 (4)
C10—H10⋯O1ⁱ	0.93	2.58	3.444 (3)	154
C10A—H10A⋯O1Aⁱ	0.93	2.54	3.413 (3)	157
C3—H3⋯Cg3ⁱⁱ	0.93	2.86	3.526 (3)	130
C3A—H3A⋯Cg1ⁱⁱ	0.93	2.88	3.518 (3)	127
C11—H11⋯Cg4ⁱⁱⁱ	0.93	2.85	3.529 (3)	131
C11A—H11A⋯Cg2ⁱⁱⁱ	0.93	2.97	3.646 (3)	131
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C9-C14, C1A–C6A and C9A–C14A 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905034X/si2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905034X/si2222Isup2.hkl

checkCIF report

Comment top

Most Schiff bases have antibacterial, anticancer, antinflammatory and antitoxic properties (Williams, 1972). In addition to that, Schiff bases have been used widely as ligands in the field of coordination chemistry (Calligaris et al., 1972). The Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Hadjoudis et al., 1987).

Photochromism is produced by an intramolecular proton transfer associated with a change in the π-electron configuration. Studies on photochromic compounds have been increasing ever since the potential applications of photochromic materials were realised in various areas, such as the control and measurement of radiation intensity, optical computers and display systems. Two types of intramolecular hydrogen bonds [either N—H···O (keto form) or N···H—O (enol form)] can exist in Schiff bases. The Schiff bases derived from salicyaldehyde always form the N···H–O type of hydrogen bonding, regardless of the nature of the N substituent (alkyl or aryl) (Gavronic et al., 1996).

The asymmetric unit of (I) contains two independent molecules aligned in opposite direction (Fig. 1.) and intermolecular hydrogen bonds C10—H10···O1 and C10A—H10A···O1A linked both independent molecules separately into sheets along [010] (Table 1. and Fig. 2.). The similar packing were observed in the structure (E)-3-[2-(Trifluoromethyl)phenyliminomethyl]-benzene-1,2-diol (Temel et al., 2007) but with O—H···O intermolecular hydrogen bonds. Intramolecular O—H···N hydrogen bonds generating S(6) ring motif (Bernstein et al., 1995) are observed in both molecules. The two mutual aromatic rings of the molecules in the asymmetric unit inclined at 2.56 (2)° and 12.37 (12)°. The dihedral angles between the two benzene rings are 40.43 (1)° in the first molecule and 36.12 (1)° in the second molecule numbered with label A.

The crystal packing is also stabilized by C11—H11···Cg4, C3A—H3A···Cg1 and C11A—H11A···Cg2 π-ring interactions (Fig.3, Table 1). Similar results were observed in 3-[3-(Trifluoromethyl)anilino]isobenzofuran-1(3H)-one (Odabaşoğlu & Büyükgüngör (2006).

The CF3 group shows rotational disorder; the F atoms of the trifluoromethyl groups are disordered over two positions with refined site occupancies of 0.59 (2)/0.41 (2) and 0.62 (3)/0.38 (3), respectively.

Related literature top

For the photochromic and thermochromic characteristics of Schiff base compounds, see: Williams (1972); Calligaris et al. (1972); Gavronic et al. (1996); Hadjoudis et al. (1987). For graph-set motifs, see: Bernstein et al. (1995). For related structures, see: Temel et al. (2007); Odabaşoğlu & Büyükgüngör (2006). Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C9-C14, C1A–C6A and C9A–C14A rings, respectively.

Experimental top

The compound(I) was prepared by stirring for 1 h under reflux, the mixture of 5-methoxysalicylaldehyde (0.5 g, 3.3 mmol) in ethanol (20 ml) and 3-trifluoromethylaniline (0.53 g, 3.3 mmol) in ethanol (20 ml). The crystals suitable for X-ray analysis were obtained from methanol by slow evaporation (yield; 74%, m.p.; 344–345 K).

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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. An ORTEP view of (I), with the atom-numbering scheme and 20% probability displacement ellipsoids. The minor disorder components of the trifluoromethyl F atoms were omitted. Dashed lines indicate H-bonds.
	Fig. 2. A packing diagram for (I), showing the C—H···O hydrogen bonds. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity. [Symmetry codes; (i): x,-1 + y,z].
	Fig. 3. A packing diagram for (I), showing the C—H···π interactions. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity. [Symmetry codes; (i): 1 - x, 1/2 + y, 1/2 - z; (ii): 1 - x, -1/2 + y, 1/2 - z]. (Cg1,Cg2 and Cg3, Cg4 are the centroids of the C1—C6, C9—C14; C1A—C6A, C9A—C14A rings, respectively).

