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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 5| May 2016| x160797
doi:10.1107/S2414314616007975

2-Amino-3-((E)-{[3-(tri­fluoro­meth­yl)phen­yl]imino}­meth­yl)-4H-chromen-4-one

Şehriman Atalay,a* Semra Gerçeker,a Seher Meralb and Ayşen Alaman Ağarb

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 May 2016; accepted 16 May 2016; online 20 May 2016)

In the title compound, C17H11F3N2O2, the dihedral angle between the chromene ring system and the benzene ring is 19.19 (6)°, and an intra­molecular N—H⋯N hydrogen bond closes an S(6) ring. In the crystal, mol­ecules are linked into [100] C(6) chains by N—H⋯O hydrogen bonds.

CCDC reference: 1478497

Similar articles
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[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Schiff bases of chromone compounds are known as anti­cancer agents (Kawase et al., 2007[Kawase, M., Tanaka, T., Kan, H., Tani, S., Nakashima, H. & Sakagami, H. (2007). In Vivo, 21, 829-834.], Barath et al., 2006[Barath, Z., Radices, R., Spengler, G., Ocsovski, I., Kawase, M., Motohashi, N., Shirataki, Y., Shah, A. & Molnar, J. (2006). In Vivo, 20, 645-000.]). As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).

The dihedral angle between the C2–C7 and C9/C10/O1/C11–C17 ring systems is 19.19 (6)° (Fig. 1[link]); the maximum deviations are 0.012 (2) Å for atom C5 and 0.029 (2) Å for atom C17, respectively. The bond lengths of the imino group atoms [N1—C6 = 1.420 (3) Å and N1—C8 = 1.275 (3) Å] are consistent with corresponding distances in related structures, i.e. (E)-4-[(4-chloro­phenyl­imino)­meth­yl]benzene-1,2,3-triol (Karabıyık et al., 2008[Karabıyık, H., Ocak-Ískeleli, N., Petek, H., Albayrak, C. & Ağar, E. (2008). J. Mol. Struct. 873, 130-136.]) and (Z)-4-({(Z)-[2-oxonaphthalen-1(2H)-yl­idene]meth­yl}amino)-N-[thia­zol-2(3H)-yl­idene]benzene­sulfonamide (Köysal et al., 2015[Köysal, Y., Bülbül, H., Dege, N., Macit, M. & Alaman, A. A. (2015). Crystallogr. Rep. 60, 1001-1005.]). An intra­molecular N2—H2A⋯N1 hydrogen bond (Table 1[link]) closes an R(6) ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2A⋯N1 0.85 (2) 2.06 (2) 2.727 (2) 134.4 (16)
N2—H2B⋯O2i 0.90 (2) 1.84 (2) 2.745 (2) 178 (2)
Symmetry code: (i) x+1, y, z.
[Figure 1]
Figure 1
The mol­ecular structure of the title mol­ecule, with displacement ellipsoids drawn at the 30% probability level.

In the crystal, N2—H2B⋯O2 hydrogen bonds (Fig. 2[link]) link the mol­ecules into [100] C(6) chains.

[Figure 2]
Figure 2
Packing diagram of the title compound, viewed along the b axis.

Synthesis and crystallization

A mixture of a solution containing 2-amino-4-oxo-4H-chromene-3-carbaldehyde (0.0076 g 0.040 mmol) in 20 ml ethanol and a solution containing 3-(tri­fluoro­meth­yl)aniline (0.0065 g, 0.040 mmol) was refluxed for 1 h in 20 ml ethanol. Crystals of the title compound were obtained from an ethanol solution by slow evaporation (yield 53%; m.p. 471–472 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C17H11F3N2O2
Mr 332.28
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 7.1355 (7), 7.4786 (8), 14.8254 (18)
α, β, γ (°) 99.626 (9), 91.602 (9), 105.020 (8)
V (Å3) 751.23 (14)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.12
Crystal size (mm) 0.62 × 0.41 × 0.09
 
Data collection
Diffractometer Stoe IPDS 2
Absorption correction Integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.928, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections 10651, 3459, 1943
Rint 0.035
(sin θ/λ)max (Å−1) 0.651
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.141, 1.00
No. of reflections 3459
No. of parameters 225
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.26, −0.17
Computer programs: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data

CCDC reference: 1478497

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616007975/hb4046sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616007975/hb4046Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616007975/hb4046Isup3.cml

checkCIF report


Comment top

Schiff bases of chromone compounds are known as anticancer agents (Kawase et al., 2007, Barath et al., 2006). As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).

