Literature DB >> 23424451

1-{(Z)-[2-Meth-oxy-5-(trifluoro-meth-yl)anilino]methyl-idene}naphthalen-2(1H)-one.

Hakan Kargılı1, Ayşen Alaman Ağar, Gökhan Alpaslan, Orhan Büyükgüngör, Ahmet Erdönmez.   

Abstract

The title compound, C(19)H(14)F(3)NO(2), crystallizes in the keto-amine tautomeric form, with a strong intra-molecular N-H⋯O hydrogen bond. The mol-ecule is almost planar; the dihedral angle between the naphthalene ring system and the benzene ring is 4.60 (7)°. In the crystal, mol-ecules are linked into chains along the c axis by C-H⋯O hydrogen bonds. The F atoms of the trifluoro-methyl group are disordered over two positions with refined site occupancies of 0.668 (9) and 0.332 (9).

Entities:  

Year:  2013        PMID： 23424451      PMCID： PMC3569228          DOI： 10.1107/S1600536812051410

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For Schiff base tautomerism, see: Hökelek et al. (2000 ▶); Odabaşoğlu et al. (2005 ▶). For related strucures, see: Özek et al. (2004 ▶); Temel et al. (2010 ▶).

Experimental

Crystal data

C19H14F3NO2 M = 345.31 Monoclinic, a = 16.3922 (10) Å b = 5.7201 (2) Å c = 17.7632 (10) Å β = 106.284 (5)° V = 1598.75 (14) Å3 Z = 4 Mo Kα radiation μ = 0.12 mm−1 T = 296 K 0.58 × 0.35 × 0.13 mm