(E)-4-Methoxy-2-[3-(trifluoromethyl)phenyliminomethyl]phenol top

Crystal data top

C₁₅H₁₂F₃NO₂	F(000) = 1216
M_r = 295.26	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20067 reflections
a = 13.4771 (7) Å	θ = 1.3–25.7°
b = 6.4526 (2) Å	µ = 0.12 mm⁻¹
c = 31.7097 (15) Å	T = 296 K
β = 92.647 (4)°	Prism, yellow
V = 2754.6 (2) Å³	0.80 × 0.43 × 0.15 mm
Z = 8

Data collection top

Stoe IPDS II diffractometer	5197 independent reflections
Radiation source: fine-focus sealed tube	3536 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.075
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.7°, θ_min = 1.3°
rotation method scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
T_min = 0.739, T_max = 0.944	l = −38→38
23526 measured 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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.205	w = 1/[σ²(F_o²) + (0.0875P)² + 1.1131P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
5197 reflections	Δρ_max = 0.20 e Å⁻³
444 parameters	Δρ_min = −0.25 e Å⁻³
144 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: 0.0018 (5)

Crystal data top

C₁₅H₁₂F₃NO₂	V = 2754.6 (2) Å³
M_r = 295.26	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4771 (7) Å	µ = 0.12 mm⁻¹
b = 6.4526 (2) Å	T = 296 K
c = 31.7097 (15) Å	0.80 × 0.43 × 0.15 mm
β = 92.647 (4)°