The dihedral angle between the ring systems (C2/C3/C4/C5/C6/C7) and (C9/C10/O1/C11-C17) is 19.19 (6)° (Fig 1). The maximum deviations belong to these ring systems are 0.012 (2)Å for atom C5 and 0.029 (2)Å for atom C17, respectively. The distance of imino group atoms, N1—C6 = 1.420 (3)Å and N1—C8 = 1.275 (3)Å are consistent with the related structures, (E)-4-[(4-chlorophenylimino)methyl]benzene-1,2,3-triol (Karabıyık et al., 2008) and (Z)-4-(((Z)-(2-Oxonaphthalen-1(2H)-ylidene)methyl)amino)-N-(thiazol-2(3H) -ylidene)benzenesulfonamide (Köysal et al., 2015). An intramolecular N2-H2A···N1 hydrogen bond (Table 2) closes an R(6) ring

In the crystal, N2—H2B···O2 hydrogen bonds (Fig. 2) link the molecules into [100] C(6) chains.

Experimental top

A mixture of a solution containing 2-amino-4-oxo-4H-chromene-3-carbaldehyde (0.0076 g 0.040 mmol) in 20 ml e thanol and a solution containing 3-(trifluoromethyl)aniline (0.0065 g, 0.040 mmol) was refluxed for 1 h in 20 ml e thanol. Crystals of the title compound were obtained from ethyl alcohol solution by slow evaporation (yield 53%; m.p. 471–472 K).

Refinement top

The H2A and H2B atoms bonded to atom N2 were freely refined. All other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å.

Structure description top

Schiff bases of chromone compounds are known as anticancer agents (Kawase et al., 2007, Barath et al., 2006). As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).

The dihedral angle between the C2–C7 and C9/C10/O1/C11–C17 ring systems is 19.19 (6)° (Fig 1); the maximum deviations are 0.012 (2) Å for atom C5 and 0.029 (2) Å for atom C17, respectively. The bond lengths of the imino group atoms [N1—C6 = 1.420 (3) Å and N1—C8 = 1.275 (3) Å] are consistent with corresponding distances in related structures, i.e. (E)-4-[(4-chlorophenylimino)methyl]benzene-1,2,3-triol (Karabıyık et al., 2008) and (Z)-4-{[(Z)-(2-oxonaphthalen-1(2H)-ylidene)methyl]amino}-N-[thiazol-2(3H) -ylidene]benzenesulfonamide (Köysal et al., 2015). An intramolecular N2—H2A···N1 hydrogen bond (Table 1) closes an R(6) ring.