Data collection

Stoe IPDSII diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.949, T max = 0.984 19794 measured reflections 3129 independent reflections 1722 reflections with I > 2σ(I) R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.097 S = 0.95 3129 reflections 258 parameters 72 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.15 e Å−3 Δρmin = −0.17 e Å−3 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051410/fy2084sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051410/fy2084Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812051410/fy2084Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H14F3NO2F(000) = 712
Mr = 345.31Dx = 1.435 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15281 reflections
a = 16.3922 (10) Åθ = 1.5–28.0°
b = 5.7201 (2) ŵ = 0.12 mm−1
c = 17.7632 (10) ÅT = 296 K
β = 106.284 (5)°Prism, brown
V = 1598.75 (14) Å30.58 × 0.35 × 0.13 mm
Z = 4
Stoe IPDSII diffractometer3129 independent reflections
Radiation source: fine-focus sealed tube1722 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.4°
ω scansh = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −7→7
Tmin = 0.949, Tmax = 0.984l = −21→21
19794 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 0.95w = 1/[σ2(Fo2) + (0.0399P)2] where P = (Fo2 + 2Fc2)/3
3129 reflections(Δ/σ)max < 0.001
258 parametersΔρmax = 0.15 e Å−3
72 restraintsΔρmin = −0.17 e Å−3
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.
xyzUiso*/UeqOcc. (<1)
C10.17645 (13)0.2354 (4)0.18859 (12)0.0443 (6)
C20.15233 (15)0.1866 (5)0.10590 (13)0.0527 (6)
C30.10170 (16)−0.0181 (5)0.07934 (13)0.0589 (7)
H30.0853−0.05300.02610.071*
C40.07736 (15)−0.1601 (5)0.12881 (13)0.0573 (7)
H40.0450−0.29130.10880.069*
C50.09943 (13)−0.1173 (4)0.21140 (13)0.0459 (6)
C60.07423 (15)−0.2706 (4)0.26206 (14)0.0568 (6)
H60.0436−0.40410.24170.068*
C70.09358 (16)−0.2288 (5)0.34056 (14)0.0625 (7)
H70.0765−0.33260.37350.075*
C80.13909 (17)−0.0297 (5)0.37078 (13)0.0611 (7)
H80.15190.00100.42420.073*
C90.16550 (15)0.1225 (4)0.32305 (12)0.0543 (6)
H90.19600.25500.34470.065*
C100.14750 (13)0.0831 (4)0.24208 (12)0.0424 (5)
C110.22965 (14)0.4238 (4)0.21675 (13)0.0466 (6)
H110.24490.45300.27040.056*
C120.31391 (14)0.7553 (4)0.19682 (13)0.0470 (6)
C130.33425 (15)0.8888 (4)0.13842 (13)0.0518 (6)
C140.38600 (16)1.0818 (5)0.15828 (15)0.0611 (7)
H140.39951.16960.11940.073*
C150.41778 (15)1.1448 (5)0.23597 (16)0.0616 (7)
H150.45251.27570.24920.074*
C160.39861 (15)1.0159 (4)0.29414 (14)0.0526 (6)
C170.34681 (14)0.8209 (4)0.27413 (13)0.0531 (6)
H170.33410.73300.31340.064*
C180.43282 (19)1.0816 (6)0.37746 (17)0.0706 (8)
C190.3127 (2)0.9460 (5)0.00083 (15)0.0800 (9)
H19A0.28530.8708−0.04800.120*
H19B0.37250.95780.00660.120*
H19C0.28931.09970.00140.120*
F1A0.3844 (4)1.0304 (15)0.4230 (2)0.112 (2)0.668 (9)
F2A0.5162 (2)1.0948 (14)0.3989 (3)0.1156 (18)0.668 (9)
F3A0.4413 (6)1.3154 (9)0.3887 (3)0.139 (2)0.668 (9)
F1B0.4342 (10)0.897 (2)0.4242 (4)0.108 (4)0.332 (9)
F2B0.4937 (8)0.945 (3)0.4172 (5)0.113 (4)0.332 (9)
F3B0.3934 (8)1.252 (3)0.3936 (6)0.126 (5)0.332 (9)
N10.25997 (12)0.5641 (3)0.17194 (11)0.0489 (5)
O10.17545 (12)0.3149 (3)0.05715 (9)0.0707 (5)
O20.29915 (11)0.8115 (3)0.06414 (9)0.0651 (5)
H10.2375 (18)0.521 (5)0.1153 (17)0.100 (10)*
U11U22U33U12U13U23
C10.0468 (13)0.0434 (15)0.0421 (12)0.0046 (11)0.0116 (10)0.0010 (11)
C20.0547 (14)0.0570 (16)0.0451 (13)0.0073 (13)0.0120 (11)0.0037 (13)
C30.0589 (16)0.0727 (19)0.0403 (12)0.0039 (14)0.0064 (11)−0.0073 (13)