Data collection top

Stoe IPDS II diffractometer	5197 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3536 reflections with I > 2σ(I)
T_min = 0.739, T_max = 0.944	R_int = 0.075
23526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	144 restraints
wR(F²) = 0.205	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.20 e Å⁻³
5197 reflections	Δρ_min = −0.25 e Å⁻³
444 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	Occ. (<1)
F1A	0.1216 (9)	0.4505 (8)	0.46713 (17)	0.126 (3)	0.592 (15)
F2A	0.1877 (10)	0.1908 (17)	0.5018 (2)	0.155 (4)	0.592 (15)
F3A	0.0307 (7)	0.218 (2)	0.4785 (4)	0.187 (5)	0.592 (15)
F1B	0.1963 (14)	0.406 (2)	0.4751 (4)	0.165 (5)	0.408 (15)
F2B	0.1215 (13)	0.1269 (16)	0.5008 (3)	0.126 (4)	0.408 (15)
F3B	0.0359 (10)	0.324 (3)	0.4722 (6)	0.181 (6)	0.408 (15)
C1A	0.61622 (19)	0.2839 (4)	0.27472 (8)	0.0492 (6)
C2A	0.6470 (2)	0.4936 (5)	0.27532 (9)	0.0522 (7)
C3A	0.6768 (2)	0.5824 (5)	0.31314 (9)	0.0596 (7)
H3A	0.6973	0.7201	0.3137	0.072*
C4A	0.6770 (2)	0.4718 (5)	0.35037 (10)	0.0629 (8)
H4A	0.6974	0.5352	0.3756	0.075*
C5A	0.6471 (2)	0.2668 (5)	0.35018 (9)	0.0607 (8)
C6A	0.6160 (2)	0.1754 (5)	0.31277 (8)	0.0564 (7)
H6A	0.5944	0.0385	0.3128	0.068*
C7A	0.6930 (4)	0.2192 (8)	0.42341 (11)	0.1045 (14)
H7A1	0.6875	0.1179	0.4454	0.157*
H7A2	0.6605	0.3448	0.4314	0.157*
H7A3	0.7618	0.2469	0.4192	0.157*
C8A	0.59249 (19)	0.1754 (5)	0.23556 (8)	0.0517 (7)
H8A	0.5768	0.0352	0.2365	0.062*
C9A	0.5837 (2)	0.1543 (4)	0.16155 (8)	0.0502 (6)
C10A	0.6170 (2)	−0.0492 (5)	0.15797 (9)	0.0561 (7)
H10A	0.6420	−0.1193	0.1818	0.067*
C11A	0.6127 (2)	−0.1466 (5)	0.11934 (10)	0.0631 (8)
H11A	0.6342	−0.2831	0.1174	0.076*
C12A	0.5771 (2)	−0.0451 (5)	0.08346 (10)	0.0636 (8)
H12A	0.5743	−0.1118	0.0574	0.076*
C13A	0.5455 (2)	0.1581 (5)	0.08704 (9)	0.0596 (7)
C14A	0.5483 (2)	0.2566 (5)	0.12565 (9)	0.0567 (7)
H14A	0.5263	0.3927	0.1276	0.068*
C15A	0.5104 (3)	0.2720 (5)	0.04844 (10)	0.0829 (11)
N1A	0.59247 (17)	0.2674 (4)	0.19956 (7)	0.0529 (6)
O1A	0.64877 (18)	0.6071 (4)	0.23935 (7)	0.0691 (6)
O2A	0.6472 (2)	0.1424 (4)	0.38544 (7)	0.0873 (8)
C1	0.10504 (19)	0.2748 (5)	0.24086 (9)	0.0527 (7)
C2	0.1374 (2)	0.4839 (5)	0.23806 (9)	0.0564 (7)
C3	0.1381 (2)	0.5767 (5)	0.19883 (11)	0.0649 (8)
H3	0.1589	0.7136	0.1968	0.078*
C4	0.1089 (2)	0.4713 (6)	0.16290 (11)	0.0692 (9)
H4	0.1098	0.5373	0.1369	0.083*
C5	0.0776 (2)	0.2655 (6)	0.16503 (10)	0.0642 (8)
C6	0.0749 (2)	0.1719 (5)	0.20390 (9)	0.0584 (7)
H6	0.0523	0.0361	0.2055	0.070*
C7	0.0736 (3)	0.2186 (9)	0.09038 (11)	0.1054 (15)
H7A	0.0501	0.1211	0.0694	0.158*
H7B	0.1443	0.2333	0.0892	0.158*
H7C	0.0424	0.3505	0.0852	0.158*
C8	0.1080 (2)	0.1653 (5)	0.28078 (9)	0.0549 (7)
H8	0.0905	0.0258	0.2812	0.066*
C9	0.1463 (2)	0.1420 (5)	0.35335 (9)	0.0559 (7)
C10	0.1841 (2)	−0.0589 (5)	0.35468 (10)	0.0620 (8)
H10	0.1978	−0.1267	0.3297	0.074*
C11	0.2011 (3)	−0.1575 (6)	0.39286 (11)	0.0741 (9)
H11	0.2256	−0.2922	0.3935	0.089*
C12	0.1821 (3)	−0.0587 (6)	0.42978 (11)	0.0795 (10)
H12	0.1941	−0.1258	0.4555	0.095*
C13	0.1451 (3)	0.1413 (6)	0.42881 (10)	0.0749 (9)
C14	0.1274 (2)	0.2419 (5)	0.39071 (9)	0.0655 (8)
H14	0.1028	0.3766	0.3902	0.079*
C15	0.1269 (5)	0.2510 (8)	0.46891 (13)	0.1131 (16)
N1	0.13402 (17)	0.2560 (4)	0.31550 (7)	0.0555 (6)
O1	0.16842 (17)	0.5928 (4)	0.27249 (8)	0.0710 (6)
O2	0.0501 (2)	0.1466 (5)	0.13076 (7)	0.0893 (8)
F4A	0.5051 (12)	0.4750 (10)	0.0524 (3)	0.089 (2)	0.62 (3)
F5A	0.5747 (12)	0.2314 (18)	0.0164 (3)	0.109 (3)	0.62 (3)
F6A	0.4221 (8)	0.220 (2)	0.0334 (4)	0.126 (3)	0.62 (3)
F4B	0.5467 (18)	0.466 (2)	0.0490 (6)	0.094 (4)	0.38 (3)
F5B	0.5269 (19)	0.191 (2)	0.0124 (3)	0.104 (4)	0.38 (3)
F6B	0.4096 (8)	0.275 (4)	0.0467 (8)	0.137 (6)	0.38 (3)