In the crystal, N2—H2B···O2 hydrogen bonds (Fig. 2) link the molecules into [100] C(6) chains.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-AREA (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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed along the b axis.
2-Amino-3-((E)-{[3-(trifluoromethyl)phenyl]imino}methyl)-4H-chromen-4-one top
Crystal data top
C17H11F3N2O2Z = 2
Mr = 332.28F(000) = 340
Triclinic, P1Dx = 1.469 Mg m−3
a = 7.1355 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.4786 (8) ÅCell parameters from 10185 reflections
c = 14.8254 (18) Åθ = 2.8–28.0°
α = 99.626 (9)°µ = 0.12 mm−1
β = 91.602 (9)°T = 293 K
γ = 105.020 (8)°Blade, yellow
V = 751.23 (14) Å30.62 × 0.41 × 0.09 mm
Data collection top
Stoe IPDS 2
diffractometer		3459 independent reflections
Radiation source: fine-focus sealed tube1943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 6.67 pixels mm-1θmax = 27.6°, θmin = 2.8°
rotation method scansh = −9→9
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −9→9
Tmin = 0.928, Tmax = 0.989l = −19→19
10651 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0712P)2]
where P = (Fo2 + 2Fc2)/3
3459 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C17H11F3N2O2γ = 105.020 (8)°
Mr = 332.28V = 751.23 (14) Å3
Triclinic, P1Z = 2
a = 7.1355 (7) ÅMo Kα radiation
b = 7.4786 (8) ŵ = 0.12 mm−1
c = 14.8254 (18) ÅT = 293 K
α = 99.626 (9)°0.62 × 0.41 × 0.09 mm
β = 91.602 (9)°
Data collection top
Stoe IPDS 2
diffractometer		3459 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		1943 reflections with I > 2σ(I)
Tmin = 0.928, Tmax = 0.989Rint = 0.035
10651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.26 e Å−3
3459 reflectionsΔρmin = −0.17 e Å−3
225 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
xyzUiso*/Ueq
F11.1149 (3)1.2500 (3)1.04420 (11)0.1398 (7)
F21.3145 (3)1.3841 (3)0.96186 (14)0.1488 (8)
F31.2718 (3)1.0977 (3)0.96031 (12)0.1440 (8)
O11.00027 (15)0.60607 (17)0.39411 (8)0.0605 (3)
O20.48054 (19)0.7063 (3)0.45522 (12)0.1060 (6)
N10.9386 (2)0.9435 (2)0.64656 (11)0.0635 (4)
N21.1497 (2)0.7799 (2)0.52389 (13)0.0636 (4)
H2A1.149 (3)0.848 (3)0.5759 (15)0.067 (6)*
H2B1.257 (3)0.754 (3)0.5005 (15)0.080 (6)*
C11.1803 (4)1.2277 (3)0.96150 (17)0.0885 (7)
C21.0264 (3)1.1879 (3)0.88641 (15)0.0722 (5)
C30.8666 (3)1.2580 (3)0.90000 (16)0.0826 (6)
H30.85171.32400.95710.099*
C40.7307 (3)1.2296 (3)0.82875 (17)0.0864 (7)
H40.62421.27900.83750.104*
C50.7485 (3)1.1285 (3)0.74360 (15)0.0750 (6)
H50.65541.11170.69550.090*
C60.9068 (3)1.0518 (2)0.73012 (13)0.0628 (5)
C71.0465 (3)1.0860 (3)0.80176 (14)0.0670 (5)
H71.15531.04020.79320.080*
C80.7961 (3)0.8608 (3)0.58759 (13)0.0632 (5)
H80.67410.87460.60210.076*
C90.8082 (2)0.7480 (2)0.50068 (13)0.0578 (4)
C100.9849 (2)0.7136 (2)0.47434 (12)0.0542 (4)
C110.8380 (2)0.5221 (2)0.33411 (13)0.0590 (4)
C120.8643 (3)0.4088 (3)0.25495 (15)0.0741 (5)
H120.98660.39190.24340.089*
C130.7079 (4)0.3218 (3)0.19368 (16)0.0855 (6)
H130.72410.24600.13960.103*
C140.5251 (4)0.3453 (3)0.21125 (17)0.0893 (7)
H140.41900.28400.16950.107*
C150.5009 (3)0.4590 (3)0.29012 (16)0.0807 (6)
H150.37810.47500.30140.097*
C160.6580 (2)0.5510 (3)0.35376 (13)0.0631 (5)