C40.0540 (15)0.0602 (17)0.0557 (15)−0.0027 (13)0.0117 (12)−0.0125 (13)
C50.0426 (13)0.0439 (14)0.0516 (13)0.0045 (11)0.0141 (10)−0.0030 (11)
C60.0534 (15)0.0492 (16)0.0699 (16)−0.0039 (12)0.0207 (13)−0.0024 (13)
C70.0706 (17)0.0593 (18)0.0631 (16)−0.0044 (15)0.0281 (13)0.0099 (14)
C80.0710 (17)0.0699 (19)0.0436 (13)−0.0054 (15)0.0179 (12)0.0046 (13)
C90.0596 (15)0.0574 (17)0.0458 (13)−0.0090 (13)0.0144 (11)−0.0018 (12)
C100.0391 (12)0.0447 (14)0.0431 (12)0.0036 (11)0.0113 (9)0.0015 (11)
C110.0485 (13)0.0489 (15)0.0447 (12)0.0066 (12)0.0167 (11)0.0070 (12)
C120.0470 (13)0.0420 (14)0.0551 (14)0.0081 (12)0.0195 (11)0.0077 (12)
C130.0521 (14)0.0543 (17)0.0534 (15)0.0044 (12)0.0221 (12)0.0049 (12)
C140.0652 (16)0.0610 (18)0.0643 (17)−0.0004 (15)0.0298 (13)0.0125 (14)
C150.0542 (16)0.0566 (17)0.0786 (18)−0.0081 (13)0.0259 (14)0.0024 (15)
C160.0476 (14)0.0523 (16)0.0598 (15)−0.0011 (12)0.0180 (11)0.0005 (13)
C170.0549 (14)0.0540 (16)0.0538 (14)0.0009 (13)0.0206 (12)0.0088 (12)
C180.065 (2)0.070 (2)0.077 (2)−0.0131 (18)0.0216 (16)−0.0105 (18)
C190.099 (2)0.090 (2)0.0601 (16)−0.0002 (18)0.0382 (15)0.0151 (16)
F1A0.114 (3)0.164 (5)0.0654 (19)−0.055 (3)0.036 (2)−0.023 (2)
F2A0.072 (2)0.171 (5)0.091 (2)−0.037 (3)0.0024 (16)−0.023 (3)
F3A0.222 (6)0.094 (3)0.104 (3)−0.050 (4)0.048 (4)−0.029 (2)
F1B0.144 (8)0.118 (6)0.058 (3)−0.058 (6)0.024 (5)0.008 (4)
F2B0.086 (6)0.154 (8)0.080 (5)0.052 (6)−0.006 (4)−0.029 (5)
F3B0.129 (7)0.140 (9)0.100 (5)0.047 (6)0.018 (5)−0.061 (6)
N10.0534 (12)0.0474 (13)0.0470 (11)0.0008 (10)0.0156 (9)0.0033 (10)
O10.0933 (14)0.0756 (13)0.0442 (9)−0.0021 (11)0.0208 (9)0.0103 (9)
O20.0776 (12)0.0706 (13)0.0525 (10)−0.0053 (10)0.0273 (9)0.0083 (9)
C1—C111.388 (3)C12—C131.402 (3)
C1—C21.437 (3)C13—O21.357 (3)
C1—C101.463 (3)C13—C141.377 (3)
C2—O11.272 (3)C14—C151.379 (3)
C2—C31.436 (3)C14—H140.9300
C3—C41.337 (3)C15—C161.376 (3)
C3—H30.9300C15—H150.9300
C4—C51.430 (3)C16—C171.387 (3)
C4—H40.9300C16—C181.477 (4)
C5—C61.399 (3)C17—H170.9300
C5—C101.411 (3)C18—F3B1.248 (8)
C6—C71.362 (3)C18—F2B1.308 (8)
C6—H60.9300C18—F1A1.315 (4)
C7—C81.385 (3)C18—F2A1.315 (4)
C7—H70.9300C18—F1B1.339 (8)
C8—C91.367 (3)C18—F3A1.354 (5)
C8—H80.9300C19—O21.430 (3)
C9—C101.403 (3)C19—H19A0.9600
C9—H90.9300C19—H19B0.9600
C11—N11.322 (3)C19—H19C0.9600
C11—H110.9300F2A—F3A1.735 (10)
C12—C171.379 (3)F1B—F2B1.05 (2)
C12—N11.398 (3)N1—H11.00 (3)
C11—C1—C2119.0 (2)C13—C14—C15119.9 (2)
C11—C1—C10120.90 (19)C13—C14—H14120.0
C2—C1—C10120.1 (2)C15—C14—H14120.0
O1—C2—C3120.1 (2)C16—C15—C14120.7 (2)
O1—C2—C1122.3 (2)C16—C15—H15119.7
C3—C2—C1117.5 (2)C14—C15—H15119.7
C4—C3—C2122.1 (2)C15—C16—C17119.4 (2)
C4—C3—H3119.0C15—C16—C18120.9 (3)
C2—C3—H3119.0C17—C16—C18119.7 (2)
C3—C4—C5122.3 (2)C12—C17—C16121.0 (2)
C3—C4—H4118.9C12—C17—H17119.5
C5—C4—H4118.9C16—C17—H17119.5
C6—C5—C10119.6 (2)F3B—C18—F2B135.2 (6)
C6—C5—C4121.1 (2)F1A—C18—F2A126.4 (4)
C10—C5—C4119.2 (2)F3B—C18—F1B113.3 (7)
C7—C6—C5121.5 (2)F2B—C18—F1B46.8 (11)
C7—C6—H6119.3F1A—C18—F3A100.6 (4)
C5—C6—H6119.3F2A—C18—F3A81.1 (6)
C6—C7—C8119.1 (2)F3B—C18—C16110.7 (5)
C6—C7—H7120.4F2B—C18—C16114.0 (4)
C8—C7—H7120.4F1A—C18—C16115.8 (3)
C9—C8—C7120.9 (2)F2A—C18—C16112.1 (3)
C9—C8—H8119.6F1B—C18—C16110.9 (4)
C7—C8—H8119.6F3A—C18—C16113.2 (4)
C8—C9—C10121.4 (2)O2—C19—H19A109.5
C8—C9—H9119.3O2—C19—H19B109.5
C10—C9—H9119.3H19A—C19—H19B109.5
C9—C10—C5117.4 (2)O2—C19—H19C109.5
C9—C10—C1123.9 (2)H19A—C19—H19C109.5
C5—C10—C1118.73 (19)H19B—C19—H19C109.5
N1—C11—C1124.0 (2)C18—F2A—F3A50.4 (3)