H1	0.162 (3)	0.506 (7)	0.2948 (13)	0.095 (14)*
H1A	0.627 (3)	0.535 (7)	0.2175 (13)	0.091 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.211 (8)	0.094 (4)	0.074 (3)	0.016 (4)	0.022 (4)	−0.028 (2)
F2A	0.204 (8)	0.175 (7)	0.083 (4)	0.046 (6)	−0.034 (4)	−0.028 (4)
F3A	0.230 (8)	0.181 (8)	0.159 (7)	−0.003 (6)	0.113 (6)	−0.048 (6)
F1B	0.216 (10)	0.161 (9)	0.120 (6)	−0.031 (8)	0.029 (7)	−0.066 (6)
F2B	0.189 (9)	0.140 (7)	0.051 (4)	0.014 (6)	0.029 (5)	0.005 (4)
F3B	0.219 (10)	0.174 (11)	0.154 (8)	0.067 (8)	0.059 (7)	−0.026 (8)
C1A	0.0495 (14)	0.0506 (16)	0.0478 (14)	0.0021 (12)	0.0037 (11)	0.0036 (12)
C2A	0.0495 (14)	0.0529 (17)	0.0542 (16)	0.0006 (12)	0.0020 (11)	0.0071 (13)
C3A	0.0552 (16)	0.0545 (18)	0.0692 (19)	−0.0009 (13)	0.0029 (13)	−0.0075 (14)
C4A	0.0592 (17)	0.076 (2)	0.0533 (16)	−0.0008 (15)	−0.0001 (13)	−0.0100 (15)
C5A	0.0610 (17)	0.072 (2)	0.0489 (15)	0.0024 (15)	0.0060 (12)	0.0053 (14)
C6A	0.0654 (17)	0.0543 (17)	0.0500 (15)	−0.0006 (14)	0.0063 (12)	0.0068 (13)
C7A	0.131 (4)	0.130 (4)	0.052 (2)	0.001 (3)	−0.009 (2)	0.008 (2)
C8A	0.0520 (15)	0.0523 (17)	0.0507 (15)	−0.0048 (12)	0.0012 (11)	0.0065 (12)
C9A	0.0506 (14)	0.0516 (16)	0.0480 (14)	−0.0060 (12)	−0.0010 (11)	0.0061 (12)
C10A	0.0616 (17)	0.0522 (17)	0.0539 (16)	0.0013 (13)	−0.0029 (12)	0.0081 (13)
C11A	0.076 (2)	0.0478 (17)	0.0650 (18)	0.0028 (15)	−0.0039 (14)	0.0017 (14)
C12A	0.081 (2)	0.0553 (19)	0.0534 (16)	−0.0049 (16)	−0.0049 (14)	−0.0045 (14)
C13A	0.079 (2)	0.0516 (18)	0.0479 (15)	0.0000 (15)	−0.0057 (13)	0.0042 (13)
C14A	0.0707 (18)	0.0469 (17)	0.0521 (15)	0.0007 (14)	−0.0017 (13)	0.0047 (12)
C15A	0.132 (4)	0.060 (2)	0.0557 (19)	0.008 (2)	−0.015 (2)	−0.0002 (16)
N1A	0.0560 (13)	0.0553 (14)	0.0470 (12)	−0.0017 (11)	−0.0007 (10)	0.0053 (10)
O1A	0.0904 (16)	0.0550 (14)	0.0612 (13)	−0.0100 (11)	−0.0048 (11)	0.0140 (11)
O2A	0.117 (2)	0.098 (2)	0.0461 (12)	−0.0097 (15)	−0.0007 (12)	0.0132 (12)
C1	0.0472 (14)	0.0555 (18)	0.0560 (16)	−0.0006 (12)	0.0074 (11)	−0.0035 (13)
C2	0.0504 (15)	0.0551 (18)	0.0643 (18)	−0.0013 (13)	0.0082 (12)	−0.0015 (14)
C3	0.0597 (17)	0.0587 (19)	0.077 (2)	−0.0005 (14)	0.0098 (15)	0.0070 (16)
C4	0.0597 (18)	0.080 (2)	0.0683 (19)	0.0061 (16)	0.0077 (14)	0.0163 (18)
C5	0.0538 (16)	0.080 (2)	0.0587 (17)	−0.0008 (16)	0.0008 (13)	−0.0015 (16)
C6	0.0547 (16)	0.0586 (18)	0.0622 (17)	−0.0046 (13)	0.0052 (13)	0.0003 (14)
C7	0.110 (3)	0.150 (4)	0.057 (2)	−0.004 (3)	0.002 (2)	0.000 (2)
C8	0.0522 (15)	0.0533 (17)	0.0596 (17)	−0.0017 (13)	0.0062 (12)	−0.0023 (13)
C9	0.0528 (15)	0.0599 (19)	0.0553 (16)	−0.0041 (14)	0.0065 (12)	−0.0040 (14)
C10	0.0619 (17)	0.0594 (19)	0.0648 (18)	0.0021 (14)	0.0035 (14)	−0.0109 (15)
C11	0.079 (2)	0.063 (2)	0.081 (2)	0.0049 (17)	0.0050 (17)	0.0017 (18)
C12	0.096 (3)	0.075 (2)	0.067 (2)	0.004 (2)	0.0064 (18)	0.0115 (18)
C13	0.093 (2)	0.076 (2)	0.0571 (18)	0.0038 (19)	0.0165 (16)	−0.0019 (16)
C14	0.078 (2)	0.0609 (19)	0.0581 (17)	0.0026 (16)	0.0119 (14)	−0.0062 (14)
C15	0.169 (5)	0.110 (4)	0.062 (2)	0.017 (4)	0.020 (3)	0.005 (2)
N1	0.0572 (13)	0.0584 (15)	0.0511 (13)	−0.0012 (11)	0.0063 (10)	−0.0062 (11)
O1	0.0809 (15)	0.0589 (14)	0.0735 (15)	−0.0107 (11)	0.0076 (12)	−0.0116 (12)
O2	0.1061 (19)	0.109 (2)	0.0523 (13)	−0.0176 (16)	−0.0021 (12)	−0.0022 (13)
F4A	0.143 (6)	0.060 (3)	0.063 (3)	0.019 (3)	−0.010 (4)	0.0089 (19)
F5A	0.159 (7)	0.117 (5)	0.052 (3)	0.019 (4)	0.010 (3)	0.020 (3)
F6A	0.149 (6)	0.120 (6)	0.102 (5)	−0.017 (4)	−0.072 (4)	0.019 (4)
F4B	0.137 (9)	0.065 (5)	0.077 (5)	−0.011 (5)	−0.020 (7)	0.023 (4)
F5B	0.158 (10)	0.091 (6)	0.059 (4)	0.013 (6)	−0.028 (5)	−0.012 (4)
F6B	0.151 (8)	0.134 (10)	0.118 (10)	0.021 (6)	−0.064 (6)	0.019 (7)