C170.6385 (2)0.6731 (3)0.43930 (14)0.0682 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1402 (14)0.1950 (18)0.0741 (10)0.0447 (13)−0.0064 (9)−0.0010 (10)
F20.1259 (13)0.1278 (13)0.1574 (17)−0.0256 (11)−0.0370 (13)0.0288 (12)
F30.1729 (16)0.1383 (13)0.1233 (14)0.0840 (13)−0.0604 (12)−0.0239 (11)
O10.0469 (6)0.0706 (7)0.0674 (8)0.0237 (5)0.0074 (6)0.0090 (6)
O20.0496 (7)0.1584 (15)0.1103 (13)0.0505 (9)0.0022 (8)−0.0104 (11)
N10.0585 (9)0.0739 (9)0.0623 (10)0.0246 (7)0.0100 (7)0.0121 (8)
N20.0455 (8)0.0783 (10)0.0695 (11)0.0251 (8)0.0060 (8)0.0064 (9)
C10.0998 (17)0.0808 (15)0.0786 (17)0.0235 (14)−0.0026 (13)−0.0012 (12)
C20.0831 (13)0.0611 (11)0.0716 (13)0.0177 (10)0.0081 (10)0.0120 (10)
C30.1001 (16)0.0787 (13)0.0717 (14)0.0330 (12)0.0167 (12)0.0053 (11)
C40.0875 (15)0.0900 (15)0.0908 (17)0.0429 (12)0.0217 (13)0.0085 (13)
C50.0711 (12)0.0839 (13)0.0758 (14)0.0322 (10)0.0112 (10)0.0120 (11)
C60.0635 (11)0.0626 (10)0.0664 (12)0.0207 (9)0.0157 (9)0.0151 (9)
C70.0668 (11)0.0650 (11)0.0711 (13)0.0205 (9)0.0104 (9)0.0125 (9)
C80.0523 (10)0.0757 (11)0.0687 (12)0.0262 (9)0.0145 (9)0.0170 (10)
C90.0441 (9)0.0691 (10)0.0659 (11)0.0225 (8)0.0110 (8)0.0154 (9)
C100.0488 (9)0.0593 (9)0.0597 (10)0.0215 (8)0.0082 (8)0.0138 (8)
C110.0564 (10)0.0622 (10)0.0632 (11)0.0213 (8)0.0035 (8)0.0160 (9)
C120.0756 (12)0.0779 (12)0.0739 (13)0.0324 (10)0.0060 (11)0.0090 (11)
C130.1039 (17)0.0837 (14)0.0706 (14)0.0352 (13)−0.0045 (12)0.0043 (11)
C140.0898 (16)0.0924 (15)0.0789 (16)0.0184 (13)−0.0228 (13)0.0113 (13)
C150.0606 (11)0.0990 (15)0.0825 (15)0.0232 (11)−0.0086 (10)0.0159 (13)
C160.0513 (10)0.0724 (11)0.0686 (12)0.0192 (8)0.0007 (8)0.0180 (9)
C170.0458 (9)0.0866 (13)0.0767 (13)0.0260 (9)0.0071 (9)0.0135 (10)
Geometric parameters (Å, º) top
F1—C11.324 (3)C5—H50.9300
F2—C11.304 (3)C6—C71.380 (3)
F3—C11.302 (3)C7—H70.9300
O1—C101.344 (2)C8—C91.435 (3)
O1—C111.380 (2)C8—H80.9300
O2—C171.236 (2)C9—C101.404 (2)
N1—C81.275 (2)C9—C171.423 (3)
N1—C61.420 (2)C11—C121.375 (3)
N2—C101.302 (2)C11—C161.388 (2)
N2—H2A0.85 (2)C12—C131.365 (3)
N2—H2B0.90 (2)C12—H120.9300
C1—C21.479 (3)C13—C141.387 (3)
C2—C31.379 (3)C13—H130.9300
C2—C71.387 (3)C14—C151.369 (3)
C3—C41.365 (3)C14—H140.9300
C3—H30.9300C15—C161.395 (3)
C4—C51.386 (3)C15—H150.9300
C4—H40.9300C16—C171.466 (3)
C5—C61.399 (3)
C10—O1—C11120.17 (13)N1—C8—H8117.3
C8—N1—C6119.83 (15)C9—C8—H8117.3
C10—N2—H2A117.3 (13)C10—C9—C17119.43 (17)
C10—N2—H2B118.3 (13)C10—C9—C8121.30 (16)
H2A—N2—H2B124.4 (19)C17—C9—C8119.25 (15)
F3—C1—F2105.9 (2)N2—C10—O1112.79 (14)
F3—C1—F1105.4 (2)N2—C10—C9124.50 (17)
F2—C1—F1104.0 (2)O1—C10—C9122.71 (15)
F3—C1—C2114.44 (19)C12—C11—O1116.69 (16)
F2—C1—C2112.9 (2)C12—C11—C16122.26 (18)
F1—C1—C2113.3 (2)O1—C11—C16121.05 (16)
C3—C2—C7120.3 (2)C13—C12—C11118.85 (19)
C3—C2—C1119.7 (2)C13—C12—H12120.6
C7—C2—C1119.89 (19)C11—C12—H12120.6
C4—C3—C2119.3 (2)C12—C13—C14120.7 (2)
C4—C3—H3120.3C12—C13—H13119.7
C2—C3—H3120.3C14—C13—H13119.7
C3—C4—C5121.1 (2)C15—C14—C13119.9 (2)
C3—C4—H4119.4C15—C14—H14120.0
C5—C4—H4119.4C13—C14—H14120.0
C4—C5—C6119.8 (2)C14—C15—C16120.8 (2)
C4—C5—H5120.1C14—C15—H15119.6
C6—C5—H5120.1C16—C15—H15119.6
C7—C6—C5118.56 (18)C11—C16—C15117.49 (19)