N1—C11—H11118.0C18—F3A—F2A48.5 (3)
C1—C11—H11118.0F2B—F1B—C1865.0 (8)
C17—C12—N1124.3 (2)F1B—F2B—C1868.1 (8)
C17—C12—C13118.8 (2)C11—N1—C12126.6 (2)
N1—C12—C13116.9 (2)C11—N1—H1111.3 (17)
O2—C13—C14125.0 (2)C12—N1—H1122.1 (17)
O2—C13—C12114.7 (2)C13—O2—C19118.2 (2)
C14—C13—C12120.3 (2)
C11—C1—C2—O1−2.7 (3)C18—C16—C17—C12180.0 (2)
C10—C1—C2—O1179.5 (2)C15—C16—C18—F3B76.5 (10)
C11—C1—C2—C3176.1 (2)C17—C16—C18—F3B−103.8 (10)
C10—C1—C2—C3−1.7 (3)C15—C16—C18—F2B−106.0 (11)
O1—C2—C3—C4178.8 (2)C17—C16—C18—F2B73.6 (11)
C1—C2—C3—C4−0.1 (3)C15—C16—C18—F1A149.0 (5)
C2—C3—C4—C50.5 (4)C17—C16—C18—F1A−31.4 (6)
C3—C4—C5—C6−179.0 (2)C15—C16—C18—F2A−55.9 (5)
C3—C4—C5—C100.9 (3)C17—C16—C18—F2A123.7 (5)
C10—C5—C6—C71.3 (3)C15—C16—C18—F1B−156.9 (9)
C4—C5—C6—C7−178.7 (2)C17—C16—C18—F1B22.8 (10)
C5—C6—C7—C80.1 (4)C15—C16—C18—F3A33.6 (6)
C6—C7—C8—C9−0.8 (4)C17—C16—C18—F3A−146.8 (5)
C7—C8—C9—C100.1 (4)F3B—C18—F2A—F3A−17.8 (9)
C8—C9—C10—C51.3 (3)F2B—C18—F2A—F3A−145.9 (6)
C8—C9—C10—C1−177.9 (2)F1A—C18—F2A—F3A−96.6 (6)
C6—C5—C10—C9−2.0 (3)F1B—C18—F2A—F3A−135.1 (6)
C4—C5—C10—C9178.0 (2)C16—C18—F2A—F3A111.5 (4)
C6—C5—C10—C1177.3 (2)F3B—C18—F3A—F2A154.8 (11)
C4—C5—C10—C1−2.7 (3)F2B—C18—F3A—F2A27.3 (7)
C11—C1—C10—C94.5 (3)F1A—C18—F3A—F2A125.6 (4)
C2—C1—C10—C9−177.7 (2)F1B—C18—F3A—F2A83.5 (10)
C11—C1—C10—C5−174.70 (19)C16—C18—F3A—F2A−110.3 (4)
C2—C1—C10—C53.1 (3)F3B—C18—F1B—F2B−131.0 (8)
C2—C1—C11—N10.2 (3)F1A—C18—F1B—F2B−149.5 (8)
C10—C1—C11—N1178.1 (2)F2A—C18—F1B—F2B−10.6 (7)
C17—C12—C13—O2180.0 (2)F3A—C18—F1B—F2B−89.7 (11)
N1—C12—C13—O2−0.8 (3)C16—C18—F1B—F2B103.9 (6)
C17—C12—C13—C14−0.1 (3)F3B—C18—F2B—F1B79.9 (17)
N1—C12—C13—C14179.0 (2)F1A—C18—F2B—F1B22.7 (7)
O2—C13—C14—C15179.6 (2)F2A—C18—F2B—F1B165.1 (10)
C12—C13—C14—C15−0.2 (4)F3A—C18—F2B—F1B126.0 (8)
C13—C14—C15—C160.3 (4)C16—C18—F2B—F1B−96.7 (8)
C14—C15—C16—C170.0 (4)C1—C11—N1—C12−179.7 (2)
C14—C15—C16—C18179.6 (2)C17—C12—N1—C112.8 (3)
N1—C12—C17—C16−178.7 (2)C13—C12—N1—C11−176.3 (2)
C13—C12—C17—C160.4 (3)C14—C13—O2—C19−3.5 (3)
C15—C16—C17—C12−0.4 (3)C12—C13—O2—C19176.4 (2)
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i0.932.513.423 (3)166
N1—H1···O11.00 (3)1.70 (3)2.554 (3)140 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C8—H8⋯O1i 0.932.513.423 (3)166
N1—H1⋯O11.00 (3)1.70 (3)2.554 (3)140 (2)

Symmetry code: (i) .

  5 in total

1.  Bacteriorhodopsin: a light-driven proton pump in Halobacterium Halobium.

Authors:  R H Lozier; R A Bogomolni; W Stoeckenius
Journal:  Biophys J       Date:  1975-09       Impact factor: 4.033

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  1-[(E)-(2-Phenoxy-anilino)methyl-ene]naphthalen-2(1H)-one.

Authors:  Ersin Temel; Erbil Ağar; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-21

4.  {6,6'-Dieth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II) monohydrate.

Authors:  Hadi Kargar; Arezoo Jamshidvand; Hoong-Kun Fun; Reza Kia
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-14

5.  {6,6'-Dimeth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II) 1.78-hydrate.

Authors:  Chin Sing Yeap; Reza Kia; Hadi Kargar; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-25
  5 in total
  1 in total

1.  A handy and accessible tool for identification of Sn(II) in toothpaste.

Authors:  Shampa Kundu; Khai-Nghi Truong; Shrabani Saha; Kari Rissanen; Prithidipa Sahoo
Journal:  Sci Rep       Date:  2022-02-10       Impact factor: 4.379
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.