Geometric parameters (Å, º) top

F1A—C15	1.290 (6)	C15A—F6A	1.306 (7)
F2A—C15	1.352 (7)	C15A—F4A	1.318 (7)
F3A—C15	1.362 (9)	C15A—F4B	1.345 (9)
F1B—C15	1.376 (9)	C15A—F6B	1.358 (10)
F2B—C15	1.295 (7)	C15A—F5A	1.389 (7)
F3B—C15	1.323 (10)	O1A—H1A	0.87 (4)
C1A—C6A	1.395 (4)	C1—C6	1.391 (4)
C1A—C2A	1.415 (4)	C1—C2	1.422 (4)
C1A—C8A	1.448 (4)	C1—C8	1.449 (4)
C2A—O1A	1.356 (3)	C2—O1	1.348 (4)
C2A—C3A	1.372 (4)	C2—C3	1.381 (4)
C3A—C4A	1.379 (4)	C3—C4	1.369 (5)
C3A—H3A	0.9300	C3—H3	0.9300
C4A—C5A	1.383 (5)	C4—C5	1.396 (5)
C4A—H4A	0.9300	C4—H4	0.9300
C5A—C6A	1.373 (4)	C5—O2	1.367 (4)
C5A—O2A	1.377 (4)	C5—C6	1.375 (4)
C6A—H6A	0.9300	C6—H6	0.9300
C7A—O2A	1.417 (4)	C7—O2	1.412 (4)
C7A—H7A1	0.9600	C7—H7A	0.9600
C7A—H7A2	0.9600	C7—H7B	0.9600
C7A—H7A3	0.9600	C7—H7C	0.9600
C8A—N1A	1.287 (3)	C8—N1	1.282 (4)
C8A—H8A	0.9300	C8—H8	0.9300
C9A—C14A	1.382 (4)	C9—C14	1.383 (4)
C9A—C10A	1.393 (4)	C9—C10	1.393 (4)
C9A—N1A	1.410 (3)	C9—N1	1.411 (4)
C10A—C11A	1.376 (4)	C10—C11	1.377 (5)
C10A—H10A	0.9300	C10—H10	0.9300
C11A—C12A	1.380 (4)	C11—C12	1.367 (5)
C11A—H11A	0.9300	C11—H11	0.9300
C12A—C13A	1.385 (4)	C12—C13	1.383 (5)
C12A—H12A	0.9300	C12—H12	0.9300
C13A—C14A	1.378 (4)	C13—C14	1.383 (5)
C13A—C15A	1.486 (4)	C13—C15	1.486 (6)
C14A—H14A	0.9300	C14—H14	0.9300
C15A—F5B	1.285 (9)	O1—H1	0.91 (4)