C7—C6—N1116.63 (16)C11—C16—C17119.89 (16)
C5—C6—N1124.79 (18)C15—C16—C17122.62 (17)
C6—C7—C2120.72 (18)O2—C17—C9123.26 (19)
C6—C7—H7119.6O2—C17—C16120.15 (18)
C2—C7—H7119.6C9—C17—C16116.60 (15)
N1—C8—C9125.45 (16)
F3—C1—C2—C3150.4 (2)C8—C9—C10—N2−0.8 (3)
F2—C1—C2—C3−88.4 (3)C17—C9—C10—O1−2.5 (3)
F1—C1—C2—C329.6 (3)C8—C9—C10—O1178.87 (16)
F3—C1—C2—C7−31.8 (3)C10—O1—C11—C12−177.75 (16)
F2—C1—C2—C789.4 (3)C10—O1—C11—C162.0 (2)
F1—C1—C2—C7−152.7 (2)O1—C11—C12—C13179.66 (19)
C7—C2—C3—C4−1.4 (3)C16—C11—C12—C13−0.1 (3)
C1—C2—C3—C4176.3 (2)C11—C12—C13—C14−0.7 (3)
C2—C3—C4—C51.3 (4)C12—C13—C14—C151.0 (4)
C3—C4—C5—C60.8 (3)C13—C14—C15—C16−0.4 (4)
C4—C5—C6—C7−2.7 (3)C12—C11—C16—C150.6 (3)
C4—C5—C6—N1178.99 (19)O1—C11—C16—C15−179.16 (18)
C8—N1—C6—C7159.66 (18)C12—C11—C16—C17179.95 (18)
C8—N1—C6—C5−22.0 (3)O1—C11—C16—C170.2 (3)
C5—C6—C7—C22.5 (3)C14—C15—C16—C11−0.3 (3)
N1—C6—C7—C2−179.00 (17)C14—C15—C16—C17−179.7 (2)
C3—C2—C7—C6−0.5 (3)C10—C9—C17—O2−175.6 (2)
C1—C2—C7—C6−178.25 (19)C8—C9—C17—O23.0 (3)
C6—N1—C8—C9179.79 (18)C10—C9—C17—C164.4 (3)
N1—C8—C9—C102.3 (3)C8—C9—C17—C16−176.88 (17)
N1—C8—C9—C17−176.31 (19)C11—C16—C17—O2176.7 (2)
C11—O1—C10—N2178.83 (15)C15—C16—C17—O2−4.0 (3)
C11—O1—C10—C9−0.9 (2)C11—C16—C17—C9−3.4 (3)
C17—C9—C10—N2177.86 (18)C15—C16—C17—C9175.96 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.85 (2)2.06 (2)2.727 (2)134.4 (16)
N2—H2B···O2i0.90 (2)1.84 (2)2.745 (2)178 (2)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.85 (2)2.06 (2)2.727 (2)134.4 (16)
N2—H2B···O2i0.90 (2)1.84 (2)2.745 (2)178 (2)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H11F3N2O2
Mr332.28
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.1355 (7), 7.4786 (8), 14.8254 (18)
α, β, γ (°)99.626 (9), 91.602 (9), 105.020 (8)
V (Å3)751.23 (14)
Z2
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.62 × 0.41 × 0.09
Data collection
DiffractometerStoe IPDS 2
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.928, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		10651, 3459, 1943
Rint0.035
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.141, 1.00
No. of reflections3459
No. of parameters225
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.26, −0.17

Computer programs: X-AREA (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

 

Acknowledgements

The authors wish to 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

First citationBarath, Z., Radices, R., Spengler, G., Ocsovski, I., Kawase, M., Motohashi, N., Shirataki, Y., Shah, A. & Molnar, J. (2006). In Vivo, 20, 645–000.  PubMed CAS Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationKarabıyık, H., Ocak-Ískeleli, N., Petek, H., Albayrak, C. & Ağar, E. (2008). J. Mol. Struct. 873, 130–136.  Google Scholar
 First citationKawase, M., Tanaka, T., Kan, H., Tani, S., Nakashima, H. & Sakagami, H. (2007). In Vivo, 21, 829–834.  Web of Science PubMed CAS Google Scholar
 First citationKöysal, Y., Bülbül, H., Dege, N., Macit, M. & Alaman, A. A. (2015). Crystallogr. Rep. 60, 1001–1005.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 5| May 2016| x160797
doi:10.1107/S2414314616007975
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