C6A—C1A—C2A	118.7 (3)	C6—C1—C8	119.9 (3)
C6A—C1A—C8A	119.3 (3)	C2—C1—C8	121.4 (3)
C2A—C1A—C8A	121.8 (2)	O1—C2—C3	119.2 (3)
O1A—C2A—C3A	119.6 (3)	O1—C2—C1	121.9 (3)
O1A—C2A—C1A	121.4 (3)	C3—C2—C1	118.8 (3)
C3A—C2A—C1A	119.0 (3)	C4—C3—C2	121.4 (3)
C2A—C3A—C4A	121.4 (3)	C4—C3—H3	119.3
C2A—C3A—H3A	119.3	C2—C3—H3	119.3
C4A—C3A—H3A	119.3	C3—C4—C5	120.5 (3)
C3A—C4A—C5A	120.1 (3)	C3—C4—H4	119.7
C3A—C4A—H4A	119.9	C5—C4—H4	119.7
C5A—C4A—H4A	119.9	O2—C5—C6	116.7 (3)
C6A—C5A—O2A	116.1 (3)	O2—C5—C4	124.5 (3)
C6A—C5A—C4A	119.5 (3)	C6—C5—C4	118.8 (3)
O2A—C5A—C4A	124.4 (3)	C5—C6—C1	121.8 (3)
C5A—C6A—C1A	121.3 (3)	C5—C6—H6	119.1
C5A—C6A—H6A	119.4	C1—C6—H6	119.1
C1A—C6A—H6A	119.4	O2—C7—H7A	109.5
O2A—C7A—H7A1	109.5	O2—C7—H7B	109.5
O2A—C7A—H7A2	109.5	H7A—C7—H7B	109.5
H7A1—C7A—H7A2	109.5	O2—C7—H7C	109.5
O2A—C7A—H7A3	109.5	H7A—C7—H7C	109.5
H7A1—C7A—H7A3	109.5	H7B—C7—H7C	109.5
H7A2—C7A—H7A3	109.5	N1—C8—C1	121.5 (3)
N1A—C8A—C1A	121.9 (3)	N1—C8—H8	119.2
N1A—C8A—H8A	119.1	C1—C8—H8	119.2
C1A—C8A—H8A	119.1	C14—C9—C10	119.3 (3)
C14A—C9A—C10A	118.9 (3)	C14—C9—N1	117.8 (3)
C14A—C9A—N1A	118.0 (3)	C10—C9—N1	122.7 (3)
C10A—C9A—N1A	122.9 (2)	C11—C10—C9	120.1 (3)
C11A—C10A—C9A	120.2 (3)	C11—C10—H10	119.9
C11A—C10A—H10A	119.9	C9—C10—H10	119.9
C9A—C10A—H10A	119.9	C12—C11—C10	120.5 (3)
C10A—C11A—C12A	121.1 (3)	C12—C11—H11	119.8
C10A—C11A—H11A	119.5	C10—C11—H11	119.8
C12A—C11A—H11A	119.5	C11—C12—C13	119.8 (3)
C11A—C12A—C13A	118.6 (3)	C11—C12—H12	120.1
C11A—C12A—H12A	120.7	C13—C12—H12	120.1
C13A—C12A—H12A	120.7	C14—C13—C12	120.3 (3)
C14A—C13A—C12A	120.9 (3)	C14—C13—C15	119.7 (4)
C14A—C13A—C15A	119.9 (3)	C12—C13—C15	119.9 (3)
C12A—C13A—C15A	119.2 (3)	C13—C14—C9	119.9 (3)
C13A—C14A—C9A	120.4 (3)	C13—C14—H14	120.0
C13A—C14A—H14A	119.8	C9—C14—H14	120.0
C9A—C14A—H14A	119.8	F1A—C15—F2B	130.2 (6)
F5B—C15A—F6A	76.3 (8)	F1A—C15—F3B	66.3 (8)
F5B—C15A—F4A	120.2 (8)	F2B—C15—F3B	94.1 (11)
F6A—C15A—F4A	103.8 (7)	F1A—C15—F2A	110.6 (6)
F5B—C15A—F4B	108.3 (10)	F3B—C15—F2A	124.9 (10)
F6A—C15A—F4B	124.8 (9)	F1A—C15—F3A	96.5 (8)
F5B—C15A—F6B	100.6 (9)	F2B—C15—F3A	68.9 (8)
F4A—C15A—F6B	86.0 (9)	F2A—C15—F3A	109.4 (8)
F4B—C15A—F6B	110.4 (11)	F1A—C15—F1B	47.0 (7)
F6A—C15A—F5A	105.9 (6)	F2B—C15—F1B	113.6 (8)
F4A—C15A—F5A	107.2 (6)	F3B—C15—F1B	111.0 (11)
F4B—C15A—F5A	87.0 (9)	F2A—C15—F1B	73.5 (8)
F6B—C15A—F5A	129.1 (8)	F3A—C15—F1B	136.9 (9)
F5B—C15A—C13A	118.0 (7)	F1A—C15—C13	116.7 (4)
F6A—C15A—C13A	115.0 (6)	F2B—C15—C13	113.1 (6)
F4A—C15A—C13A	115.4 (5)	F3B—C15—C13	115.3 (10)
F4B—C15A—C13A	110.4 (8)	F2A—C15—C13	113.9 (5)
F6B—C15A—C13A	108.6 (9)	F3A—C15—C13	108.2 (6)
F5A—C15A—C13A	108.9 (5)	F1B—C15—C13	109.3 (6)
C8A—N1A—C9A	121.1 (3)	C8—N1—C9	120.6 (3)
C2A—O1A—H1A	111 (3)	C2—O1—H1	106 (3)
C5A—O2A—C7A	118.1 (3)	C5—O2—C7	118.2 (3)
C6—C1—C2	118.6 (3)

C6A—C1A—C2A—O1A	−180.0 (3)	C6—C1—C2—O1	−179.4 (3)
C8A—C1A—C2A—O1A	4.9 (4)	C8—C1—C2—O1	−2.7 (4)
C6A—C1A—C2A—C3A	0.8 (4)	C6—C1—C2—C3	−0.3 (4)
C8A—C1A—C2A—C3A	−174.3 (3)	C8—C1—C2—C3	176.4 (3)
O1A—C2A—C3A—C4A	−179.4 (3)	O1—C2—C3—C4	178.9 (3)
C1A—C2A—C3A—C4A	−0.1 (4)	C1—C2—C3—C4	−0.3 (4)
C2A—C3A—C4A—C5A	0.1 (5)	C2—C3—C4—C5	−0.2 (5)
C3A—C4A—C5A—C6A	−0.8 (4)	C3—C4—C5—O2	−177.9 (3)
C3A—C4A—C5A—O2A	178.2 (3)	C3—C4—C5—C6	1.2 (5)
O2A—C5A—C6A—C1A	−177.6 (3)	O2—C5—C6—C1	177.3 (3)
C4A—C5A—C6A—C1A	1.5 (5)	C4—C5—C6—C1	−1.8 (4)
C2A—C1A—C6A—C5A	−1.5 (4)	C2—C1—C6—C5	1.4 (4)
C8A—C1A—C6A—C5A	173.8 (3)	C8—C1—C6—C5	−175.4 (3)
C6A—C1A—C8A—N1A	−179.4 (3)	C6—C1—C8—N1	−179.0 (3)
C2A—C1A—C8A—N1A	−4.3 (4)	C2—C1—C8—N1	4.3 (4)
C14A—C9A—C10A—C11A	−1.1 (4)	C14—C9—C10—C11	0.8 (4)
N1A—C9A—C10A—C11A	−175.4 (3)	N1—C9—C10—C11	175.4 (3)
C9A—C10A—C11A—C12A	0.9 (5)	C9—C10—C11—C12	−0.7 (5)
C10A—C11A—C12A—C13A	0.1 (5)	C10—C11—C12—C13	0.3 (6)
C11A—C12A—C13A—C14A	−0.8 (5)	C11—C12—C13—C14	−0.1 (6)
C11A—C12A—C13A—C15A	177.8 (3)	C11—C12—C13—C15	−178.4 (4)
C12A—C13A—C14A—C9A	0.6 (5)	C12—C13—C14—C9	0.3 (5)
C15A—C13A—C14A—C9A	−178.0 (3)	C15—C13—C14—C9	178.5 (4)
C10A—C9A—C14A—C13A	0.4 (4)	C10—C9—C14—C13	−0.6 (5)
N1A—C9A—C14A—C13A	174.9 (3)	N1—C9—C14—C13	−175.5 (3)
C14A—C13A—C15A—F5B	166.6 (13)	C14—C13—C15—F1A	−18.4 (9)
C12A—C13A—C15A—F5B	−12.0 (14)	C12—C13—C15—F1A	159.9 (8)
C14A—C13A—C15A—F6A	−106.2 (9)	C14—C13—C15—F2B	163.3 (10)
C12A—C13A—C15A—F6A	75.2 (9)	C12—C13—C15—F2B	−18.5 (11)
C14A—C13A—C15A—F4A	14.6 (10)	C14—C13—C15—F3B	56.6 (12)
C12A—C13A—C15A—F4A	−164.0 (9)	C12—C13—C15—F3B	−125.1 (12)
C14A—C13A—C15A—F4B	41.4 (14)	C14—C13—C15—F2A	−149.1 (9)
C12A—C13A—C15A—F4B	−137.3 (13)	C12—C13—C15—F2A	29.1 (10)
C14A—C13A—C15A—F6B	−79.9 (13)	C14—C13—C15—F3A	89.0 (9)
C12A—C13A—C15A—F6B	101.5 (12)	C12—C13—C15—F3A	−92.7 (9)
C14A—C13A—C15A—F5A	135.2 (8)	C14—C13—C15—F1B	−69.1 (11)
C12A—C13A—C15A—F5A	−43.4 (9)	C12—C13—C15—F1B	109.1 (11)
C1A—C8A—N1A—C9A	170.5 (2)	C1—C8—N1—C9	−173.4 (2)
C14A—C9A—N1A—C8A	156.8 (3)	C14—C9—N1—C8	−149.7 (3)
C10A—C9A—N1A—C8A	−28.8 (4)	C10—C9—N1—C8	35.6 (4)
C6A—C5A—O2A—C7A	170.3 (3)	C6—C5—O2—C7	−165.4 (3)
C4A—C5A—O2A—C7A	−8.7 (5)	C4—C5—O2—C7	13.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (4)	1.79 (4)	2.619 (4)	150 (4)
O1A—H1A···N1A	0.87 (4)	1.87 (4)	2.623 (3)	143 (4)
C10—H10···O1ⁱ	0.93	2.58	3.444 (3)	154
C10A—H10A···O1Aⁱ	0.93	2.54	3.413 (3)	157
C3—H3···Cg3ⁱⁱ	0.93	2.86	3.526 (3)	130
C3A—H3A···Cg1ⁱⁱ	0.93	2.88	3.518 (3)	127
C11—H11···Cg4ⁱⁱⁱ	0.93	2.85	3.529 (3)	131
C11A—H11A···Cg2ⁱⁱⁱ	0.93	2.97	3.646 (3)	131

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂F₃NO₂
M_r	295.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.4771 (7), 6.4526 (2), 31.7097 (15)
β (°)	92.647 (4)
V (Å³)	2754.6 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.80 × 0.43 × 0.15

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.739, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	23526, 5197, 3536
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.205, 1.07
No. of reflections	5197
No. of parameters	444
No. of restraints	144
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

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) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (4)	1.79 (4)	2.619 (4)	150 (4)
O1A—H1A···N1A	0.87 (4)	1.87 (4)	2.623 (3)	143 (4)
C10—H10···O1ⁱ	0.93	2.58	3.444 (3)	154
C10A—H10A···O1Aⁱ	0.93	2.54	3.413 (3)	157
C3—H3···Cg3ⁱⁱ	0.93	2.86	3.526 (3)	130
C3A—H3A···Cg1ⁱⁱ	0.93	2.88	3.518 (3)	127
C11—H11···Cg4ⁱⁱⁱ	0.93	2.85	3.529 (3)	131
C11A—H11A···Cg2ⁱⁱⁱ	0.93	2.97	3.646 (3)	131

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, 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 II diffractometer (purchased under grant F.279 of the University Research Fund).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Calligaris, M., Nardin, G. & Randaccio, L. (1972). Coord. Chem. Rev. 7, 385–403. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gavronic, M., Kaitner, B. & Mestrovic, J. (1996). J. Chem. Crystallogr. 26, 836–837. Google Scholar
Hadjoudis, E., Vittorakis, M., Moustakali, I. & Mavridis, I. (1987). Tetrahedron, 43, 1345–1360. CrossRef CAS Web of Science Google Scholar
Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o4151–o4153. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Temel, E., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2007). Acta Cryst. E63, o374–o376. Web of Science CSD CrossRef IUCr Journals Google Scholar
Williams, D. R. (1972). Chem. Rev. 72, 203–213. CrossRef CAS PubMed Web of Science Google Scholar